#OOTD: How to Layer A Henley The Best Way for Winter

OK, so today’s #OOTD is going to tackle familiar territory for anyonoe who reads the blog regularly — we’re talking about one of the best men’s henleys, and specifically, how to wear a henley for winter. Is this the sort of topic that gets covered a lot on ye olde Style Guide? It sure is — but does that make it any less useful for the doldrums of winter? Absolutely not. You can always use more ways to wear a henley (or a refresher course, at that). The henley in question is the excellent Flint and Tinder Organic Slub Cotton Henley, a durable henley that won’t weigh you down — the sort you can layer with (as you’ll see) a classic flannel shirt and a durable waxed parka.¬† Together, these gear picks keep you toasty and sharp no matter where you’re headed, particularly if you’ve got to take on the snow during a winter weekend getaway — or on your commute, or during a daring weekend brunch run. While a rugged henley won’t cut it for scenarios where a blazer is the norm, I’m accustomed to wearing something similar to my office most days — maybe that type of look works for you, too? Regardless, you need all the layers you can get during the depths of winter (not to mention rugged leather boots, which you’ll also find below). When you feel a chill in the air, best to layer up with one of the best men’s henleys — and here’s how to do just that. For more tips on what to wear during snowy weather, check out the rest of my #OOTD series.


A classic henley helps tie everything together, does it not?

  • The Henley: Flint and Tinder Organic Slub Henley, $45.98¬†— Get one of the best men’s henleys for a heck of a deal right now, then reap the benefits — Flint and Tinder knows how to make a rugged henley that’s perfect for layering. Speaking of …
  • The Flannel Shirt: Portuguese Flannel Bravo Flannel Shirt, $91.98¬†— For chilly winter weather, you want nothing less than one of the best flannel shirts, especially in a pattern that’s elevated from the average.
  • The Parka: Flint and Tinder Sherpa-Lined Waxed Ridge Parka, $297.98 — A tough waxed parka, especially the Flint and Tinder Waxed Ridge Parka with sherpa lining, is going to keep you warm and toasty, no matter how much time you spend outside (and with an outfit like this, made for outdoor excursions, that’s going to be critical).
  • The Slim Chinos: Flint and Tinder 365 Pants, $98¬†— Yes, it’s a trio of Flint and Tinder style essentials to help this #OOTD along, but trust me: When you find slim tan chinos like these, you wear them as often as you can, all season long.
  • The Boots: Nicks Boots Americana Boots, $529¬†— For navigating slippery city streets, pull no punches with the best leather boots — heck, simply some of the best boots for¬† winter, regardless of material or construction. Nicks Boots continues to outdo itself across the board.
  • The Watch: Martenero Kerrison Watch,¬†$595¬†— Now, you’ve seen the tough Martenero Kerrison Watch on the blog before, but it’s making a return today because it’s perhaps the best leather watch to have on your wrist all winter — it’s simply as premium as it gets.
  • The Best Weekender Bag: Bespoke Post Weekender Box, $45 — Maybe you view this as the kind of ensemble to be worn for a rugged winter weekend away — or maybe not. But whether you’re hauling your everyday carry or hauling tools for a home project, the Bespoke Post Weekender Box has the carrying capacity you need.
  • The Stylish Winter Hat: Wills Cashmere Ribbed Beanie, $75¬†— Now, who said your winter hat couldn’t be stylish and luxurious (even if the rest of your gear is rugged)? No, the Wills Cashmere Beanie begs to differ — staying warm this winter never looked so good.

