#OOTD: How to Dress for a Casual Winter Weekend

Alright folks, here we go with another take on the #OOTD. There comes a time in your life when duty calls — when you want to get out of the house to head to brunch, or grab a cocktail, or pick up some more coffee, or reload for that home proejct — and it’s just got to be done in spite of the weather. That’s why we’re here: To tell you how to dress for a casual winter weekend, helped along by plenty of seasonal style essentials. The right winter weekend #OOTD ties everything together with functionality and style in mind — so, for fighting windy weather and snowstorms, you’ll find a rugged waxed jacket to take on the elements. Other layers come in handy once you’ve bellied up to the bar and taken off said jacket — take, for instance, one of the best new flannel shirts (more on that one in a moment). And classics like slim dark blue jeans never fail — inside or outside, coffee date or a quick trip into town. All these picks are more crucial than you think, including Red Wing Heritage boots for dependability and durability on slippery streets. The goal here should be gear picks that look great and don’t miss a beat from day-to-night, so you’ll also find crucial layers like one of the best men’s henleys. Check out the full look below, and let me know in the comments if you think we (and by we, I mean me) hit our goal. Cheers!

You’ll be able to go just about anywhere this winter with these rugged gear picks.

Ready to brave the elements? As taxing as that might sound at the moment, I know I am — it all comes down to starting with the right layers, and then building from there. In this case, the right layers just so happen to include a rugged waxed jacket that’ll fight off winter’s worst pretty handily. Layering a Faherty Brand flannel shirt is the right way to go for both warmth and style, plus a bit of versatility — that’s the sort of shirt you can wear to a casual lunch or a trip to your favorite bar in equal measure. You could also argue that if you’re not wearing a Taylor Stitch henley as your base layer, you’re not doing it right this season — that’s debateable, but there’s an argument to be made for making a rugged henley part of your menswear rotation. Naturally, Mott and Bow denim never fails in terms of style points or dependability — the same could be said for those go-anywhere Red Wing Heritage boots, all the better to beat out winter snow. Your accessories are also going to seal the deal here, from one of the best winter hats to a tough everyday bag that’ll keep your gear safe and sound. Of course, no look is complete without a rugged casual watch — that’s the right way to finish off this look. Where will this ensemble take you? Let me know on Twitter.

The List: Shop the Best New Menswear Essentials — From Boots to Denim — Right Here

A new favorite winter layer is today’s featured pick.

Welcome back and thanks for joining us as we cover another all-new set of men’s style essentials for winter (and well beyond!) here at The Style Guide. Today’s focus remains on versatile, durable, tough gear that’s going to get you through winter (and perhaps Valentine’s Day) with style and functionality in mind. That’s where a piece like the Relwen Knit Jacquard Snap CPO is going to come in handy — part blazer replacement, part shirt, part jacket, it’s one of the best men’s winter outerwear pieces you can buy now. And you’ll find out all about it below. To shop for more winter style essentials, be sure to check out past editions of The List. Happy shopping!

Relwen Knit Jacquard Snap CPO — $238.98


Dependable and smartly designed to layer with ease.

A richly crafted, stylish shirt jacket that’s exclusive to Huckberry is tough to pass up, right? Particularly one that’s made with military heritage and bombproof (yes, bombproof) construction in mind. The Knit Jacquard Snap CPO from Relwen is perfect to wear with slim grey chinos, tough moc toe leather boots and your favorite henley, naturally.

SHOP: The Knit Jacquard Snap CPO from Relwen

Fourlaps Rush Jogger 2.0 — $88

A pair of tailored joggers that function nicely for work or play.

Whether you throw on these sweats to take on a winter weekend 5K or perhaps a more leisurely park stroll, the Fourlaps Rush Joggers (2.0 Edition) blend sporty style with a tailored fit. The French Terry fabric blend is soft and cozy, another plus this winter. And if you fancy wearing sweatpants for travel, it’s hard to go wrong with this cleanly designed pair.
Bespoke Post Agenda Box — $45 (When You Sign Up for Bespoke Post)

Classic, sharp office style and organization essentials.

