Online Shopping Picks: Buy One of the Best Men’s Henleys for Rugged Style

Fired up for another set of Online Shopping Picks today at The Style Guide? I know I am — let’s get to it, then. We sure do return time and again to rugged, classic menswear week after week, from stylish men’s boots to classic fall jackets. And if you haven’t caught on by now, there’s one item of menswear that can reliably team with both of those pieces. It exists in both the past and the present, simultaneously classic and modern — a stylish men’s henley. Yes, it’s rooted in British sporting tradition, but today’s best henleys feature modern fabrics and textures, plus the type of fit that goes with everything from a rugged flannel trucker jacket to your favorite fall blazer. Just see for yourself with the below picks, from brands both familiar and perhaps new to you. If you want to see some real-life tips on how to style a henley, check out my Instagram — I absolutely can’t get enough of the classic men’s henley, that much is true.  Read on and happy shopping to you!

#1. Flint and Tinder Heavyweight Henley in Navy OR Natural$62

We’re kicking off this list of the best men’s henleys by giving you not one, but TWO terrific options from Style Guide favorites Flint and Tinder. Made with carded cotton for a heavier texture — hence the name — the Flint and Tinder Heavyweight Henley is going to serve you well when it comes to fall layering. Wear the Natural Henley underneath a crisp blue chambray shirt, then pair that combo with rugged dark denim and brown leather boots, or take the Navy Henley and style it with a classic moto jacket and black denim for sleek style.

#2. Taylor Stitch Mercerized Merino Henley in Forest Stripe — $125

A well-made merino henley from Taylor Stitch in a cool fall color? Sign me up.

It wouldn’t be a list of men’s style essentials without including Taylor Stitch, right? The well-crafted Taylor Stitch Mercerized Merino Henley — a previous Style Pick of the Week entry on this site —  utilizes that modern fabric we talked about earlier, combining breathability with stylish stripes and a flattering cut. The Forest Stripe color in particular should stand out nicely underneath a dark blue denim jacket or a black denim jacket in equal measure — and of course, you can slip the Merino Henley on underneath a tan herringbone blazer for high-low office style.

#3. Billy Reid Speckled Henley — $195

A sleek henley that’s made in Italy and sharp enough to wear with a crisp blazer.

It can be rare to find a henley you can wear with a blazer — yet, the Billy Reid Speckled Henley is one that gets the job done. Made in Italy using premium fabric and refined construction, the Speckled Henley is neutral and clean enough to work with a navy herringbone or tan wool blazer quite easily. Just add slim blue denim and stylish chukka boots, and you’re set for casual Friday, casual Thursday … heck, any day that calls for laidback, business casual style.

#4.  Life/After/Denim Thermal Heney in Heather Grey — $98

A warm, casual and rugged henley for cool fall nights.

A thermal henley might be the type of classic men’s henley that first pops to mind when you think of the style. And if you want an upgraded take on this decades-old staple, the Life/After/Denim Thermal Henley is the one to buy.  Made from 100 percent cotton slub fabric in a neutral and easy-to-layer heather grey, this Life/After/Denim henley would look great when teamed up with a classic chamois shirt or a black trucker jacket for edgy, casual style. The three-button placket and side seam paneling provide some visual interest, too. Rugged AND modern? Sign me up!

#5. Levi’s 1920s Sunset Henley — $125

A durable, unique and historical henley from Levi’s — not a bad addition to your closet.

The henley itself has sporting roots, to be sure, but it’s also a truly rugged and functional staple found throughout the hardworking history of America — and Levi’s knows this well when it comes to the brand’s 1920s Sunset Henley. In this case, the maker of your favorite pair of jeans has taken a style from its 1920s archives and updated the fabric and fit. The resulting Sunset Henley is seriously cool and unique, made from a cotton-linen blend in Portgual. Wear the 1920s Sunset Henley on its own with a black moto jacket and grey denim, or style this rugged henley with rugged leather chukka boots & blue indigo denim.

#6. Bread & Boxers Thermal Henley in Navy — $32

Bread & Boxers

A comfortable, casual and cozy henley for fall layering.

We’re keeping things casual, rugged and durable once again with the sixth slot on this list, the Thermal Henley from Bread & Boxers. The contrasting cuffs and placket are a neat design touch that elevates this casual staple just a bit. That being said, this Bread & Boxers thermal henley might look best when worn with faded denim and stylish leather sneakers for a casual weekend day — heck, you can even team it with sweatpants from Bread & Boxers to complete the casual, comfortable vibes. Who’s with me?

