See Now, Buy Now: The Timex Weekender Chrono Is Your Next Casual, Everyday Watch

A heck of a versatile, casual watch from our good friends at Timex.

Join us for the second entry this week (!) in our See Now, Buy Now series, my friends. To start: Last month, we talked on The Style Guide about a rugged casual timepiece to stand up to the bolder, heartier textures of winter. Seeing as we’re now cruising right through March, it’s now only fitting to talk about a stylish casual timepiece that can suitably blend in with textured, yet breezier outfits for spring months. That timepiece, my friends, would be the Timex Weekender Chrono, featuring a slightly oversized face, a textured NATO strap (crucial) and a spring-friendly color combo. Timex is certainly a consistent favorite on the blog, all thanks to that critical blend of affordability and style that hits right down the middle of the fairway. The design details are sharp when it comes to the Timex Weekender Chrono, too.  The date feature and a chronograph that tracks down to 1/20th of a second are handy extra features, as is the INDIGLO nightlight. And stylistically? The Timex Weekender Chrono has all the chops you need when it comes to dressing for laidback spring style scenarios.

A casual BBQ spent wearing one of the best pairs of men’s shorts for spring and summer? Throw the Timex Weekender Chrono on alongside some classic Aviators and a short-sleeve henley. A casual day at the office works for the Weekender Chrono, too. Think a navy blazer, chinos and white sneakers — it’s as simple as that. And when you want to throw on that standby weekend uniform (a classic chambray shirt, dark denim and rugged suede chukkas), the Timex Weekender Chrono is there for you, buddy. The olive green NATO strap nods toward spring without going full-on floral (although I myself have a neat patterned watch strap from The Knottery — throwback!). At any rate, an olive NATO strap has real-life military heritage roots, plus a bit of versatile color to pair up with dark denim, classic chinos or chambray shorts. I’d certainly take the chance to wear the Timex Weekender Chrono as often as possible.

Is the Timex Weekender Chrono set to join your collection of Timex watches? Let me know in the comments! 

Style Suggestion: Wear This Casual Outfit to Work Remotely

OK, step right on up — we’re talking today on The Style Guide about a somewhat difficult style conundrum that seems to be popping up more often in today’s economy of the 21st century. To get right to the point: We’re covering the best #menswear to wear to work remotely — so, how to dress for comfort and style when working from home, working on the road or working from your favorite Brooklyn coffee shop (as I so often do on weekends and my days off from the old day job).  One thing is clear — you need plenty of the best men’s gear to keep you going. And what are my top picks (and possibly yours, too)?The trick is to keep it simple, stylish and certatinly not sloppy. Think a bit like a business casual look, yet … more casual. And yes, even if you’re not in the office, dressing a bit better ramps up your focus and productivity just a bit. Let’s start with a classic Oxford shirt and team it with other reliable basics — slim grey chinos, a trusty pair of classic suede chukka boots and other favorites — including a timeless leather watch and plenty more.  Are you ready? Let’s gear up to get to work. Chime in with your thoughts on this #OOTD on Twitter, and catch my daily ensembles on Instagram. Thanks for reading!

The Shirt: Flint and Tinder Texas-Made Oxford in White — $89

Flint and Tinder

A crisp, classic and clean white Oxford — great even for working from a coffee shop.

The great folks at Flint and Tinder do so many things so well, and you can now add a stylish Oxford shirt to that offering.  There’s a reason the classic Oxford shirt is a menswear staple — it’s among the men’s shirts out there, it’s timeless and it looks great on every guy. It also adds some needed polish to even the most laidback of ensembles — I’m not saying you can wear it with slim sweatpants, but I am saying it’ll clean up in a jiffy if you need to throw on a navy blazer to head to an unexpected meeting as you work remotely. Plus, it’ll work stylishly through all four seasons. Not bad at all, ehh?

The Tee: Outerknown Pagoda Stripe Tee — $53.98


A reliable tee that’ll work nicely for layering — and sustainable style.

In the name of adding visual interest to your white Oxford shirt, we’re throwing on a slim striped tee underneath. It serves a dual purpose — coffee shops can be a bit chilly if the A/C is blasting, so a tee helps add both comfort and style. Oh, and since it’s from Outerknown, your purchase of this tee champions the brand’s mission of sustainable style. First seen in a Style Pick of the Week entry, this pleasingly textured shirt is a reliable second layer — you can even ditch the shirt and wear only the Outerknown Pagoda Stripe Tee (which I’d also support).

