#OOTD: Your New Favorite Way to Dress for a Breezy Spring Day

You might have a picture-perfect idea of the type of day for which today’s #OOTD might fit. It’s a little bit brisk, but not too much so … it’s sunny … but it might rain later … and you’re looking forward to indulging in some early spring sunshine and perhaps, a classic spring beer. So, what are you wearing?  Well, let’s start things out with a stylish rain jacket that just so happens to be weather-ready, then let’s add a slim cashmere sweater, a classic Taylor Stitch shirt, and travel-friendly pants. How does that sound? Not bad, right? The key with dressing for a breezy spring day involves recognizing that you’ll need to be prepared for anything — brunch could lead to a farmer’s market trip, which could lead to patio beers. Or, heck, you might just be wondering what to wear to the office this spring. At any rate, I feel confident the below gear picks will suffice. That goes for the durable waterproof boots we’re recommending, along with the classic field watch on your wrist. I think you’ll be that much more ready for the season when you read all about the rest of today’s men’s style essentials below. Now, who’s ready for a Founders Solid Gold?

What do you get when you blend a lightweight, durable jacket with spring style essentials? This #OOTD, of course.

It’s not every day you get to put together an ensemble full of men’s style essentials to take you through plenty of different style situations — just like the picks shown above. It all comes together thanks to the functional rain jacket from Proof, perfect for taking on spring showers or simply serving as another layer when the temperature dips unexpectedly. From there, it only gets better: A slim cashmere crewneck is a lightweight, comfortable layer atop the Taylor Stitch Jack Shirt, and if it gets too hot out? Simply ditch the sweater. The Proof Rover Pants are also a winning essential, made to move with you no matter where your day takes you. The same can certainly be said for the dependable, rugged leather boots from Tricker’s shown here — pair them up with a set of Topo Designs socks for all-day comfort. When it comes to your everyday carry, you can never go wrong with a tough field watch — ideal for the office or your favorite brewpub. And what to bring along to keep all your gear safe? That’s easy. Simply reach for what could be the the perfect spring travel bag from WP Standard. There we go! What’s your take on this early spring #menswear ensemble? Let me know via Twitter. Cheers!

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#OOTD: A New Way to Wear Your Henley this Spring

So, you think you’ve got your transitional spring style all figured out, ehh? Maybe you’ve even picked up a rugged henley for the new season from a trusted brand like Flint and Tinder. But how to wear it? That’s why we’re here today, folks. Something as classic as a slub waffle henley can be easily overlooked when it comes to your rotation of spring style essentials — especially if it’s subtly stylish and doesn’t call attention to itself. That’s why we’re amping things up today with a new way to wear your henley for spring. Make no mistake, this isn’t an ensemble you would wear if you want tips on how to dress for the office — this outfit is perfectly rugged and ready for a spring weekend. Again, it all starts with a versatile henley and builds from there, including unique layering pieces like an indigo denim trucker jacket from Levi’s, tough workwear pants and naturally, rugged leather boots. I think you’ll find the overall effect is pleasing and unique, without straying too far into fashion-forward territory. So, let’s dive into the rest below, shall we?

The right way to pair up a classic henley with other men’s style essentials.

When you start out your #OOTD with a men’s style essential as reliable and classic as the timeless men’s henley, you’re guaranteed to like the results (at least, that’s what I think). The henley really is a go-anywhere piece. All that being said, we’re not exactly reinventing the wheel here … and there’s nothing wrong with that. Teaming up your henley with a classic trucker jacket from Levi’s is but another way to freshen things up. The same can be said for the choice to throw on rugged workwear pants instead of slim tan chinos or charcoal five-pocket pants (although both would work well here, too). And on the footwear front, I’m always a proponent of rugged leather boots — the boots pictured above make this ensemble one that’s fit for a weekend burger bar outing or a casual Sunday brunch (or an early morning coffee run, or even a concert … you get the picture). What’s more, reaching for a stylish leather watch from Carpenter Watches upgrades this outfit even further, taking it from, well, just good … to great.