The good folks at Bespoke Post say that you can tell a lot about a man by his workspace, and they’re absolutely right. From a handsome leather desk pad to a sharply designed calendar, the Bespoke Post Agenda Box has the office essentials you need to upgrade your work day.
Santa Rosa Tahoma Moccasins — $280

Hard-wearing moc boots that channel throwback style.

From slim sweatpants right back to rugged leather boots we go. The Santa Rosa Tahoma Moccasins are made with some serious attention to detail, a quality that harkens back to the brand’s West Coast founding in 1906 (yes, 1906!). Try wearing these stylish moc boots with slim faded denim and a classic crewneck sweatshirt.
Luminox Xcor Aerospace Pilot Professional Watch — $1,900

One heck of an advanced-yet-stylish timepiece.

Is this technologically advanced Luminox watch a major splurge? Yes. Do you need it unless you’ve got a very adventure or day job? Perhaps not. But if you do, it’ll surely come through.
Faherty Brand Overdyed Denim in Faded Grey — $178

A nice switch from dark blue denim.

A new arrival to the Faherty Brand site, these slim overdyed jeans are a unique way to switch things up from inky dark denim. As always with Faherty Brand, the fit and fabric are on-point.
Bluegrass Barrels Black Hoop Aging Barrel — $60

A neat way to upgrade your home bar.

A premium aging barrel might not be the first thing you think of when you think of essentials for your home bar, but it’s one of the coolest and most underrated components — right?
Topo Designs Daypack — $169

A rugged backpack that blends functionality and style.

The use of handsome Horween leather makes this Topo Designs backpack go from good to great — like, really great. In short, the Topo Designs Daypack is the new backpack you need now, fit for winter travel or a casual weekend outing.
Far Afield Tanner Ribbed Knit — $150

A standout sweater from a brand that knows its heritage.

There are certain classic men’s sweaters that really embody winter layering at its finest. The rugged, throwback-inspired Far Afield Tanner Ribbed Knit is one such sweater.
Taylor Stitch Slim Chinos in Organic Ash — $98
Taylor Stitch review

A pair of classic chinos in a unique color.

Part of the excellent Essentials Collection from Taylor Stitch (year-round staples from a trusted brand), these Taylor Stitch Slim Chinos are a winter standout. Wear them with the Far Afield Tanner Ribbed Knit — plus brown leather boots — for casual office style.
Rhone Apparel Space Dye Henley — $78

An innovative henley that’s perfect for throwing on as a durable base layer.

Are you sensing a theme here? From the Taylor Stitch Slim Chinos to the Far Afield Tanner Ribbed Knit, the focus is on durable winter layering — a la this stylish henley from Rhone.
Mission Belt Full-Grain Italian Leather Belt — $74.95
Mission Belt

A new way to design and wear a belt, with a great cause in mind.

As seen on Shark Tank, Mission Belt really is like no other belt company out there, from the fact that its belts have no holes (they use a neat slide-and-clip mechanism instead!) to the fact that a dollar from every belt goes toward micro-loans to help entrepreneurs in developing countries. After testing it recently, I love the Cognac Italian Leather Belt as seen above.
Ash & Fir Upstate Candle Trio — $54

Three candle choices that mimic the scent and feel of lovely upstate New York.

Especially as we roll through winter, don’t overlook the importance of stocking up on the best candles for your home or apartment. You get three nicely scented candles here from Ash & Fir, luckily.
Outerknown Local Straight Denim — $128

A pair of jeans that look great and help the environment? That’s more than worthy of a purchase.

We’ll close out today’s edition of The List by looking at stylish men’s denim that’s also made with a mission in mind — Outerknown’s Local Straight Denim is sustainably made, and the handsome Faded Indigo wash is a new way to wear your favorite denim that’s much better for the environment. Plus, this stylish pair of jeans features a classic (not too skinny or baggy) fit.
So, from slim jogger sweatpants to an incredible technical watch from Luminox, we really covered something for everyone today, did we not? Which pick was your favorite? As we talked about at the top of the post, I can’t get enough of the Knit Jacquard Snap CPO from Relwen. Let me know how you feel about the rest of these picks on Twitter. Cheers!