Alright, so was that ensemble everything you thought it would be? When you kick things off the right way — with a rugged henley, mind you — the ability to layer stylishly and in rugged fashion for winter only gets easier. Of course, it helps to have one of the best flannel shirts on hand — especially from Portuguese Flannel in a pattern that’s a touch different from what you might expect. And because you’re not spending your winter indoors in the slightest, the Flint and Tinder Waxed Ridge Parka is here to help you brave the cold in style. Yet getting back to the sleek, go-anywhere ensemble you need, slim tan chinos are here to help save the day while keeping you office-ready. The whole look also gets a much-needed lift from the best leather boots, a pair that’s at home stomping through city streets and navigating slippery terrain on a weekend excursion — the more you wear ’em, the better your pair of Nicks Boots gets. Crucially, the Martenero Kerrison Watch is a must-have in your watch collection, given that it fuses bold style with durability and dependability — plus, it looks cool as heck on your wrist. And particularly when you step outside, the Wills Cashmere Beanie is everything you need in a stylish winter hat. For when you need to get out of town (Beacon, NY is a favorite winter weekend stop of mine), gear up accordingly with the Bespoke Post Weekender Box — it’s one of the best weekender bags for your must-have cargo. Where you go and what you do in this outfit is up to you, but rest assured: It’s absolutely ready for adventure. To see what else I’m wearing this winter, head to my Instagram.

Style Pick of the Week: Taylor Stitch Mercerized Merino Henley

Taylor Stitch merino henley

Just the right amount of heft and texture for rugged fall style.

Folks. if you needed one more reason to shop Taylor Stitch, our latest Style Pick provides plenty of reasons — seriously, plenty. ¬†It’s no secret that your author, editor and creative director (ha!) at The Style Guide loves the brand for its use of quality fabrics, classic silhouettes and rugged, timeless appeal — that’s no more true than with the Taylor Stitch Mercerized Merino Henley, available for 30 percent off right now during the standout Bespoke Post Summer Sale. Not a bad deal, ehh? And what do you get for your hard-earned dollars? Plenty. Consider your search for one of the best men’s henleys over before it starts — if you buy this guy, that is. The Mercerized Merino Henley‘s success starts with, well, the 5oz. mercerized merino wool, a key point of difference compared to, say, cotton henleys. That construction makes it heavy enough to provide some texture and ¬†protection from late summer and early fall breezes. Of course, it’s also light enough to layer under a cotton field jacket or a rugged denim jacket in equal measure. That’s about par for the course when it comes to Taylor Stitch, and that’s as good as it gets. And in terms of styling potential, the Mercerized Henley is loaded with it. If you were looking for how to wear a rugged henley, I’d say this piece gives you plenty of options — just in time for fall, too. Clearly, Bespoke Post knows what’s up — agreed?

Taylor Stitch

Merccerized merino wool and a nicely made placket are but a few benefits of buying this Taylor Stitch henley.

It gets even better. With gear from Taylor Stitch, you can team any piece with practically anything else in your wardrobe. The brand’s Everyday Chambray Shirt would be am ideal layering piece atop the Mercerized Merino Henley, as would the tough, durable and fall-ready Taylor Stitch Rover Jacket. ¬†And pieces like a stylish waxed trucker jacket offer a similarly easy-to-wear styling potential. Just throw on this henley with slim, American-made denim and your favorite pair of leather boots, and you’re set. Heck, the three-button placket even helps it stand out nicely against a crisp herringbone blazer¬†or underneath an American-made Oxford. And the great thing about a slim striped henley is the simple fact that it broadens your chest and shoulders ¬†when worn on its own — a styling trick that’s no more at ease than when you want rugged fall looks. ¬†Oh, and the real kicker is that you can snag it for just $98 when signing up for Bespoke Post (versus $125 normally). That’s a heck of a deal, yeah? Yes indeed. If you’re not excited for fall after reading this, I don’t know what to tell ya. The last word is that, simply, the Taylor Stitch Mercerized Merino Henley is an essential men’s style move ¬†— even if it’s not quite fall yet.

#OOTD: Here’s The Rugged Henley to Wear This Summer

If there’s one item I reach for more consistently than any other — no matter the season — it’s got to be a rugged men’s henley. Yes indeed, in the high heat of summer (the perfect time for a short-sleeve henley) and the chilling depths of winter (hello, slim long-sleeve henley), it’s simply an easy-to-wear, effective and stylish choice. But you knew that, right? After all, we talked this spring about how to upgrade your henley. There’s no question that it can easily layer under your favorite summer blazer or be worn on its own — crucially. And today’s all-new, hyper-stylish #OOTD here on The Style Guide covers perhaps the best short-sleeve henley to buy now — or at least, consider buying. And if you read the blog frequently — and shop the hallowed halls of Style Guide friend Huckberry — you should know the brand that makes it: The inimitable folks at Flint and Tinder.