The Mid-Layer: Life/After/Denim Awash Hoodie in Dark Blue — $80


Absolutely more than a hoodie — absolutely the nicest hooded sweatshirt you’ll buy.

As we mentioned above, coffee shops can get a tad chilly. And if you happen to be holed up working away, you might just want another layer to keep you cool and comfortable (you’ll hear that word a lot in this post). We’re not just throwing on a ratty hoodie and calling it a day, though. Life/After/Denim takes everyday basics for the stylish guy and amps them up a bit, focusing on excellent fabrics and just-right construction. That’s what makes the Awash Hoodie such a neat buy — it’s a refined hoodie that wouldn’t look out of place over a classic Oxford.

The Pants: Outerknown Ditch Crop Pants — $99.98


A pair of laidback, casual-yet-stylish chino pants that work for everyday wear.

Once again, Outerknown pops up in this style suggestion, partly due to the brand’s emphasis on easygoing-yet-sharp styles and partly due to its commitment to sustainability.  Both are important to consider, and it should make purchasing the Outerknown Ditch Crop Pants that much easier.  The versatile grey color goes with just about any off-duty style combo you can dream up, while the tapered and cropped fit offers more room to show off your classic suede chukka boots. Speaking of…


The Boots: Astorflex Greenflex in Dark Chestnut — $145


A wear-with-anything set of chukkas that’ll look better than plain sneakers.

We here at The Style Guide love our versatile chukka boots –any time of the year. Bear with me — this particular pair, made sustainably by Astorflex, incorporates plenty of comfort and a very wearable silhouette. They’re timeless and laidback, easy to take on and off, and polished enough to team up with more refined pieces in a hurry. And they provide a nice, earthy contrast to the slim grey chino pants and white Oxford.  There’s certainly a lot to like — no, love — about the Astorflex Greenflex.

The Socks: Arvin Goods Casual Socks (Three-pack) — $36

Arvin Goods

Well-made socks that are far from flashy — just what you need to work outside the office for the day.

Fear not, my fellow menswear lovers. We’ve got you covered right down to the socks today. When your outfit is composed of casual basics, from suede chukkas on up to a slim striped tee, socks might be seen as an afterthought. Not so fast, my friend.  Made in a simple grey-and-red color combo from lightweight fabric, these Arvin Goods Casual Socks won’t slip down your legs throughout the day — and they’ll provide a bit of color in terms of your overall outfit. Nothing too flashy, though. Sounds like a winner on all fronts.


The Watch: Timex Weekender Chrono in Brown Leather — $82

Timex Weekender

Nothing overly fancy about a well-made, tough Timex watch. Just the right pick for this outfit.

As with the rest of this ensemble, the “less is more” approach works out quite nicely. So, we’re ditching a flashy watch for something casual, low-key and distinctly stylish. And it frequently seems to be the case that the Timex Weekender is the right watch to pick for those types of circumstances. Featuring handy chronograph functionality and a rich brown leather strap, the Timex Weekender Chrono should be your go-to watch for when you want to feel casual, yet look sharp.

The Belt: Line of Trade Veg-Tanned Leather Belt — $55 ($40 When Signing up for Bespoke Post)

Line of Trade

A rugged, well-crafted belt to complement those light grey chinos.

Leave no stone unturned when it comes time to put together a stylish outfit to wear when working remotely. This Line of Trade belt is handsome, rugged and very well-made. It’ll age beautifully the more you wear it, and it’ll stylishly complement that classic Timex watch — whether you’re at your favorite coffee shop or the nearest Starbucks (happens to the best of us).

Frank And Oak

The Essentials: Filson Pullman Bag — $420.98 AND Tactile Turn Brass Slider Pen — $59


Two picks that could feasibly go everywhere with you. Definitely add them to your daily haul.

We were just talking about leaving no stone unturned when gearing up to work remotely, and you certainly need the right goods to get the job done. The recognizable, heritage-quality Filson Pullman Bag is a durable, tough and stylish pick to haul around your everyday carry (plus, it fits with the rugged-casual nature of this outfit). And a good pen — with great writing quality — is an underrated desk essential. Make sure the Tactile Turn Brass Slider is in your bag.

The Laptop Carrier: This Is Ground Mod 15-Inch Laptop Carrier — $419.98


Designed and sized to carry everything you could possibly need for a day of work.