#7. Billy Reid Hartford Henley — $95

A more affordable Billy Reid henley that doesn’t skimp on quality.

Billy Reid is back at it again on this list with the more affordably priced Hartford Henley. Don’t let the smaller price tag fool you — the Hartford Henley is just as premium a piece as the Billy Reid Speckled Henley nearer to the top of this list. This lightweight long-sleeve henley features a cotton-polyester blend, all the better for layering underneath a slim merino cardigan or a rugged indigo shirt jacket. The heather grey color of the Hartford Henley contrasts nicely with the henley’s premium horn buttons, too — not a bad design touch from a menswear master.

#8. Levi’s Refined Henley in Medium Grey Heather — $30

As easygoing of a henley as you’re going to get — made with 100 percent cotton, too.

Make no mistake about it, heather grey is a heck of a versatile color when it comes to a rugged men’s henley — that’s why we’re closing out this list with the Refined Henley from Levi’s. Available for an astonishing $30 — yes, just $30 — the Levi’s Refined Henley is a great deal for the price, what with its 100 percent cotton construction and a textured jacquard knit. Wear it with a slim blue denim shirt and black jeans, or style it with your favorite denim trucker jacket.

When it comes down to it, you need a stylish men’s henley in your wardrobe this season (and beyond).  The right men’s henley — like the durable, rugged Flint and Tinder Heavyweight Henley — merges a clean fit with excellent construction and versatility. Seriously, the best men’s henleys can work with everything a charcoal herringbone blazer and a slim topcoat to a leather moto jacket — the Mercerized Merino Henley from Taylor Stitch is a terrific choice for that type of style. Either the  Hartford Henley  or the Speckled Henley are also premium wardrobe picks from Billy Reid, while Levi’s has done a nice job with the vintage-inspired 1920s Sunset Henley. More casual henleys, like the Bread & Boxers Thermal Henley, are to be applauded, too. So, that’s our list for ya — which of the above best men’s henleys are you shopping this season? Let me know on Twitter!

Thanks for reading,

-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.

Fall 2016 Style Wish List

Editor’s note: For other seasonal style wish lists, click here.

Can you believe it’s (nearly) here already? Fall? Me neither. As always seems to come up with these seasonal style wish list posts, it feels as if I just sat down to write the last one — did you manage to pick up everything from your spring style wish list, while we’re at it? Making what can feel like the rather abrupt transition from style built for the heat of summer to style geared toward cooler climes is a luxury for some of us, but it can be just as much of a struggle if you’re looking to add transitional pieces to your wardrobe. And of course, it might still be a bit warm in your area. But fall is coming, and we’ll get to that in the coming weeks. For now, we’re still in Wish List mode here at The Style Guide. So, the below pieces are picked (sometimes) with budget in mind, but they more likely represent the best of fall style out there — according to this #menswear editor, that is. That means we’re looking for pieces that more often than not exude rugged, versatile and exemplary fall style — it’s a time for crisp breezes, crunching leaves, walks in the park, some football-viewing and beer-drinking … it’s, in short, the most wonderful time of the year (wink, wink). Don’t believe me? Read on for the below Style Wish List picks, and follow along on Instagram for more transitional style inspiration — you won’t be let down, promise!

#1. Flint & Tinder Flannel-Lined Waxed Trucker Jacket — $198

A durable new piece of outerwear that's built for darn-near anything.

A durable new piece of outerwear that’s built for darn-near anything.

Ladies and gentlemen, boys and girls — step right up, because the good folks at Flint & Tinder have done it again with this stunning waxed trucker jacket. The makers of your favorite domestically produced boxer briefs and a stupendously great hoodie have really outdone themselves this time with a beautiful piece of outerwear that’s practically tailor made for fall. The Whiskey color is rich and should look great with dark denim and a rugged henley, and the herringbone flannel lining should keep you nice and warm through all sorts of fall festivities. Feel free to rock this guy into winter, too — the Martexin 7oz. waxed sail cloth can handle a little inclement weather.

#2. Todd Shelton Classic White Oxford — $200

The ideal Oxford to offset the ideal fall jacket -- right?

The ideal Oxford to offset the ideal fall jacket — right?