#OOTD: Layering Up in Style This Winter

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.

OK, so first of all — it’s Valentine’s Day! I hope you’re spending the day just as you’d like, and in style. To that end —  if you’re looking to shore up or switch up your casual winter style  after a few months of bone-chilling cold, this week’s #OOTD will sort that out nicely for you. We talked last month about how to wear a turtleneck this winter, but we’re going a bit more accessible and a bit more versatile today — as you’ll see below. It’s taking pieces that you might already have in your wardrobe, or pieces that you might be coveting — ahem, the Taylor Stitch Maritime Submariner Jacket — and putting in all together in a look that you can wear any day of the week. So, Sunday brunch? Check. Heck, Saturday brunch? You got it. And a weekend coffee date or a business casual day at the office? Absolutely. For more daily style inspiration, follow your Style Guide author on Instagram. Join us later this week for our regularly scheduled #menswear programming, too. Happy shopping!

Taylor Stitch

Taking classic pieces and upgrading the fabrics and fits.

The Jacket: Taylor Stitch Maritime Submariner Jacket, $248 — Ahh, yes. The warm, comfortable, slim-fitting and versatile Taylor Stitch Maritime Submariner Jacket. How could you not love it? Right? Right.

The Sweater: Bonobos Merino V-Neck Sweater, $58 — If you’re going to wear something more simple in form — like a V-neck sweater — you might as well make yours a high-quality, well-fitting piece in a rich winter color. Wondering how it should fit?  Read my recent Effortless Gent piece on how to find the perfect sweater (nudge, nudge).

The Oxford: JackThreads The Oxford Shirt, $39 — Is there a more classic combination for versatile, casual style than a V-neck sweater and an Oxford? Not quite — especially when it’s a great deal from the folks at JackThreads.

The Denim: Buck Mason Lou Slim Fit Jean, $175 — If you haven’t checked out Buck Mason, I’d advise you do so — from the brand’s classic short-sleeve chambray shirts to slim denim like this pair (faded just right), it’s tough gear for the modern man.

The Boots: Astorflex Bitflex Chelsea Boots, $180 — As sold by everyone’s favorite E-commerce retailer — that’s Huckberry, y’all — Astorflex makes essential, sustainable and stylish footwear. Yes, the Bitflex Chelsea Boots are a winning footwear choice.

The Belt: Abercrombie & Fitch Leather Belt, $44 — Sometimes, your accessories help define a casual ensemble. In this instance, a textured belt tones things down in comparison to a slim dress belt.

The Socks:  American Trench Pima Cotton Houndstooth Socks, $16.98 — If you’re going to fill your sock drawer with only the best, might as well make your picks from American Trench — the brand makes beautiful, comfortable socks.

The Watch:  Tanner Goods Martenero Ace Automatic Watch, $549.98 — Just as a textured leather belt places this outfit in casual territory, so too does a rugged, handsome and eye-catching watch with tough Tanner Gods leather.  Truly, the Ace Automatic Watch is expertly designed and made to stand up to anything.

With versatility and great comfort & fit in mind, dressing in casual style can be easy and hey, fun. And if you’ve been looking for ways to switch up your style this winter, a great V-neck and Oxford is one way to go. These are pieces you might already have, but you can amp things up with something like the handsome, rugged Maritime Submariner Jacket and slick footwear like the Astorflex Bitflex Chelsea Boots. Oh, and if adding to your watch collection is a priority in terms of your 2017 style resolutions, there’s no better place to start than the very investment-worthy Ace Automatic Watch. If you have any questions or suggestions on this outfit, drop ’em in the comments or hit me up on Twitter. Talk to you soon, and thank you for reading!


Frank & Oak

Style Suggestion: The Holiday Party

How do you take your martini, Mr. Bond? (Just don't hit 'em too hard at your holiday party).

How do you take your martini, Mr. Bond? (Just don’t hit ’em too hard at your holiday party).