There’s nothing you want less when working remotely than to realize you forgot something essential. That’s where the ridiculously handy and well-made This Is Ground Mod Laptop Carrier comes into play. It’s priced on the high side (to say the least), but it’s worth it. Sized to help you haul just about everything you might need to work remotely, it comes in a handsome shade of French Grey, the Mod Laptop Carrier features plenty of space for your phone, your laptop and a plethora of pens and office supplies. It’s practically a must-buy.

The Wallet: Jack Mason Leather Front Pocket Wallet — $95 ($70 When Signing up for Bespoke Post)

Jack Mason

The slim wallet that you’ve been looking for — ideal for slipping into your bag as you head out to get some work done.

Particularly when working away from the office, the daily essentials take on that much  more significance. Which is to say: You don’t want to be caught without your wallet. The handsome, meticulously crafted Jack Mason Leather Front Pocket Wallet solves that problem easily, what with its rich leather and easy accessibility from the front (or back) pocket of your Outerknown chinos.

The Headphones: Marshall Major II On-Ear Headphones — $100

Nothing beats great tunes and a little peace, quiet and … freelance work?

To be fair, not everyone likes to listen to music when working. Ladies and gentlemen … I am not one of those people. Let’s upgrade your listening experience in terms of both style and quality, though — shall we? Marshall on-ear headphones are high-quality and distinctive — and what’s more, they’ll provide a neat complement to your home listening experience as well as when you work remotely. They’re well-priced, too. That’s a heck of a lot of positives to consider, no?

There are certainly challenges inherent when it comes to dressing to work remotely. You need to consider comfort and style in equal measure — two areas that can sometimes be difficult to match up. I think you’ll find a classic Oxford shirt, like the Flint and Tinder piece featured here, helps out. As far as your basics go, the Outerknown Ditch Crop Pants  provide easy wearability when matched up with classic suede chukka boots. And essential accessories — from a rugged leather watch to a stylish Filson bag — are going to make your remote work that much more enjoyable (and timely).  Don’t forget to keep your laptop safe with the investment-worthy This Is Ground Mod Laptop Carrier. As far as musical accompaniment to your day, I’d also urge you to snap up the Marshall Major II On-Ear Headphones.  Again, there’s certainly a lot of gear — and quite a few variables — to keep in mind when working remotely, especially if you want to look (and feel!) your best. With that being said — what do you think of this list? Let me know in the comments below!

Thanks so much for reading,


#OOTD: How to Dress Casually This Winter

We’re a month into the new year, and the question for all of us #menswear fans has to be: Are you sticking to your men’s style resolutions? Finding ways to improve your wardrobe and upgrade your style? Hopefully, that’s the case through these first few weeks of 2017 — and it’s that same approach that should apply to even seemingly casual, daily style. We’ve talked tailored winter style, we’ve talked classic winter style and now, we’re talking about a style situation that can sometimes be a difficult balance — casual winter style. For those times you want to be relaxed and comfortable, yet put-together. Even if you’re only making a quick morning coffee run or an evening beer run before hosting friends, putting your best foot forward is, as we always talk about at The Style Guide, crucial. So, we’re taking staple pieces of your wardrobe and switching them up a bit — a classic black jacket, sharp denim and your favorite pair of leather boots, for starters.  Read and shop the below #OOTD,  leave questions in the comments section below, and follow along on Instagram for more daily winter style inspiration.  Good luck out there!

Taking basic pieces and amping them up with improved fits, great fabric and yes, great style

Taking basic pieces and amping them up with improved fits, great fabric and yes, great style.

The Jacket: Reigning Champ Trail Jacket, $198.98 — Lest you think that this Trail Jacket is basic, its performance and classic silhouette speak for itself (namely, the terry cotton and nylon combo is functional and easily wearable).

The Henley: Faherty Brand Waffle Henley Sweater, $154.98 — Part henley, part sweater and a substantial upgrade from your standard weekend T-shirt — warm, cozy, ultra-stylish and yes, pricey.

The Denim: Abercrombie & Fitch Slim-Straight Performance Winter Jeans, $35.20 — Is there such a thing as winter denim? There certainly is — and for a great price, you’re getting excellent comfort, a tremendous fit and comfortable fabric.

The Hat: Ebbets Field Flannels for J. Crew Detroit Cubs Ballcap, $49.50 — A ballcap in this instance? Absolutely — we’re going for casual style after all, and this hat is a unique, vintage-inspired conversation starter.