Accessories that get the job done, from the Topo Designs Town Socks to the durable Bexar Goods weekender bag, are critical in any outfit, much less a versatile pairing like this one. Top it all off and look your best with men’s grooming essentials from Bespoke Post, then call it a day. Or, actually, don’t. You’ve got plenty of places to go wearing your new favorite henley

#OOTD: How to Dress for an Outdoor Adventure During Early Spring

The fun part about the slowly changing seasons has to be the potential for renewed energy in what you’re wearing — and what you’re able to do outside. Been feeling cooped up inside all winter? Today’s #OOTD on how to dress for spring (or early spring, at least) is downright essential and just plain fun when it comes to outfitting you in the men’s style essentials you need. It all kicks off with the need to layer up the right way, whether your idea of a spring adventure means a visit to your local park or a day hike upstate. For that, we’re turning toward the Topo Designs Field Shirt and some essential outdoor pieces (like the Topo Designs Field Pants, as luck would have it). A rugged parka made from waxed canvas helps keep you dry in the elements, while we’re accenting the rest of this outfit with durable leather boots, a field-ready watch and plenty (believe me, plenty) more standout picks. It’s just a matter of mixing and matching them for the occasion — and again, the slow transition into a new season brings with it a host of opportunities to dress for exploration. A new coffee shop?A new outdoor art exhibit? Add in a few craft brews, suit up with the below spring style essentials, then call it good.

A mix of rugged, outdoor-ready pieces and versatile style for spring — get out there.

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  • The Parka: Flint and Tinder Waxed Ridge Parka, $398 — A rugged, tough parka that’s going to stand up to rainy, blustery weather and keep you warm — well-done as always, Flint and Tinder.
  • The Shirt: Topo Designs Field Shirt, $89 — If you’re going to take on a spring adventure (be it a day hike or a casual park stroll), you might as well dress the part with Topo Designs — the rich Plaid pattern is cool without being too outdoors-y, while the organic cotton features a soft brushed interior for easy layering.
  • The Pants: Topo Designs Field Pants, $89 — More gear from Topo Designs? Indeed. The Field Pants feature midweight organic cotton twill for durability, plus a classic straight fit for ease of movement. Wear them to your favorite brewery after.
  • The Rugged Boots: White’s Boots MP-M1 Boots, $600 — These rugged leather boots can work out in the field or in the city, heading out on a short hike or heading out for an Old Fashioned — easy as that.
  • The Adventure-Ready Watch: Jack Mason Field Camp Watch, $175 — You need a stylish field watch that can handle anything your spring adventure throws your way, and Jack Mason has come through with one that’s understated and functional.
  • The Socks: Proof 72-Hour Merino Crew Socks, $32 — How hard can it be to find comfortable, stylish socks? Quite hard — these Proof Merino Socks solve that problem for all of your spring excursions, though.
  • The Durable Bag: Bexar Goods Co. Waxed Canvas LAND Duffel, $395 — Maybe your spring adventure involves a picnic or hauling a ton of gear, or some rough-and-tumble chores in the yard. Either way, the Bexar Goods Co. Waxed Duffel is ready for all of it. Talk about a durable everyday bag, am I right?
  • The Hat: Corridor Natural Vege Suede Cap, $45 — In the event of too much rain or too much sun, this American-made cap from Corridor again marries function and style nicely.

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It truly wouldn’t be the start of a transition to the new season without rugged, go-anywhere layering pieces like the Topo Designs Field Shirt,  would it? The same can be said for the rugged, dependable Topo Designs Field Pants — and those two pieces are stellar building blocks for the rest of this ensemble. You’re getting a dose of weather-ready style & versatility via a rugged, tough parka from Flint and Tinder, too — versatility in spades, my friend. Heck, it’s that kind of easy wearability that would allow this outfit to work in a variety of places, from an art gallery visit to a hike to an early spring rooftop happy hour. Complementary items like the Jack Mason Field Camp Watch drive that point home nicely, too. What’s more, rugged leather boots give you crucial performance you’re going to need during all sorts of spring excursions, from your local park to that new distillery in town. And although they can be hard to find at times, comfortable, stylish socks pull the whole outfit together, allowing you to stay on your feet for hours at a time. Lastly, we’d be remiss not to mention the importance (in matters of both functionality and style) of an American-made cap from Corridor. The whole ensemble also gets a nice, functional lift from the Bexar Goods Co. Waxed Duffel, which is well-suited for travel or for everyday adventures. The only question now is where exactly this #OOTD is going to take you.