With the arrival of December comes an occasion some of us definitely look forward to, and others tend to dread – the holiday party.  Depending on where you work or where you’re invited, it might be lots of fun… or decidedly not-so-fun. The same goes for holiday parties with family and friends – although hopefully those are enjoyable. And regardless of the situation, it behooves you (yes, I just used that word) to clean up appropriately. Plus, dressing up smartly can be quite fun – especially when you change up just a few things from your co-workers or friends (like fit and color/texture combos) and end up looking like a  million bucks (or at least deserving of that bonus). What follows is a suggestion that can go either CEO-level dressy for a fancy holiday party, or a bit toned-down for slamming some nog at a friend’s house (people do that, right?).  Stand by for further style suggestions later this month covering both a laidback Christmas and a more dressed-up Yuletide celebration. Enjoy, and happy holidays!
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The Overcoat: Combatant Gentleman Navy Wool Overcoat — $120

A versatile navy color, a slim fit and a great price make for a terrific top layer.

A versatile navy color, a slim fit and a great price make for a terrific top layer.

Before we get into what to wear for the rest of your night, let’s assume it’ll be cold before you get into that party — and let’s assume you’re in need of an outerwear revamp. There’s no denying the style power and versatility of a great topcoat, and this navy wool overcoat from Combatant Gentleman fits the bill perfectly. Its price is more than solid, and for a new introduction to the brand, it would seem that the quality should be on-point from past experience. The fit looks to be trim yet workable over a suit, and the soft Italian wool should also be workable for that pricepoint. The navy color is going to work with all kinds of outfits outside of this particular occasion, as well.

The Suit Or Sweater: Combatant Gentleman Charcoal Birdseye Slim Fit Suit — $200 OR Frank & Oak Merino Cardigan in Bitter Chocolate — $70 And J. Crew Factory Thompson Slim Voyager Suit Pants — $84

Two options, one dressy and one more casual -- but both affordable.

Two options, one dressy and one more casual — but both affordable.

So Combatant Gentleman is the pick for our suiting option as well, but not just for kicks. The brand has made its mark in the affordable tailoring realm, offering up solid picks for more-than-agreeable prices. Its blazers, while not 100% perfect, are also an extremely great value for the price. So picking up one of its charcoal suits can knock out two birds with one stone – if you’re in need of a first-time suit on a budget, or if you want to refresh your suiting game for not a lot of dough. This birdseye suit is a nice visual departure from a flat charcoal color, too. If the occasion doesn’t call for a suit, you can swap in a crisp, slim Frank & Oak cardigan (much sleeker than a thicker shawl number). That can then be paired with some navy wool trousers and accomplish the same goal. Of course, dark denim can be swapped in with your cardigan for an even more toned-down look.

The Shirt: Standard Shirt White Dress Shirt — $59

Take your pick of two collar styles, both for a tremendous price from Standard Shirt.

Take your pick of two collar styles, both for a tremendous price from Standard Shirt.

While it’s worth looking at a site like EXPRESS for its shirt deals, there’s not a shirt that offers a price-quality ratio quite like Standard Shirt; that makes sense given that two styles of white dress shirts are all the company does. And they combine that quality with smaller touches (like a wider, suit-ready collar) in an inexpensive package. I threw on the brand’s spread collar shirt for a rather sweltering Michigan wedding and was also pleasantly surprised with its breathability. The crisp white shirt is definitely going to be a great anchor for either the suit or cardigan any way you look at it.

The Tie: The Tie Bar Midnight Navy Grenafaux Tie — $19

A tie with some visual interest to complement the birdseye weave of the suit.

A tie with some visual interest at a low price.

If you need to ditch the tie in favor of just that slim cardigan or tailored charcoal suit over a crisp shirt, that’s the way to go. But if you do still need that tie, The Tie Bar, as always, has you covered. While a navy knit tie could also be a good, versatile buy in this case, a grenafaux tie brings that same amount of texture and visual interest while looking a bit more suit-ready. And in this case, the texture of the tie will bring a bit more punch than a standard silk number, allowing it to stand up to the birdseye suit nicely.