The Boots: CAT Footwear Sutter Boots, $210 —  While you could always swap in a pair of handsome leather sneakers, tough leather boots are the way to go in the snow — plus, they add a bit of sharpness to this casual look.

The Socks: Richer Poorer Stitcher Classic Boot Sock, $16 — Comfort, quality and a bit of sport-inspired style — that’s what you’re getting with these crisp boot socks.

The Belt: Abercrombie & Fitch Woven Leather Belt, $30.80 — Add some seasonally appropriate texture and casual style with this nicely priced, versatile leather belt. Wear it with slim chinos and a navy blazer to the office, too.
Beckett Simonon

The Watch: Timex Weekender Chrono Oversized, $84.95 — It’s tough to beat the reliability, durability and simple style of a Timex watch for the price. You could also go with the sharp Form-Function-Form Horween Leather Weekender here.

The Briefcase: Joshu + Vela Zip Briefcase, $265 — Be it lugging around your laptop or your everyday carry, you need a great bag. The Joshu + Vela Zip Briefcase is handsome, beautifully made and durable — just what you need.

That’s a wrap on this week’s #OOTD — although it’s sometimes easy to let your style slip up in casual situations, resist the temptation to do so with functional, comfortable pieces that fit, feel and look great. Starting with the technical-yet-sharp Reigning Champ Trail Jacket and continuing with reliable layering pieces like the Waffle Henley Sweater, you’ll be set in terms of warmth and versatility. Brushed cotton denim and tough leather boots hardly ever fail, and they’re a nice way to complement more casual accessories, like that vintage-inspired J. Crew ballcap and Timex watch.  And no matter the occasion, a reliable bag like the Joshu + Vela Zip Briefcase  is the perfect way to carry your gear from point A to point B. OK, got all that? You bet.

Thanks for reading and stay stylish,


#OOTD: How to Dress for a Rainy Spring Day

Editor’s note: You’ve surely seen this hashtag lots of different places, including on Instagram. But how does that carry over to real life? The #OOTD series will take one great item and put together a versatile, stylish outfit around it. Look for past features here.

If you’ve been keeping up with the #OOTD series here on The Style Guide, you might notice that the outfits as of late have leaned more casual (if a tailored look is what you seek, head here). Perhaps it’s the shifting climate that has this menswear writer more geared toward shorts, perhaps it’s the effects of a stylish trip to Florida, or perhaps it’s the return of semi-chilly weather earlier in April that has me digging the chance to , well, actually wear shorts now that it’s a bit warmer — regardless, that’s where we’re headed today. Just because you go with a more casual vibe (note the drawstring shorts below) doesn’t mean you have to look sloppy. That’s doubly true even if it rains or it’s breezy — you don’t want just any spring jacket. In the case of the below, we’re talking serious protection from the elements, and some neat heritage style thrown in the mix. Work in some new spring sneakers and an easygoing watch, and you’ll be all set no matter how hard the rain comes down. Sound good? Good. Want to see a different #OOTD? Head to The Style Guide’s Facebook page for a chat!

Casual vibes upgraded thanks to some high-quality brands & subtle style details.

Casual vibes upgraded thanks to some high-quality brands & subtle style details.

The Jacket: Taylor Stitch Beach Jacket in Navy, $128: Another standout from a brand that’s chock full of ’em, this piece is currently pre-funding, but the general idea remains the same — tough outerwear can look great and take you very far. You could also grab a classic JackThreads Mac Jacket and perhaps some light wash denim instead if you wanted something similar now.

The T-Shirt: Bridge and Burn Graphic Tee, $36: The tee keeps this outfit casual (so it’s probably more weekend-minded), but it’s part of some style ugprades we’ve talked about — the graphic is subtle and understated, and the fit is on-point.

The Shorts: JACHS NY Indigo Linen Shorts, $89: Another fantastic style upgrade from standard shorts, they’re easygoing yet not frumpy. If it’s a bit breezy or you want to dress this outfit up, sub in a chambray shirt & dark denim.

The Sneakers: The Hill-Side Standard Low-Tops in Natural Duck Canvas, $175: If you haven’t gotten around to checking out a pair of The Hill-Side sneakers, I’d recommend you do so. Sturdy, well-crafted and stylish!

The Socks: Mack Weldon No-Show Socks, $14.50: The same brand that makes your favorite merino T-shirt also makes some handy socks for that “ankles-out” look so common in the warmer months.

