#OOTD: How to Dress for the First Snowfall

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.

Can you feel it? A real chill in the air? Temperatures (nearly) below or *gasp* at freezing? And maybe … the flutter of a snowflake or two? Yes, the more you look around these parts — that is, Brooklyn — on The Style Guide, the more you realize winter’s just about here. Of course, if you find yourself in a warm climate year-round, stop reading — we have plenty of beach-ready menswear for you. But if you need to bundle up for that first snowfall, the #menswear you need is just a few clicks away — and it looks sharp for situations casual and slightly less so.  Essential layering pieces like a shawl-collar cardigan and a slim henley can work all through fall, but when it comes time to combat the snow? You can certainly still reach for ’em with confidence. We’ll get to the full #OOTD below — and for style inspiration on the daily, check out the behind-the-scenes process on Instagram.

Layering up for snowy weather with a comfortable henley, a rugged cardigan and waterproof boots.

Layering up for snowy weather with a comfortable henley, a rugged cardigan and waterproof boots.

The Cardigan: JACHS NY Donegal Shawl Neck Cardigan, $129 — With its combination of hefty fabric yet a pleasingly modern fit, this cardigan is refined enough for the office but casual enough for the weekend.

The Topcoat: Old Navy Wool-Blend Topcoat in Crème Caramel, $124.94 — Add another brand to your list when it comes to stylish topcoat shopping this season. Old Navy knocks it out of the park with this functional, sharp number. Is it a heavy, technical parka? Not quite. But will it layer up nicely and look refined along the way? Yes, sir.

The Denim: Flint & Tinder All-American Jeans (Slim Tapered or Straight Tapered), $98 — If you caught this site’s post on the best men’s selvedge denim, then you know how essential Flint & Tinder jeans can be. Snag either the Straight or Slim Tapered cut and wear them all season. As to a belt? Choose a braided leather belt  for seasonally appropriate texture if you’ve got one.

The Henley: OLIVERS Apparel Convoy Henley, $98 — If you’re heading to the office & a henley won’t cut it, sub in a stylish chambray shirt & a wool tie. But in casual situations? Layer away with this soft, comfortable and slim henley.

The Boots: Cole Haan Lockridge Moc Toe Waterproof Boots, $350 — Perhaps more well-known for lightweight shoes like its ZeroGrand series, the Lockridge is a flexible, durable and completely waterproof boot ready for snow and slush, plus a business casual day at the office.

The Socks: Anonymous-ism Fair Isle Grade Crew Socks, $25 (Available via East Dane) — With various shades of blue in this outfit — plus that rich camel topcoat — a shot of red via textured socks makes a nice addition.

The Watch: Lum-Tec M60 GMT Watch, $499.98 — If you stop by here often, you know that Lum-Tec makes a bevy of watches that are Style Guide favorites. Although brown boots are in play, the M60 GMT Watch features a black dial and a black leather strap– but it comes with a stainless steel bracelet or a black rubber strap (especially handy in the snow).

The Hat: Herschel Supply Co. Abbott Knit Beanie, $20 (Available via East Dane) — Other than stylish leather gloves, what’s the one accessory keeping you warm in the blustery snow? A functional, neutral winter cap. If you’re going to go investment-level with a durable casual watch, might as well keep your hat affordable and versatile.

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This snowfall-ready outfit favors fashion just a bit more than function — we’re not throwing on a blizzard-level parka and snow pants just yet. But in the event it does start to snow a little harder, versatile accessories like a warm shawl collar cardigan and a sharp topcoat should serve you well. And accessories like tough winter boots  and a rugged leather watch can certainly take a few punches. Regardless of whether you’re stepping through  a few flurries or the bitter chill, don’t leave home without a warm scarf and gloves (thank your mom for that reminder, too!). If you’ve got other questions on what to wear for the first snowfall, or just want to chat, shoot me an email or a Tweet.

Stay stylish!

-Beau

The Friday Read: Veterans Day, Sword and Plough and Glenfiddich Whisky

Editor’s note: Expect these posts once a week on Fridays — consider this a jumpstart on reading for your weekend downtime. Expect a mix of style and non-style content. For more entries, click here.

Well. Hey, what a week, right? Onward and upward. On this Friday, it’s a good reason to reflect and bring us all togehter– Veterans Day should bring with it great appreciation for the men and women who’ve served, and continue to serve so bravely. And a bit of a focus on the lifestyle companies that help support those veterans never goes wrong, either. Is there anything better than buying stylish, quality menswear for a great cause? If you’ve got some plans to do that this weekend, I think you’ll like the content we have in store below. And if your weekend brings with it other plans, it still pays to keep in mind some crucial men’s style tips — like how to dress for fall travel, or how to buy your new favorite henley (all crucial, you see). And if it’s getting really chilly where you are? Layer up with a stylish flannel shirt or a slim cardigan. You can, of course, look for our weekly Style Pick tomorrow — and stay tuned, ‘cuz it’ll get you shopping via Huckberry quicker than you can move your mouse. For now, catch up on the week in menswear — and the weekend to come.