#OOTD: Refresh Your Classic Oxford Shirt This Way for Winter, Right Now

There are only so many ways you can wear your classic Oxford shirt this winter, right? And if you feel like you’ve exhausted all of them, then you’re in luck — today’s new #OOTD is here to save the day with a completely revamped take on this timeless menswear essential. The Oxford shirt has been a men’s style go-to for decades because it A) Looks great on every guy and B) Lends itself to both classic styling (think tan chinos and leather loafers in the spring) or something a bit more fashion-forward (underneath a black moto jacket with slim grey jeans right now). It’s also ready-made for layering, what with the visually interesting buttondown collar and a tailored fit. In short, it’s asking to be worn a multitude of different ways. And in this instance, you get the best of, well, everything via the Taylor Stitch Jack Shirt that we’re showcasing below. It’s done up in cool-as-can-be color, all the better for layering underneath an unexpected workwear jacket — just the right way to switch up your style this winter. After all, we’re through February and likely still have some snowy, rainy weather ahead (Spoiler: The Blundstone boots shown below are going to come in handy). However, you needn’t fully abandon your favorite classic pieces, seeing as this stylish Oxford shirt will still work quite nicely with slim chinos as detailed below. How does it all come together? Well, you’ll have to read the rest of this #OOTD to find out. Cheers!

Mixing an Oxford shirt with some classic workwear essentials, including trusty Blundstone boots.

  • The Oxford Shirt: Taylor Stitch Jack Shirt in Army Everyday Oxford, $98 — The best way to shake up your classic Oxford shirt? Reaching for one from Taylor Stitch in a unique color.
  • The Jacket: Flint and Tinder Mill Jacket, $98 — Yet another way to change up how you’re wearing your Oxford shirt this winter? Layering it up with a tough workwear jacket from Flint and Tinder, rather than a blazer (consider this a Casual Friday style move).
  • The Classic Chinos: Taylor Stitch Democratic Chinos in Organic Ash, $98 — The folks at Taylor Stitch get the nod again here, thanks in part to the quality behind these slim grey chinos — a nice change of pace from expertly faded denim.
  • The Boots: Blundstone Super 550 Boots, $185 — We’re all about changing things up, and the timeless Blundstone boots shown here channel both functional and fashionable style.
  • The Watch: Laco Paderborn Original Pilot Watch, $1,190 — There’s a very good chance this investment-worthy leather watch might be sold out by the time you read this, but if not … it’s the perfect complement to this #OOTD.
  • The Socks: Proof 72-Hour Merino Crew Socks, $32 — Sometimes, minimally designed socks with travel-ready technology are a must — Proof has you covered.
  • The Belt: WP Standard Officer’s Belt in Natural, $72 — A leather belt that gets better with age is an easy style move — no need to overthink it here.
  • The Stylish Scarf: American Trench Thermal Knit Cotton Scarf, $48 — Last but certainly not least, we’ll close out today’s recommendation with a stylish cotton scarf from American Trench.

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Hopefully, this ensemble got you thinking about a new and slightly refreshed way to wear your classic Oxford shirt. Again, it’s never a bad thing to rock a versatile shirt that you can layer up or dress down. When you take one with a cool color from Taylor Stitch and pair it up with a tough workwear jacket from Flint and Tinder, you’re already off to a great start. To put it lightly, you’ve got the makings of an ensemble made to head to your favorite brewery or stand out subtly at the office. Taylor Stitch is also a wise bet on your bottom half, as the slim grey chinos we’ve shown here just so happen to be a solid change of pace from classic dark denim. That same blend of upgraded style and classic functionality shines through on the footwear front, too — witness the iconic Blundstone Super 550 Boots you’ll be rocking. As always seems to be the case when it comes to these outfits, you can’t slip up on the accessories front … no sir, not with your socks (go with the Proof 72-Hour Crew Socks), nor your heritage-quality leather watch (from Laco). And since it’s still winter, you assuredly need to end things on a high note with a stylish cotton scarf from American Trench — it really is all covered here. The choice of where to take this outfit is now up to you.

#OOTD: How to Dress Down a Blazer This Winter

We’ve talked in the past here on The Style Guide about how to dress for the office, but we’re now taking that a step further today — how to dress down your blazer the right way. The move here involves dressing it down for a nice blend of workwear-inspired, ruggedly casual office style. It’s a tricky balance to get right, but I think you’ll find the below #OOTD gets the job done just fine (pun intended). The trick comes in the blazer you pick, and the supporting cast with which you surround yourself. In this case, the blazer in question is the unstructured, laidback-yet-polished Outerknown Ambassador Blazer — but more on that in a second.