The Trunks: Mack Weldon 18-Hour Jersey Trunks, $22: Just as their socks are worth a look, this brand knows how to craft a great pair of underwear (no, really). Again, an investment that’s also a significant style upgrade from standard boxers.

The Watch: Timex Weekender Fairfield, $75: A downright simple watch for a downright excellent price, ideal for all kinds of casual wear.

The Sunglasses: Spine Optics Aviator Sunglasses, $88.99: As with the above Timex watch, sometimes, simple is better. These sunglasses are durable and remarkably flexible, and won’t upstage the rest of your look.

As with other seasonal spring style suggestions, be it how to dress for Sunday brunch or how to prep for a spring bar crawl, your gear should fit where you’re going. That is, if a T-shirt needs to be subbed out for a slim plaid shirt, that’s the move to make. But alongside that, choosing to upgrade your casual basics — like standard sneakers for a sturdier pair, or old boxers for new trunks — should also be top of mind. Wardrobe reinvention doesn’t have to be done all at once, but small steps can pave the way toward great style. Pick up that Taylor Stitch jacket for me while you’re at it, ehh?

Stay stylish,

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Online Shopping Picks: The 5 Best Men’s Watches to Buy Now

Editor’s note: To feast your eyes on all kinds of #menswear shopping picks, click over here.

Curious about what casual watch you need in your arsenal? Read on. The Stuhrling Aquadiver Manta Ray is pictured here. Vintage ballcap by Goorin Brothers. Striped chambray shirt by JACHS NY. Sneakers by Reef. Sunglasses by Tom Ford. Sweatshorts by Pistol Lake.

Curious about what casual watch you need in your arsenal? Read on. The Stuhrling Aquadiver Manta Ray is pictured here. Vintage ballcap by Goorin Brothers. Striped chambray shirt by JACHS NY. Sneakers by Reef. Sunglasses by Tom Ford. Sweatshorts by Pistol Lake.

Look down at your right wrist. Now, look down at your left wrist. Do you have a great watch on? Yes? No? Can’t tell? I’m here to help you sort that out today. When it comes to style upgrades, there’s no messing about here at The Style Guide. As a guy constantly on the hunt for a great watch, it’s an area that’s been a focus for me as of late — we even covered off on some more men’s watches on a budget last spring, so it’s high time to get after it again. And although it might not be the first thing you look to buy for yourself (whether you’ve owned a timepiece before or not), it can play a pretty crucial role in tying together an outfit. The right accessories just work that way. And while a casual watch might seem a bit out of place, we’re looking today for watches that you’d wear to, say, a relaxed spring bar crawl or a casual Sunday brunch, not to a boardroom meeting. Specifically, look for something Bond might wear in the Moroccan desert — you see where we’re headed with this? The below picks definitely reflect that spirit of adventure without the high price tag — casual in nature, ready for spring and summer (and beyond), and designed with a slightly more rugged feel in mind. If you think I missed any pieces, give me a holler on Twitter! Talk to you soon!

#1. Timex Waterbury — $100

A unique offering from a brand that does casual watches very well.

A unique offering from a brand that does casual watches very well.

Note that the original Timex Weekender could very well fill this top spot, too — it was a close call! But the brand so well-known for that style is doing something a little different with its Waterbury line. These watches blend rugged style, like that slightly aged leather strap, with a simple contrasting design on the dial and no real frills anywhere. It’s the perfect watch to grab when you want to mimic a leather dress watch without such a minimal look (like at that Sunday brunch). The price is definitely tough to beat no matter where else you look — it’ll take a lickin’ and keep on tickin’, to quote the brand.

#2. Daniel Wellington Classic Glasgow 40mm Silver Watch, $195

A style Bond would be proud to wear -- the merger of a dress watch and a sport-inspired strap.

A style Bond would be proud to wear — the merger of a dress watch and a sport-inspired strap.

For those who prefer a slightly more crisp watch merged with the sporty nature of a NATO strap, here’s your winner. Daniel Wellington has taken the ultra-minimal design and thin case of a dress watch for its Classic Glasgow  and done it up in a sharp silver color. The striped white-and-blue NATO strap is practically begging to be worn alongside a slim pocket tee and a great pair of summer shorts — even if it looks a tad too dressy at first, a watch this well-designed can work with any outfit (just be sure to keep it out of the water — it’s not built to go quite that far).

#3. Timex for J. Crew Vintage Army Field Watch — $98

Based on a decades-old archival design, this watch is worth the higher price tag compared to other Timex watches.