A duffle built with military-grade fabric and inspiration.

A duffle built with military-grade fabric and inspiration.

    • First up in our Veteran’s Day rundown? A company that keeps the sacrifices of our armed forces front and center in everything it does, from its use of repurposed military fabrics to its mission of supporting vets through all phases of production. Sword and Plough  is launching a new duffle bag inspired by co-founder Emily Nunez’s experience with her U.S. Army duffle. It’s built with that same durability in mind and available in either Camo or Olive — the Camo version is lined in surplus 500-denier nylon fabric, while the Olive version is lined in a surplus cotton/nylon twill (originally meant for older military uniforms, but unused).  Oh, and the leather accents even come from the brand’s Redwing, Minn., which itself is a major military supplier. Get it ASAP via Sword and Plough, and know that the brand’s weekender bags — one of which I took with me on a fall trip to Providence — are just as quality.

  • If you fancy yourself in the market for a smaller accessory that pays homage to military inspiration you can’t go wrong with a rugged, durable and stylish casual watch via AVI-8.  Makers of handsome timepieces, they’re offering 30 percent off the brand’s Flyboy Collection now through Monday, November 14th using the code ‘Flyboy‘  — of course, as to the watches themselves, you can’t go wrong with the Flyboy Tuck, inspired by Royal Air Force flying ace Robert Stanford Tuck. The Flyboy Mesh is also clean, crisp and stylish enough for both casual and more refined wear. What are you waiting for, yeah?
  • Now, it’s not quite Veteran’s Day-related, but your footwear closet might need a new addition. CLAE and Style Guide favorite JackThreads just teamed up on a stylish sneaker collaboration that’s in need of your time. The CLAE x JackThreads Bradley is a refined low-top black sneaker with a patent leather cap toe and heel — not your everyday set of kicks. And the CLAE x JackThreads Strayhorn Mid is a unique, affordable and super-stylish high-top chukka sneaker with a wool upper. Yes, you’ll want to wear this with a classic chambray shirt, your favorite cardigan and dark denim soon — very soon.

Want one last way to toast to the weekend?

  • Craft bee is a big passion of mine. Whisky? Not all the time. But whisky aged in craft beer barrels? Bingo. See, we’re not all menswear here at The Style Guide. If that’s the case for you as well, you’d be wise to keep your eyes open for the new Glenfiddich India Pale Ale Cask Finish, a single malt scotch whiskey finished in IPA craft beer barrels and released last month. It’s part of the Glennfiddich Expermental Series, and it’s certainly got the rich flavor and nuanced details to back it up. It’s now out in the public, too  — keep your eyes  open for it at luxury whiskey retail stores, along with premium bars and hotels across the U.S. Cheers!

That brings us to the end of this week’s Friday Read — again, stick around for tomorrow’s Style Pick of the Week, and stay stylish!

-Beau

Online Shopping Picks: The Best Henleys to Buy Right Now

Editor’s note: Start your seasonal menswear shopping here.

So, we’re into November here on The Style Guide. There’s a chill in the air, the holidays are around the corner (crazy!) and maybe, just maybe, you’ve noticed a piece or two missing from your cold-weather wardrobe. Now, we talked tough denim shirts last week, and we’re talking another choice menswear essential today. You might have tough high-top sneakers and slim selvedge denim covered this season– maybe even a stylish fall cardigan — but what else are you going to layer it with? The answer’s pretty simple, and it’s one that comes up here often on this site. It’s rugged, it’s durable and it makes just about any guy look great – the essential long-sleeve henley, folks. While we’ve covered the best short-sleeve henleys and even took a stab at rounding up stylish henleys last fall, it’s high time for an update. The layering potential of a slim henley is such that you can pair it with a cotton peacoat, a V-neck sweater or underneath a chambray shirt without missing a beat. And if you get one that’s made with quality materials and attention to detail — like the picks below — you’ll have an easier and even more enjoyable time wearing it. Want to chime in on the conversation? Head over to The Style Guide Facebook page for a spell, or hit up Instagram for more.

#1. Flint and Tinder Marled Long-Sleeve Henley — $62

One of the best henleys on the market, and sold by the great Huckberry team, to boot.