As it were, the centerpiece of today’s outfit is the Flint and Tinder Supima AirKnit Henley, done up in comfortable, breathable fabric with a modern fit. The rest of this ensemble has all the trappings of a rugged, tough outfit that someone like, say, noted henley wearer Mr. Daniel Craig might enjoy wearing.  At any rate, I hope you’re excited to check out some slim dark blue denim, classic men’s boots and a few other hard-wearing touches — including a rugged casual watch. If I were you, I’d wear this outfit out to your next brew pub crawl or even a quick day trip out to the country. And it’s even got a couple pieces — like a stylish everyday backpack — that might get you from point A to point B in many a situation. I don’t want to ruin all the fun, though. Read on below and let me know how you like these #menswear picks!

Rugged men's henley

Take your (new) favorite rugged henley and layer it with a crisp bomber jacket, dark denim and tough boots — wear it now sans jacket, and keep this look handy come fall.

The Henley: Flint and Tinder Supima AirKnit Henley, $55 — First things first: Don’t be alarmed by the use of black here! This Flint and Tinder henley is crisp and slimming, and gents like Daniel Craig  make frequent use of black tees on their own.

The Bomber: Taylor Stitch Bomber Jacket in Charcoal, $188 — If you know Taylor Stitch, you know that they excel at tough, rugged and yet wearable pieces — this Taylor Stitch bomber jacket works for cool summer evenings and chillier fall days in equal measure.

The Denim: Abercrombie & Fitch Langdon Slim Coolmax Jeans, $88 — A&F, a favorite of The Style Guide, is back with a revamped denim line featuring revamped fits — the Langdon is slim, classic and wearble in August thanks to Coolmax technology.

The Belt: Sturdy Brothers Everyday Belt in Chestnut, $80 — Lest you think accessories don’t matter … think again. The folks at Sturdy Brothers make a heritage-quality belt that happens to mesh perfectly with this look.

The Boots: Astorflex Bootflex in Dark Khaki, $190 — Quality lace-up boots made with sustainable style in mind for under $200? That’s what you get with the surprisingly lightweight Astorflex Bootflex.

(Not Pictured) The Socks: Teva Benny Gold Socks (Limited Edition), $12 — Space can be limited in our #OOTD series, but socks that offer up a pop of pleasingly bright blue should pair well with the A&F dark blue denim.

The Watch: Lum-Tec Combat B35 Automatic Watch, $799.98 — You might say this rugged Lum-Tec watch is the grandaddy of them all. Beastly looks, excellent styling potential, rugged vibes, a handsome leather strap … the  Lum-Tec Combat B35 belongs on any wish list of the best men’s gear.

The Backpack: Topo Designs Klettersack, $188 — Don’t get me wrong, I love a stylish messenger bag as much as the next guy. But if you want a grab-and-go bag for a day trip or a bar crawl — particularly when paired with a rugged menswear ensemble — the Topo Designs Klettersack could be your best bet.

The Sunscreen: Salt & Stone Sunscreen (SPF 30) , $17.99 — Sunscreen is one of those things that’s likely the last item tossed in any bag — with Salt & Stone‘s crisp design (and important functionality!), you won’t forget it again.

Have you given any thought as to where you might take this outfit? It can go just about anywhere — an upstate day trip, a trip to the farmer’s market and your local park, an afternoon at your favorite watering hole … and I’d wager it’s all because of the rugged versatility of the Flint and Tinder henley shown here. And because it can go anywhere, it’s important you grab a similarly tough bag. For instance: Take the Topo Designs Klettersack and fill it with essentials like the Taylor Stitch Bomber Jacket and much-needed Salt & Stone sunscreen. And the best part is that you can easily complement your Flint and Tinder henley with other rugged basics, from dark denim to the crisp, stylish Astorflex Bootflex. What you’ve got on your wrist is equally important — my favorite part of this ensemble might be the Lum-Tec Combat B35. And if you read this blog, you know that the details make the difference — start with a heritage-quality belt and go from there.