This Oxford shirt right here is another Wish List-worthy piece, if only based on price alone. Every guy needs an essential Oxford shirt in his closet — we’re talking one that pairs with everything from chinos and crisp white sneakers in the summer to that durable waxed trucker jacket in the fall. Well, this Oxford fits that bill beautifully. It’s made from a substantial but breathable 100/2 ply cotton (that’s two fine yarns twisted together), and the made-in-America construction and customizable fit are huge bonuses to a piece that’s investment-worthy in every sense of the word. It’s a great piece year-round, but it would add an extra touch of crisp refinement to your favorite fall style essentials, like a shawl cardigan and sturdy dark denim.

#3. Johnston & Murphy Eldredge Wingtip Boot — $275

Italian-made leather wingtip boots that you won't want to take off? Sign me up.

Italian-made leather wingtip boots that you won’t want to take off? Sign me up.

From my recent travels to Michigan to  a Labor Day weekend in Asbury Park, Johnston & Murphy has certainly won over this style writer for blending comfort, quality and affordability. With that spirit in mind, it’s easy to see why a dependable, durable-looking and just plain handsome pair of wingtip boots makes the cut on this list.  Handcrafted in Italy, these tan calfskin leather boots are the ideal mix of rugged and refined, able to add a bit of flair to faded grey denim or a pair of slim wool trousers — try out either combination from one day to the next if you don’t believe me.  Oh, and don’t forget stylish socks that add a bit of color and comfort, will ya?

#4. Flint & Tinder Marled Long-Sleeve Henley — $62

The answer to your search for the perfect fall henley, made right here in America.

The answer to your search for the perfect fall henley, made right here in America.

Yet another piece from Flint & Tinder on this list? Believe me, the brand’s new fall collection really is that on-point. We here at The Style Guide (ahem *just me*) love a rugged henley, and it looks as if the newest addition to the Flint & Tinder line takes the cake in terms of the designated henley spot on this year’s Fall Style Wish List (only partially kidding). While it’s also available in versatile colors like Navy and Olive, you really can’t go wrong with  a classic white henley. It’s another made-in-America piece that’s going to have you covered for all sorts of style situations, particularly including pairing with a certain tough trucker jacket (can you see a theme here?). Of course, it’ll also set you right for layering under everything from a wool blazer at the office to a navy field jacket at your next rock concert.

#5. M.Gemi Netto Leather Sneakers — $228

Low-top leather sneakers in the fall? If you know how to style them, yes indeed.

Low-top leather sneakers in the fall? If you know how to style them, yes indeed.

Yes, we’re going with another pair of footwear to round out this list (although it was mighty hard to narrow it down to just five!). These sneakers are certainly a worthy Wish List — or wait list — addition, as they’ve sold pretty quickly (that seems to make them even more covetable, however). A pair of rich brown leather sneakers is a pretty underrated style accessory in fall — it’s still sneaker weather, even if at first it might not seem like it. The color of this particular pair makes them as versatile as leather chukka boots — style them with a white Oxford and navy chinos for a high-low office look, or pair them up with a crewneck sweater (and yes, even that waxed trucker jacket) for a dash of slightly dressy weekend style. What are you waiting for? Hop on them before they sell out!

Buck Mason - Timeless Design. Made in America.

Are you fully on-board with the above Fall Style Wish List picks? I certainly hope so. There’s plenty more fall style-centric content to come in the weeks ahead, particularly focused on pieces you’ll love to wear, like leather chukka boots, slim henleys and yes, a trucker jacket or two. If tackling the changing seasons at first feels daunting, look for investment-worthy pieces you can wear across all seven days of the week — dependable boots and a crisp white Oxford should certainly be on your shopping list if you don’t have ’em already, and a reliable long-sleeve henley is a must-buy (at least in the mind of this author). Everyone should splurge — truly — on a staple piece of outerwear that you can wear all season long, and that waxed trucker jacket is Exhibit A. Heck, the longer it takes me to write this post, the more ready for fall I get. If you’re in the same boat, or if you feel I missed any fall style picks, give me a shout on Twitter.

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.

The ultimate in fall style -- a great henley layered under a thick cardigan. Don't forget the standout dark denim and sturdy boots.

The ultimate in fall style — a great henley layered under a thick cardigan. Don’t forget the standout dark denim and sturdy boots.

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. As Mr. Craig demonstrates so remarkably up top, 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