One of the best henleys on the market, and sold by the great Huckberry team, to boot.

Our top pick here is almost too easy of a choice. Sold by the folks at Huckberry, the Flint and Tinder Marled Long-Sleeve Henley is as good as it gets. With a unique, visually interesting four-button placket, a  trim-yet-mobile fit and nicely marled mid-weight jersey fabric, it’s sure to become your  new fall go-to. Heck, you could pair this stylish henley with a pair of Flint & Tinder selvedge denim and a rich suede bomber jacket for excellent style nearly any day of the week.

#2. Reigning Champ Long Sleeve Henley — $85

Made in Canada with all the reliable style details you could ask for.

Made in Canada with all the reliable style details you could ask for.

Like Flint and Tinder, Reigning Champ knows a thing or two about reliable, well-crafted basics. Its Long Sleeve Henley is no exception, made from soft cotton in a seasonally appropriate olive color. It’s the type of henley to throw on underneath a chambray shirt, or on its own, with brown leather sneakers for a weekend coffee run. The raglan sleeves are a flattering touch that’ll broaden your shoulders, and a scalloped hem is another neat visual touch. It’ll also work nicely in the early days of spring — keep it around for the fall and beyond.

#3. Grayers Byron Double Cloth Henley — $59.98

Easygoing, essential and stylish. The Byron Double Cloth Henley definitely gets a lot right!

Easygoing, essential and stylish. The Byron Double Cloth Henley definitely gets a lot right!

It’s only fitting that Grayers — so named for the flannel trousers worn casually by young British men in the ’50s — makes a heck of a nice henley. It nods to the style’s real-life sportswear roots, yet does so with the modern fit and excellent fabric that’s become a hallmark of the Grayers brand. The Byron Double Cloth Henley is lined with soft cotton jersey and features a heather slub fabric that’s the right weight and feel to team up with a Grayers blazer., for example. The price on the Double Cloth Henley isn’t half-bad for a quality layering essential, either.

#4. Alex Mill Indigo French Terry Mock Henley (Available via East Dane) — $125

Part sweatshirt and part henley -- but there's really no wrong way to wear this Alex Mill piece.

Part sweatshirt and part henley — but there’s really no wrong way to wear this Alex Mill piece.

If you’re unfamiliar with Alex Mil, it’d be a wise bet to get acquainted. Particularly if you like ridiculously well-made basics that add a touch of continental flair, the French Terry Mock Henley is worth checking out. It’s made from, as the name would suggest, lightweight French terry fabric in a deep indigo wash — it’s part sweatshirt, part henley and stylish  no matter how you slice it. Layer it over a classic blue Oxford or a tough chambray shirt for rugged-refined office style.

#5. Todd Snyder Classic Chambray Henley (Available via East Dane) — $125

An excellent mix of the heritage-inspired and the modern from Todd Snyder.

An excellent mix of the heritage-inspired and the modern from Todd Snyder.

In the midst of his excellent work with collaborations like the Timex x Todd Snyder Mod Watch, it’s easy to forget that Todd Snyder still makes excellent basics in his own right.  The Classic Chambray Henley is virtually a classic Snyder piece, right up there with the Todd Snyder x Champion Pocket Sweatshirt. Why’s that? Well, it mixes classic sportswear touches — like a elongated placket and a modern fit — with neat chambray detailing at the collar. It’s a premium piece that’s so well-made, you could even get away with wearing it under a wool blazer in the colder months ahead.

Although plenty of people think of the henley solely as a casual piece, the above selections are well-crafted and feature enough visual detailing that they’d work quite well underneath a fall and winter blazer or a slim cardigan on a casual day at the office. And for the investment you’re making, it’s worth it to get as much wear out of it as possible. Pieces like the Flint and Tinder Marled Long-Sleeve Henley are top of the line, made in American out of premium materials. And a hybrid piece like the Long Sleeve Henley  from Reigning Champ mix in fall-appropriate color and texture. Those types of touches are exactly what you should be looking for in a stylish henley — and hopefully, the above picks are enough to get you started.

Until the next post — thanks for reading!

-Beau

Buck Mason - Timeless Design. Made in America.

#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!

-Beau

Online Shopping Picks: Best Men’s Henleys For Fall

Editor’s note: For more Online Shopping Picks covering essential categories in the menswear world, head here.

It seems as if it was just yesterday I sat down to write about rugged men’s henleys … for the summer. The summer. And yet here we are looking toward October, and that means weather that might not start too bad, but often ends rather frigid. For all those times, a henley really is one of the best layering bets a guy can place for the fall and winter.