Let me know: What do you think of this rugged #OOTD? Drop a line in the comments!

Thanks so much for reading,


Style Pick of the Week: Flint and Tinder Slub Henley

First off: Happy Saturday, folks! And welcome to this week’s Style Pick of the Week.¬† With spring style transitions fully underway, it’s high time we layered up accordingly — right? And if you follow this blog on the regular, you’ll recognize that the right way to layer up in style this spring likely starts with gear from Flint and Tinder — true, yes? That’s definitely the case with today’s Style Pick, the essential, rugged and brand-new Flint and Tinder Slub Henley. Here at The Style Guide, we (and by we, I mean myself) love the brand for its blend of American-made quality, rugged style and classic looks. From the Flint and Tinder Texas Moleskin Shirt to more casual pieces like the brand’s Garment-Dyed Sweatpants, they’re tough to beat in terms of wearability and great looks across the board.¬† And that’s why we’re going to bat today for the Flint and Tinder Slub Henley. This piece gets quite a lot right in terms of essential spring style, from the unique Pewter color — ideal for a monochromatic pairing with slim stone chinos — to the textured slub fabric that would nicely offset stylish suede Chelsea boots and light wash denim. Yes, it certainly is a nice addition to the Flint and Tinder marled henley collection — trust me on that one.¬† Maybe if you’ve got a closet full of rugged men’s henleys — as I do — you might question the merit of adding another one. And yet … I’d say you should give it a closer look.

Beckett Simonon

Flint and Tinder

Lightweight, garment-dyed cotton and a vintage-style collar — just what you need in a spring henley!

The Flint and Tinder Slub Henley¬†has some unique styling details going for it in addition to the garment-dyed fabric and spring-friendly colorway. The three-button collar on the Flint and Tinder Slub Henley¬†calls to mind a band-collar shirt — and of course, a band-collar shirt might just be the one shirt to add to your closet this season. It’s a slightly vintage look that would fit right in with dark blue selvedge denim and your favorite pair of worn-in leather boots.¬† And the good news is, the lightweight American cotton construction of the Flint and Tinder Slub Henley¬†should provide some leeway in terms of spring layering — for example, a lightwash denim jacket and perhaps the famous Flint and Tinder 365 Pant could make for a nice weekend ensemble.
On the other hand, you could easily slide it under a stylish chambray shirt for a spring bar crawl,¬† or pair it with a tough spring jacket — say, a field coat — for on-the-go wearability. And like other Flint and Tinder gear, you’re getting an agreeable price for truly excellent quality — $58 isn’t the worst price in the world for a piece that can be mixed and matched with a¬† lightweight navy blazer or a slim leather moto jacket in equal measure. Again, it’s tough to top Flint and Tinder gear across the board — let me know via the comments if you’re picking one up, or¬†drop me a line on Twitter if you’ve got questions on how to style it. All good? All good.

Cheers and thanks for reading!


#OOTD: The Best Way to Wear A Henley This Fall

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 will take one great item and put together a versatile, stylish outfit around it. Look for past features here.

So it’s not exactly the middle of summer anymore, is it? That’s a strange sensation if you’ve been used to dressing for the heat or packing up stylish beach gear. But if¬† you’re anything like this #menswear writer, you relish the chance to dress for seasonal transitions and break out some of your favorite seasonal style staples. We’re talking pieces that are rugged and refined, ready for casual wear or able to be worn with a bit more tailored style in mind. And in the case of this week’s #OOTD, we’re looking at an outstanding piece for a seasonal transition — the ever-reliable slim long-sleeve henley.¬† With its athletic-minded origins and rugged good looks, a great henley certainly works in the summer¬†as well as the in-between period between summer and fall. But particularly when it’s made with marled fabric and plenty of quality and comfort, it’s the ideal early (and middle, and late) fall style piece — think of the below #OOTD as a weekend workhorse look. To get your mind right when it comes to¬†stylish henleys,¬†check out last year’s picks for the best men’s henleys for fall¬†— and know that we’ll have a similar feature coming on this site in the weeks ahead. Oh, and how exactly should you style this durable staple? We won’t drop any hints up here — scroll below to check out the #OOTD, join in on the men’s style conversation at The Sty le Guide’s Facebook page, and check out this guy’s Instagram for daily style tips.

