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!
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
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
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 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
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
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
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
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,