In other matters, the rest of these men’s style essentials might look more like pieces you wear on the weekend: Consider a rugged Taylor Stitch henley and the durable-as-heck Flint and Tinder Mill Pants to now be stylish and essential enough to wear to the office. The key, again, comes with blending it all together in a way that’s polished and cool — not stuffy. So, you’ll also find a stylish leather watch and grooming essentials from Duke Cannon in the mix. It can be a bit uncomfortable at first to mix and match pieces that you normally feel might not work together, but when you put your mind to it … it all falls into place. See for yourself below, then check out my #OOTD rotation over on Instagram.

Can you dress down a blazer? Yes, with this #OOTD … you sure can.

  • The Blazer: Outerknown Ambassador Blazer, $325 — When wearing a blazer more casually (like with a stylish henley), reach for one that’s unstructured and easygoing — Outerknown has just the ticket. (While we’re at it, head here to get a discount on Outerknown).
  • The Henley: Taylor Stitch Heavy Bag Henley in Natural, $68 — If ever there was a henley to wear with a blazer, it’d be this rugged Taylor Stitch henley. Right?
  • The Pants: Flint and Tinder Mill Pants, $98 — Mixing workwear with more dressy style staples can be a bit of a daring move, but the rugged Flint and Tinder Mill Pants balance out the two nicely.
  • The Jacket: Taylor Stitch Winslow Parka, $238.98 — You’re still going to need one of the best men’s winter jackets for a little while longer — Taylor Stitch strikes again here, helping you get to the office and stay dry while doing it.
  • The Boots: Allen Edmonds Normandy Captoe Boots, $295 — Rugged leather lace-up boots are the go-to move here, particularly as you fight the elements in business casual style.
  • The Stylish Leather Watch: Martenero Ace Watch, $595 — This handsome leather watch is bold enough for the weekend & subtly stylish enough for the office.
  • The Grooming Essential: Duke Cannon Bourbon Solid Cologne, $25 — Try something new on for size — this refined cologne from Duke Cannon is truly like no other, and that’s why I love it.
  • The Everyday Carry Essential: This Is Ground Mod 5 Organizer, $385 — The right way to organize your daily work must-haves? This Is Ground, of course. Stylish AND sleek.

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So, we’re calling this meeting to a close today in terms of how to dress down your blazer — did this #OOTD get you thinking outside of the box a little bit? Again, it all comes down to making sure your blazer (in this case, the Outerknown Ambassador Blazer) is laidback and stylish enough to wear with pieces like a rugged Taylor Stitch henley and of course, the workwear-inspired Flint and Tinder Mill Pants. You get more assistance at bridging the gap between the rugged and the office-ready with the suitably tough-yet-classic Allen Edmonds Normandy Captoe Boots (a personal favorite as seen on GearMoose!). The other accessories do the heavy lifting here, too. That includes the exceptional Martenero Ace Watch (possibly the best leather watch to buy now), plus the essential Duke Cannon Solid Cologne. Both of those bring this ensemble right to the office. And for when the weather gets to be too rough? The durable Taylor Stitch Winslow Parka helps you stay dry in style. Every single base is covered, from what to wear on your commute to what to wear at the office — casually, of course.  Again, check out my Instagram to see how I’m dressing for the office on the daily. Thanks for reading!


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#OOTD: The Best Way to Wear a Classic Henley for Winter (And Beyond)

If you keep up with the digital pages of your favorite menswear blog (this one!), then you know that we positively love recommending a stylish henley for many a situation — and this crucial piece of menswear is perhaps no more important than during the winter months. The right henley to buy now can in fact be used as a crucial base layer — particularly the stylish indigo henley from Faherty Brand that forms the foundation of this #OOTD. It’s the perfect piece to complement the other gear picks on display here — taken in total, this is a rugged, causal, warm ensemble that I could see working everywhere from a laidback weekend bar outing to a snowy winter hike. Again, it all starts with a great henley, that classic men’s style staple that started as a sporting shirt and has now evolved into the shirt that every guy needs (arguably). So, why does this entire outfit stand on its own? You’ll see why in just a second, but know that we’re teaming up our rugged henley with a classic flannel shirt, durable work pants and a pair of the best men’s boots for winter. It’s all topped off with — naturally — a seriously warm sherpa trucker jacket from Flint and Tinder. Now, let’s unveil the ensemble, shall we? To see how I’m styling a henley this winter, head to my Instagram.