Best men's henleys for fall

Just one way — but perhaps, the best way — to wear a henley this fall.

The Henley: Flint & Tinder Marled Long-Sleeve Henley, $62¬† — So, the henley shown here is a bit more expensive than you might be used to paying for a basic layering piece. But the quality, fit and styling potential is top-notch, and given the fact that it’s part of a slew of new additions to the Flint & Tinder product line, you should definitely pick up this slim henley.

The Coat: Old Navy Canvas Coat, $69.94 — It might initially be too hot to wear a canvas coat atop that henley, but know that when it gets slightly chilly and you need a crisp top layer, this rugged canvas coat is the perfect finishing touch.

The Chinos: JACHS NY Grey Bowie Fit Stretch Cotton Chino, $89 — Why go with chinos here as opposed to slim, dark denim? They lend the look a bit of high-low style appeal, and the fabric and slim fit are nice positives.

The Boots: CAT Footwear Russell Boot, $150 — Boots that blend different fabrics and textures (like wool and leather) with a sturdy ankle boot, moc toe combination are the perfect way to nod toward the chillier temperatures of fall — not to mention the rugged-refined vibe of this outfit.

The Socks: Flint & Tinder Inventor Socks, $17.98 (Three-pack) — If we’re going with a Flint & Tinder henley, might as well go with crisp, stylish and comfortable Flint & Tinder socks, ehh?

The Watch: Timex x Red Wing Waterbury Chrono, $158 — The Timex x Red Wing Heritage collaboration is a certified Style Guide favorite, and it’s the perfect mixture of toughness and style to offset the other fall-appropriate pieces in this #OOTD.

The Belt: Anderson’s Stretch Woven Leather Belt, $195 — If you want a belt that’s going to work as hard as you do, last forever (truly) and add some subtle texture to this overall look, the Anderson Stretch Woven Leather Belt is the way to go.

The Everyday Carry: United By Blue Lakeland Laptop Bag, $119.98 — Looking for a durable, dependable bag to haul around your laptop? This United By Blue laptop bag merges function and fashion, and it does so while promoting a good cause (the brand removes one pound of trash from oceans & waterways for every item sold).

Are you ready for some fall weather yet? Hopefully so. Dressing for the transitional period between the heat of summer and the chill of winter can seem taxing if you’ve grown used to wearing that short-sleeve chambray shirt for months on end, yet reaching for the right pieces can make it an enjoyable task. A marled henley is an essential for the colder months, and when mixed with dependable boots and refined chinos, it can work in even more style situations. On top of that, sharp socks that add a pop of color play nicely off dressy touches like that textured leather belt and rugged leather watch. And if it gets truly cold in the weeks ahead, you can always add a crisp shawl cardigan to this same ensemble. Have questions or more suggestions for the #OOTD series? Shoot me a note on Twitter.

Make room in your closet for a great henley — and stay stylish in the meantime!


Online Shopping Picks: Rugged Men’s Henleys for Summer Weather

What started as a functional shirt for British rowers is now a style staple. Short-sleeve olive henley by Pistol Lake. Dark denim by Mott & Bow. Glasses by Warby Parker. Stainless steel dive watch by Invicta.

What started as a functional shirt for British rowers is now a style staple. Short-sleeve olive henley by Pistol Lake. Dark denim by Mott & Bow. Glasses by Warby Parker. Stainless steel dive watch by Invicta.

So this site just ran an Online Shopping Picks piece awhile back detailing the best T-shirts for spring and summer¬†— so what makes a henley different than a T-shirt? It’s all in the details. By its nature, a henley, with a two-to-four-button placket on the front, has slightly different visual details than even a pocket T-shirt — and it can sometimes get boring to wear pocket T-shirt after pocket T-shirt (take it from a guy who has about five). The henley has evolved from its origins as sportsman’s shirt into a symbol of rugged 21st-century style — check out how Daniel Craig¬†and Chris Pratt rock the style, for starters. While one shirt won’t turn you into a dinosaur-fighting badass, it doesn’t hurt to emulate that move — and the five selections below just might help you do that.