Based on a decades-old archival design, this watch is worth the higher price tag compared to other Timex watches.

J. Crew continues to knock it out of the park when it comes to partnering with renowned third-party brands, and this particular watch has surely ended up on many a style wish list over the years because of that. The Timex for J. Crew timepiece in question is based on a style from the Timex archives that dates back to the 1940s — talk about timeless. The olive strap is neutral enough to match with almost anything, and the simple case markings and smaller case diameter make this one subtle, stylish watch — to say it’s perfect for a backyard barbeque would be an understatement.

#4. KOMONO Winston Heritage Chambray — $99.95

Chambray on a watch strap? Can't go wrong.

Chambray on a watch strap? Can’t go wrong.

While chambray as a shirting or trouser fabric is versatile enough to rock year-round, it’s not often seen on watch straps. In this instance though, the KOMONO Winston Heritage would be a unique, eye-catching addition to your watch collection — it’s just different enough visually from a brown leather watch to make it worth your time (pun intended). The acid wash chambray strap is a neat finishing touch that would play nicely off inky selvedge denim and a navy crewneck, and it would also work alongside a slim short-sleeve henley and light wash jeans this spring. Casual in nature, ya dig?

#5. Stuhrling Original Aquadiver Manta Ray Watch — $48.40

Ultra-tough and ultra-dependable, this rubber-strap Stuhrling watch just works.

Ultra-tough and ultra-dependable, this rubber-strap Stuhrling watch just works.

By far the most casual and least expensive watch on this list, perhaps the Stuhrling Aquadiver is what you had in mind when thinking “casual watch.” A rubber strap watch is certainly the most rugged and dependable among this group, and it even performs just as a stainless steel dive watch might — that is, you can rock it in the water, on land and everywhere in between. It’s a heck of a steal for under $50, and my personal timepiece is still going strong after more than two years of use (read the full review here).

With a dearth of casual watches on the market, cutting any list off at five is tough. But brands that do dress watches well (like Daniel Wellington) also have the market cornered with more casual timepieces. MVMT Watches delivers options that certainly drift a bit louder in terms of style (like this all-black, rugged watch), but they could be a wise pickup if you’re a fan of the brand. If you fancy yourself a watch collector with some cash to burn, you could feasibly snag the same watch worn by James Bond in Spectre. Oh, man. On the slightly cheaper side of things, Shinola is even manufacturing super-rugged, sport-inspired watches that might be worth a look. If building up your watch collection is a goal of yours, start with the basics — like a brown leather dress watch — and then move into the more casual realm with picks that serve a twofold purpose. As for me? I think this list isn’t a bad place to start.

Until next time,

Stay stylish,



Style Suggestion: A Cozy Christmas

Editor’s note: For more Style Suggestions — including what to wear to that holiday party — swing through here.

Breaking news — Christmas is almost here! If you’re a big fan of the holidays, like me, and appreciate a festive atmosphere in the air and lights all around the cityscape (or your hometown), there’s really no better time to enjoy. But thankfully, the holiday also gives everyone a chance to rest, regroup and ideally, actually get home for some time off. Either way, Christmas and the events surrounding it don’t always have a set dress code — it could be a more casual evening of opening gifts with just the family, or a nice party with friends (hopefully, Ryan Gosling doesn’t drop by). So the style suggestion that follows definitely errs on the side of more casual, whether this is on Christmas Day itself or in the days leading up to. Bear in mind — this is just one suggestion to keep things from getting too sloppy, so mix-and-match (and buy) as you please! Note that we’ll cover a more dressed-up Christmas affair right here next week.

The Shirt: Tommy John Ringer Pocket Tee in Heather Grey — $34

This colorblocked pocket tee is a simple but effective upgrade from the pedestrian crewneck.

This colorblocked pocket tee is a simple but effective upgrade from the pedestrian crewneck.

So right off the bat, that price is a bit much more than most might pay for a T-shirt. BUT, bear with — Tommy John certainly seems to be the real deal as far as quality and comfort goes in the undershirt and T-shirt game. And its Ringer Pocket Tee (available in four colors) is soft, stylish and slim-fitting. Crucially, the color at the neck and pocket sets it apart just so slightly from a regular crewneck tee, even when that might be the cheaper option.  It’s these small style upgrades that can add a little thought to your look, and if comfort is part of the equation, it’s key to still look good. However, if wearing just a tee makes you wary, I’d reach for a great chambray shirt instead.

