#OOTD: How to Wear A Henley for Early Fall

It’s absolutely a must-have for the season ahead, and when you find it, you know. I’m talking, of course, about one of the best men’s henleys for fall, the subject of today’s #OOTD — and not a moment too soon. The best henley for men is ideally rugged, durable, classic, premium and yet … easy to wear nearly everywhere. How can one henley do all that? Well, you’re about to find out. We’ll show you how to wear the exceptional Todd Snyder Double Knit Henley, a fittingly sporting-inspired homage to the henley’s roots in England.

It’s since become something of a menswear classic, and if you wear it the right way (with an indigo overshirt from Flint and Tinder, for starters), you’re going to love the way you look this fall (guaranteed). You’ll see that we’re pairing it up with some of the most versatile men’s pants for a truly go-anywhere look, plus pieces like a weatherproof leather duffel bag. Things are still mighty different these days heading into fall, so perhaps this is the look to wear on a solo to-go coffee or brewery outing, or else on a socially distanced day trip (that’s where some of the best men’s boots enter the equation). At any rate, one of the best henleys for men is a surefire essential for your fall wardrobe, so let’s figure out how to wear it — shall we?

How to wear a henley for guys

Wondering how to wear a henley? Here’s how, courtesy of Todd Snyder.


The start of fall is well and truly in the air, you’ve got your new favorite henley on lock, and now, you know how to wear it — right? Yes indeed. A rugged henley for men is the perfect base layer for many a fall outfit, but I think we’ve taken it a step further with this particular piece from Todd Snyder. Things only get better when you layer it up with a rugged overshirt from Flint and Tinder for classic fall style — the best part is, you can add a Buck Mason field jacket if you really need it on a crisp fall day in the countryside. And we’re not just going with any old pair of pants here, either.

Some of the best men’s pants are the right move, and it’s great news that Myles Apparel makes a pair with plenty of stretch and durability (plus a classic five-pocket design). To stylishly tie it all together, how about a pair of the best men’s leather boots via FRYE? It doesn’t get much more premium than that. Whether you’re moving from the brewery to the apple orchard, you need one of the best men’s field watches — it’s a crucial way to finish off any #OOTD, this one included. Keeping it rolling on the accessories front, I’m always an advocate for stylish men’s socks like the ones seen above, and the Flint and Tinder leather belt shown here is as good as it gets, too. To finish it all off, grab your Filson duffel bag and hit the road. It’s (just about) as easy as that. Enjoy the season, my friends.

While you’re here: Be sure to subscribe to my twice-weekly newsletter, The Style Guide In Brief, where I discuss the best menswear, indie rock, coffee and spirits. 

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