An absolutely unstoppable winter style combo, featuring a rugged henley (of course).

OK, folks — what do we think of the choices for this rugged, casual, exceptionally timeless winter look? To me, the base layer of a stylish henley is what makes it all go — especially one from Faherty Brand, guaranteed to be comfortable and easy to layer. That’s all the better when you consider the stylish flannel shirt we’re wearing atop it, right? And things only get warmer and better-looking from there: The Flint and Tinder Type 3 Sherpa-Lined Jacket really is as good as it gets. It’s the type of jacket that could take you on a brewery tour or through a museum trip, then out to a casual gastropub — the same can be said of the surprisingly versatile Union Work Pants from Iron & Resin.  The entire combo is elevated even further thanks to the tremendous Thorogood Beloit Boots (easily the best leather boots for the season). And your accessories will add some sheen to this outfit if you focus on picking up arguably the perfect casual watch — one that’s going to stand up to the challenge of winter weather and go-anywhere style. You could certainly say the same thing about your American Trench socks, which add another element of comfort and all-day performance. Again, trekking from a gallery to a brewery to drinks has never been so easy. Last but certainly not least, it really will pay off to put on a stylish beanie cap as temperatures continue to drop. Now, with all of that being said … where will this outfit take you? Let me know via The Style Guide Facebook page.

#OOTD: How to Dress for Valentine’s Day This Year

So, Valentine’s Day is coming up. Whether you’re married or in a relationship (an old one or particularly, a new one!) or still looking for love, the question might be on your mind: “What the heck am I going to wear?” Based on your plans (Dinner? Drinks? Both!?), you might be faced with a dilemma. But I think the below #OOTD checks all the right boxes, no matter what. First up, stick with a classic winter blazer, and then layer up accordingly — in this case, that means a cozy, tailored flannel shirt from Faherty Brand, slim navy chinos and rugged leather boots from my pals at Huckberry. It’s truly foolproof.

Granted, we’re not going full-on tuxedo here, nor are we recommending you wear one of the best flannel suits for a night out, but it’s still a sharp look that can work for a refined dinner-and-a-show outing, plus a nightcap. The key with dressing for Valentine’s Day comes in staying true to yourself — seriously. If you and your partner keep things low-key and make a nice dinner at home, leave the Grayers sportcoat behind. Heck, if you feel like wearing that same blazer out to a solo cocktail at your favorite bar, sure — go for it! The same building blocks are going to carry you through, from crucial outerwear like a tailored topcoat to accessories like a slim leather dress watch. We’ll top things off with a great Valentine’s Day gift, too. It’s all below, and I hope these picks lead to an enjoyable (if Hallmark-led) holiday — no matter what you do!

A crisp blazer, a sharp topcoat and stylish leather boots make for a winning Valentine’s Day #OOTD.

Even if this ensemble doesn’t quite line up with your Valentine’s Day plans, it’s hard to argue against the type of versatile building blocks it offers up — right? Starting with a winter blazer from Grayers gives you the flexibility to take your date (or heck, just yourself) out to drinks at a cool speakeasy or a refined sit-down dinner — or both. The stylish flannel shirt seen here is also made to be worn more casually — untucked at home, watching your favorite TV show — and it works in dressy situations, too. It could just be the best shirt for Valentine’s Day.

The same can be said for slim navy chinos from Taylor Stitch, which work for a ‘staycation’ or a night at home. You’ll also stay weather-ready with the Rhodes Dean Boots, some of the best winter boots out there — it helps that they provide great traction and killer style. We’re keeping things on-point with a slim camel topcoat, and we’re further driving home that refined aesthetic with a refined dress watch. Of course, it’s also of the utmost importance that you pick up a great gift for Valentine’s Day. And lest we forget … yes, you need good-looking underwear. Flint and Tinder can help. Feel free to let me know your plans for Valentine’s Day on Twitter — to see how I’m spending mine (likely enjoying a delicious craft beer!), you can check out my Instagram