The Sweater: Old Navy Chunky Shawl-Collar Cardigan — $49.50 (When On-Sale)

A rich color and ribbed knit make this a solid house sweater for a cozy Christmas.

A rich color and ribbed knit make this a solid house sweater for a cozy Christmas.

Because it’s the heart of December, we’ll assume it could be a little bit chilly wherever you might be. That’s exactly the time to reach for a well-priced Old Navy cardigan. The burgundy color is a nice, on-trend nod to the season as a whole (although this cream JackThreads Shawl Cardigan could also be a neat, affordable pickup). But in this instance, the thick burgundy knit brings some nice contrast when paired alongside the lightweight T-shirt. As I’ve said time and again, a shawl-collar cardigan is a great, masculine style move that adds some rugged appeal to any outfit. Plus, who doesn’t love a cozy sweater? If it’s too warm out where you are, ditch it (if you’re lucky enough, that is!).

The Pants: JackThreads The Daily Jogger — $49.50 OR Classic Dark Denim

A dark color and trim cut help these wear less like sweats and more like jeans. Yes, you got that right.

A dark color and trim cut help these wear less like sweats and more like jeans. Yes, you got that right.

As we talked about above, Christmas can go one of two ways — more casual, or dressier. In this case, if you’ve got the option to go more laidback yet want to avoid wearing pajama pants, we’re going out on a limb to recommend a pair of tailored sweatpants in a dark color. JackThreads continues to get a lot of things right with its new menswear line, and stylish essentials at low prices like these are why. Again, if sweatpants still feel too casual, a solid pair of dark denim never fails (I’d recommend Mott & Bow, who makes slim jeans like its Hester model with a comfy hint of stretch). If sweats are too hot, reach for their laidback but just as comfy alternative — the well-crafted sweatshort (like these from my friends at Pistol Lake).

The Sneakers: GREATS Brand Royale Chukka — $152 (On-Sale)

Camel plus black in a chukka silhouette = dressier sneakers than the norm.

Camel plus black in a chukka silhouette = dressier sneakers than the norm.

If sneakers seem a silly option for the middle of winter (and they very well might be if there’s a ton of snow), I’d urge you to go with a reliable (but cheaper) desert boot instead. If, however, you’re able to rock some chukka sneakers from GREATS, you’ve found a style choice that fits right in with fall & winter yet feels more comfortable than a thicker boot (note that Reef’s Outhaul Lux Chukka does that, too). The Royale Chukka definitely checks all those boxes, and even more crucially, the camel color plus black sole is a combo that feels a little dressier than a plain pair of captoe sneakers. These sneakers can be worn through the rest of winter in the right weather, and into spring with some lightwash jeans, too — that’s the gift that keeps on giving.

The Watch: Timex Weekender 40mm — $46

A black leather strap and that simple Timex dial create the ideal happy medium for the rest of this outfit.

A black leather strap and that simple Timex dial create the ideal happy medium for the rest of this outfit.

Just as in this site’s Thanksgiving Style Suggestion, a Timex is the affordable watch pick once again. In this instance, Timex’s classic weekender dial keeps the watch more casual, but the black face and slip-thru black leather strap makes it ever so slightly put-together. Yet, it’ll still look right at home with this outfit in terms of color and styling potential — it’s just that simple and versatile. Lest we forget, this watch can be mixed and matched with other NATO straps — that’s like getting a new watch for about $10.

The Socks: Richer Poorer Herald Socks — $12

A small way to pump some pattern into an outfit -- for a low price.

A small way to pump some pattern into an outfit — for a low price.

Whereas the rest of this outfit mainly sticks to solid basics, these socks inject some life into the ensemble in a fun way. And assuming you’ll be kicking around without shoes on for a bit, clean, hole-free socks are a must (truly). Throw in a fun polka-dot pattern in a color that complements the rest of the outfit, and you’re set. The oatmeal color of these socks is also just different enough if you go with a heather-grey T-shirt (or even a blue chambray), and the navy dots complement the cardigan and the sneakers, too. Plus, Richer Poorer socks are springy and breathable — not a  heavy wool set.

While the above outfit might not work for everyone, here’s hoping you do get the chance to kick back in a more casual fashion this Christmas — and when that time comes, I hope you’ll keep some of these picks in mind (because who doesn’t love looking their best all the time?). Think I missed anything? Let me know your picks for the holiday season below!