The Pocket Square: General Knot & Co. 1940s Crimson Duck Pocket Square — $38 OR The Tie Bar Light Champagne Herringbone Pocket Square — $10

Take your pick of either vintage fabric and a higher price, or an old standby in a nice fabric.

Take your pick of either vintage fabric and a higher price, or an old standby in a nice fabric.

So we have two pocket square options here – one that’s flashy and conversation-worthy, made from vintage fabric, and one that’s still conversation-worthy, but mainly for the punch of pattern and color it brings. When your suit and tie both have some texture, throwing in another dash in a contrasting color still works, mainly because of that color difference. Either would add a bit something extra to your suit that a solid white pocket square might not (although that works with this outfit, too). While the price for the General Knot square is a bit of a splurge, keep in mind that if you go cardigan-only, you save that cash.

The Shoes:  Johnston & Murphy McGavock Wingtip Boot — $250

A dressy wingtip boot with seasonal fabric design touches to stand up to the chilly weather.

A dressy wingtip boot with seasonal fabric design touches to stand up to the chilly weather.

Johnston & Murphy can sometimes be a bit overlooked what with a company like Jack Erwin competing right in its wheelhouse, but the brand delivers on seasonal numbers, like these mixed-media boots. They’re the perfect middle ground for stomping through some snow or rain to get into that party, yet they still look crisp, slim and appropriate for tailored wear. There’s a touch of brown in there on the sole, but that won’t look too out of place next to the charcoal suit. If funding is tight, JC Penney’s classic Stafford Wingtip is going for a right steal now. Either way, black shoes can look especially sleek this time of year (and if SPECTRE is any indication, black shoes are going to be the way to go for the months ahead).

The  Belt: EXPRESS 2-in-1 Reversible Buckle Leather Belt in Black — $39.90

Two for the price of one, with a crisp look to boot.

Two for the price of one, with a crisp look to boot.

EXPRESS’ quality might sometimes be suspect, but when you need a belt (or in this case, two belts) at a decent price in a pinch, a reversible option never hurts. They do all kinds of belts, but this is a sharp, sleek pickup that’ll go well with those crisp black shoes and the dialed-in black watch (more on that below). You can always go beltless if you find that’s more sleek, however.

The Watch: KOMONO Winston Regal in Black — $99.95

Super-crisp style for under $100.

Super-crisp style for under $100.

KOMONO’s at it again – this brand flies under the radar occasionally, but its dressier watches are just as solid a value as its more casual, seasonally focused timepieces (like the Winston Herringbone timepiece I reviewed earlier this fall). The Winston Regal in Black is super-sharp, and the thin case and no-nonsense dial fall right in line with the sharp pieces in the rest of this ensemble, from the black boots to the crisp white shirt and black belt. And at under $100, it’s an excellent steal on a budget.

The Socks: American Trench Dress Rib Sock in Cloud Grey — $14.50

High-quality socks that'll be worth more than the price tag.

High-quality socks that’ll be worth more than the price tag.

Whereas we’ve dialed it back with the suit and watch, these socks tip the scales more in terms of price. American Trench is a Style Guide favorite (check out more on its socks here), and there really isn’t a brand doing made-in-America socks as well as they do. So in this instance, it makes sense to splurge on some high-quality dress socks that can stand up to repeated wear with a workhorse charcoal suit; while socks with a pop of color are an option too, you might be pleasantly surprised at how sharp a sock looks when matched with a trouser (especially in a clean charcoal-on-charcoal combo).

While it can be a bit off-putting to see so many dark colors in an outfit, from the suit to the pocket square to the shoes, belt and watch,  it can be refreshing to go sleek, simple and yet still put-together. Plus, other cold-weather occasions leave plenty of time for working in colors, and each of the above pieces can be mixed and matched into those outfits as well. So go sharp this holiday season and see where it takes you. Once again, enjoy and let me know your holiday outfit picks below.

What do you think of the above ensemble? Will you be going dressy or casual this year at your holiday party?

Ben Sherman US