#1. Buck Mason Short Sleeve Henley in White, $45

Made in the USA the right way for a fair price.

Made in the USA the right way for a fair price.

Just as with Buck Mason Oxford shirts, this henley is made in the U.S.A and is but one of the many excellent basics the brand has updated for modern times. The Pima cotton keeps this shirt soft, while small details like a rounded hem, a clean four-button placket and ribbed cuffs at the sleeves all set it apart from more typical henleys. This is the type of shirt you can wear on its own now with rugged denim or slim chinos, and continue wearing under cardigans (a la Mr. Craig) well into the fall and winter.

#2. Pistol Lake Short-sleeve Henley — $35

Rugged and deeply cool at the same time, and made in America on top of that.

Rugged and deeply cool at the same time, and made in America on top of that.

You very well might recognize that henley from the above picture, or from this spring Style Pick post. It keeps popping up simply because it’s just that good — as far as made in the U.S.A quality for the price, there’s nearly no better value out there than what the dudes at Pistol Lake are doing. While the olive (or Quartermaster)¬†number has proven excellent and versatile on a personal note, the Faded Black colorway¬†would be the epitome of rugged downtown cool when paired with grey jeans and some white sneakers¬†— the unfinished sleeves are perfect for rolling or styling as you please.

#3. J. Crew Slim¬† Broken-in Short-Sleeve Henley — $34.50

A decidedly brighter shade than other options on this list.

A decidedly brighter shade than other options on this list.

Unlike its counterpart above, this J. Crew henley isn’t made stateside. It does, however, boast a cheaper price, a range of colors to pick from and a seasonally appropriate sunfaded wash. The faded black, navy, red and white colorways all have a large range of sizes available (rather surprisingly), but the red color would be an interesting change of pace and still wearable with navy or light grey chinos and leather sneakers¬†for a high-low look.

#4. Steven Alan Self-Placket Henley — $48

A deep indigo blue color with some unique, sporty touches.

A deep indigo blue color with some unique, sporty touches.

What’s got the texture and striped pattern of a polo, but the more laidback design of a henley? This lovely Steven Alan piece, that’s what. It’s made from a heavier textured cotton blend, so it might not be nearly as breathable as the other options shown here, but it’s got some neat styling touches. The shorter two-button placket adds an almost retro look, while the heavy textured cotton creates a microstripe pattern — can a regular henley do that? Nah. At $48 on sale (marked down from $125), it’s a little pricier but¬†honestly still¬†a downright steal.

#5. Billy Reid Pensacola Polo in Steel Blue, $78

A cool sky or (Steel) blue color and designer details like Mother of Pearl buttons make this a standout piece.

A cool sky or (Steel) blue color and designer details like Mother of Pearl buttons make this a standout piece.

Unlike some of the other entries on this list, this piece isn’t made in America — it’s made¬†at the source in Peru though with heathered Peruvian cotton.¬†It’s the priciest of the bunch by a good amount, but the side vents and four-button placket actually make it a bit dressier — and more versatile, by default. This piece should wear a little more like a polo, so that means you can and should take it for a spin with a khaki blazer. The contrast stitching and mother of Pearl buttons also upgrade it slightly — and with Billy Reid, you know you’re getting quality.


Now if none of these options float your boat (or you don’t fancy spending close to $50 on a henley), be sure to give old standbys like Old Navy or Target a look — you’re getting fairly solid quality for low prices and the option to buy a few at a time if you’re into that sort of thing. On the more lux end of things (but just missing the cut on this list), Club Monaco does a linen henley in a dark blue that you could even wear with, say,¬†a light grey linen suit.

What are your thoughts on this list? Which of the above options would you (or will you) pick up? And what’s your favorite way to wear a henley?

Ben Sherman US