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

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23 thoughts on “Online Shopping Picks: Best Men’s Henleys For Fall

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