Ben Sherman US

Style Suggestion: Memorial Day

Memorial Day really is one of the first significant outdoor occasions of the spring and summer for many around the country – after a long winter, summer’s imminent, and the holiday might bring with it some travel and time with friends and family. Ideally though, it involves getting outdoors for a little bit of everything — maybe a barbecque, a trip to the water or a little exploring. But what do you wear for such an occasion? Tweaking the standard outdoor get-up doesn’t take that much work — and you can support some quality brands in the process.

The Shirt: Buck Mason Navy Crew Slub Tee — $24

Small design touches make this a better option than a regular tank top or ratty old T-shirt.

Small design touches make this a better option than a regular tank top or ratty old T-shirt.

First seen not too long ago on this site’s roundup of the best T-shirts for spring and summer, this pick is much more than just a T-shirt. The deep navy color and slubby texture differentiate it from a plain old tee, and the rounded hem and slouchy collar are added design touches, too. The fact that it’s American-made doesn’t hurt, either. If the situations calls for a polo, you could always pick up a cheap yet well-designed option from this year’s Michael Bastian x Uniqlo collaboration or perhaps a nice short-sleeve buttondown from Ernest Alexander.

The Shorts: J. Crew Factory Stadium Short in Chambray — $29.50

Sporty elements like the elastic waistband mesh with an airy chambray fabric in these shorts.

Sporty elements like the elastic waistband mesh with an airy chambray fabric in these shorts.

Some might argue that these are just a shorter version of jogger pants – why add in something like a drawstring waistband to a pair of shorts? Well, when you’re out and about on Memorial Day, you might find yourself playing catch, grilling or taking a hike — the elastic waistband adds a casual and functional element to these chambray shorts, while the fabric and construction are a notch above athletic shorts (no belt needed, either). If you find they’re still too casual, you could grab a more refined pair from this list.

The Sneakers: GREATS Brand White Wilson Sneakers — $49

A durable captoe and the crisp white color make these the perfect high-low sneaker option.

A durable captoe and the crisp white color make these the perfect high-low sneaker option.

A full review of these sneakers can be found here  — but in short, they’re the ideal combination of excellent looks for a stellar price. They’re quite a bit cheaper than a pair of similar white kicks from the revamped Converse Jack Purcell line, they look more crisp than a pair of Chuck Taylor All-Stars (no pesky logo or side stripe on the sole), and they’re still functional enough to move around in — plus, at that price they can take a bit of a beating without too much worry. If you want a more no-frills option, you could always pick up a leather slip-on (the latest release from GREATS) or a beater pair of  canvas Vans sneakers.

The Socks: Richer Poorer Beginner No-Show 2-pack — $15

No-show socks that'll help your sneakers fit better and  last longer.

No-show socks that’ll help your sneakers fit better and last longer.

No-show socks are among those essentials for the warmer weather that can make quite a big difference — they prolong the life of your sneakers and help your kicks fit better while avoiding the foot funk that can come from going barefoot with shoes. The simple design options for Richer Poorer socks mean these are a better choice than no-show or low-cut athletic socks, too.

The Sunglasses: J. Crew Factory Tortoiseshell Sunglasses — $19.50

Mighty cheap but still stylish.

Mighty cheap but still stylish.

Some people are all about their sunglasses and really dig expensive pairs – if you’re not one of those people, or if you’re the type to lose them or sit on them throughout the summer, it doesn’t hurt to snag a pair or two of these cheap shades. You still get a unique frame shape, neat tortoiseshell pattern and the confidence of buying from J. Crew Factory — better than a drug store pair, right? You could always spring for a customizable pair of Ray-Ban’s New Wayfarers or an American classic, Randolph Engineering Aviators.

The Watch: Timex Weekender Slip-Thru Strap Watch — $40.45

A no-frills design that takes a licking and keeps on ticking.

A no-frills design that takes a licking and keeps on ticking.

Timex watches are renowned for the combo of price and durability they provide. The company doesn’t produce anything overly fancy, but its Weekender series works with plenty of NATO watch straps and provides a classic, clean design that’s not too casual or dressy. In this case, the red and blue stripes of the strap play off the blue in the shirt and the grey of the shorts, although a red floral NATO strap would also provide a fun pop of pattern and color. An efficient field watch would also work here.

With some slight tweaks, this same outfit template could work for nearly any warm-weather situation in your future — and either way, I hope your Memorial Day entails great times with friends and family … and maybe a cold beer or two.

What do you think of the above get-up?What will you be wearing (and doing!) for the long weekend?

Ernest Alexander
Nunn Bush