Although some brands are making lighter-weight henleys now, it always seems best to me to wear a long-sleeve number in colder temperatures. And there are options at every price point that can add a dash of rugged appeal to just about any situation — including under a blazer or with other sportswear staples, like a baseball-inspired cardigan. The following picks encapsulate a wide price and quality range, but whether you’re a henley-every-day kinda guy or just on some days of the week (say, Wednesday?), I hope you find what you’re looking for.

#1. Pistol Lake Henley — $40

A style that closely mimics the one seen on Mr. Craig -- without the high price tag.

A style that closely mimics the one seen on Mr. Craig — without the high price tag.

Just as seemed to be the case with the best men’s short-sleeve henleys, so many of the best long-sleeve options are being made by brands who emphasize both sportswear staples and made-in-America manufacturing — like Pistol Lake. This particular henley was seen on this blog back in March, and it’s just as relevant a pick now that it’s nearly the depths of fall. The brand uses a premium 6 oz. jersey cotton for this henley, and it’s got a trim, athletic cut that should flatter many body types. In a crisp white color that still retains a vintage feel, it’s the sort of piece that’ll look great with high-low combos like slim grey trousers and high-top sneakers later on this season.

#2. Todd Snyder Classic Henley in Indigo — $125

An of-the-moment color with unique finishing touches like a chambray placket.

An of-the-moment color with unique finishing touches like a chambray placket.

We jump right from a pretty affordable option to a … not-so-affordable option in slot number two with this piece. But it really is the kind of henley where you can expect to get your money’s worth and more. It looks to be cut and made so well that you could even rock it with tailored wear (the types of looks that were seen at Todd Snyder’s SS16 presentation this past summer). The chambray trim and roll cuffs are two neat design touches that should help it wear more like a sweater than a true henley, and if you’re paying that much for it, you should absolutely toss it on over a white Oxford cloth buttondown in lieu of a sweater on casual Fridays.

#3. Target Olde School Long-Sleeve Striped Henley — $20.98 to $25.48

Nothing eye-popping about this henley except the low price -- a good thing!

Nothing eye-popping about this henley except the low price — a good thing!

So for those of us who are indeed on the hunt for an affordable option (#menswear bloggers be damned), Target delivers the goods — although I’m not sure who Olde School is. Regardless, there’s nothing too fancy about this henley, which features a three-button placket and is made from 100% cotton. The chest stripes make any guy look better by accentuating the shoulders & chest, adding some bulk to your frame — that’s a wise move when considering the heavier textures of fall blazers and sweaters. And at that price, you could pick up two for the price of one Pistol Lake henley (good if you just throw them on from time to time). Note that you could also pick up a henley from the Merona line for about $10 cheaper.

#4. Old Navy Henley — $19

Another option that keeps things simple. But not stupid.

Another option that keeps things simple. But not stupid.

Our fourth entry in this post keeps things on the affordable and simple front, with the emphasis on both of those categories. Old Navy sticks to reliable basics that don’t break the bank (more on that here) and from personal experience with these heathered henleys, they’re a reliable option, particularly for layering. If you like an exceptionally sturdy collar on your henleys, these don’t quite have that — but the fabric is surprisingly soft on the plus side. You’d also be surprised at how much mileage you’ll get out of a color like a rich burgundy, particularly with neutral trouser options like grey and navy. Of course, you can purchase another Starbucks drink if you spring for the Light Grey Heather option instead.

#5. Life/After/Denim Hachiko Henley — $88

As simple as it gets -- even more minimal thanks to the two-button placket.

As simple as it gets — even more minimal thanks to the two-button placket.

Life/After/Denim is one of those curious brands that people seem to love if they’ve heard of — and are instantly drawn to if they haven’t. I first came across the brand when researching them for a piece on printed shirts for spring, but they do casual basics well, too. The shorter-two button placket on the Hachiko Henley is a bit more eyecatching than most shirts of this style, so it’s a piece that would probably do better on its own or with a simple cardigan. The tri-blend jersey cotton should be soft yet not as stifling as a thermal henley, and the color should  do great with both black jeans and regular old dark denim.
Ernest Alexander
With any list of online shopping picks, there are only so many brands that make the final cut. As always, the excellent and ethically made selection of basics at Apolis continues to impress, and the brand’s Stripe Long Sleeve Henley just missed the cut. The equally impressive basics purveyors at Buck Mason are also onto something with the Navy Henley they’re stocking this fall — better luck next time? Either way, there’s definitely a henley out there for you this fall and winter, even if you’re not built like Daniel Craig *yet.*

Which henley or henleys are you planning on grabbing this fall? How would you layer this staple piece?

Ben Sherman US

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.

Florsheim

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