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

Style Suggestion: Labor Day

Perhaps the best representation of the kind of gear you should have on-hand for the weekend. French Terry Sweatshorts by Pistol Lake. Stainless steel dive watch by Invicta. Sunglasses by Randolph Engineering. Vintage ballcap by Goorin Brothers. Brass bottle opener by Owen & Fred. Two-Hearted Ale by Bell's Brewing.

Perhaps the best representation of the kind of gear you should have on-hand for the weekend. French Terry Sweatshorts by Pistol Lake. Stainless steel dive watch by Invicta. Sunglasses by Randolph Engineering. Vintage ballcap by Goorin Brothers. Brass bottle opener by Owen & Fred. Two-Hearted Ale by Bell’s Brewing.

Well folks, it’s almost upon us. The de facto end of summer — Labor Day. That means fall style is well on its way (including an updated 2015 Fall Style Wish List), which is quite exciting as far as the potential it brings for layering and new outfit combinations. However, that also means there’s one last chance to bust out some casual, long weekend summer style. Whether you’re hitting the beach, the pool or a backyard barbeque, you can’t go wrong with trying to look your best — ya dig? Take a look at the below suggestion and feel free to share what you’ll be wearing when the  time comes!

The Shirt: Pistol Lake Short-sleeve Henley — $35

The perfect shirt for a laidback weekend. Dark denim by Mott & Bow. Stainless steel dive watch by Invicta. Glasses by Warby Parker.

The perfect shirt for a laidback weekend. Dark denim by Mott & Bow. Stainless steel dive watch by Invicta. Glasses by Warby Parker.

So this henley keeps popping up on this blog time and again, but for extremely good reason (see a rundown of other great henleys here). It’s the ultimate masculine style piece for warmer weather, what with its athletic cut, unfinished sleeves (giving it a vintage look) and a worn-in vibe that perfectly complements a casual weekend fit for a barbeque or some time at the beach. If the occasion does call for something dressier, you could throw on a crisp polo instead. Any of the brand’s neutral colors would work well for this henley, but the Relic White or Quartermaster options are particularly versatile.

The Shorts (or Swim Trunks): Pistol Lake French Terry Sweatshorts — $55 OR H&M Solid-color Swim Shorts, $12.99

On the left: A sporty pair of sweatshorts that allow for flexibility and casual style. On the right: Cheap swim trunks that can easily be replaced.

On the left: A sporty pair of sweatshorts that allow for flexibility and casual style. On the right: Cheap swim trunks that can easily be replaced.

Why the two different options listed? Well, let’s say you don’t happen to be at the water but still want to look good — not too dressed up or dressed down. A French Terry sweatshort (as seen on GearHungry) allows you the flexibility to move around and play some backyard football, say, yet it’s an upgrade over baggy cargo shorts or athletic shrots. Some lightweight shorts in a neutral color (like any of the options seen here) could stand in as well. The swim trunks, on the other hand, are the type of thing that could be a quick pick-up if you need a replacement pair of trunks — or just a pair in general. And at that price, they can very easily be replaced when swimming season rolls around again (for those of us in colder climes).

The Shoes: Sperry Authentic Original Fleck Canvas 3-Eye Boat Shoe — $90

A sneaker-boat shoe hybrid from a brand that does boat shoes the best.

A sneaker-boat shoe hybrid from a brand that does boat shoes the best.

Unlike the swim trunks listed above, $90 is actually quite a bit of an investment to make for a canvas boat shoe at this point in the summer. But if you don’t mind hanging on to them until spring rolls around again, then these could be a good pick-up from a well-known brand.  Boat shoes haven’t gotten a ton of airplay on this blog, but the style would blend in better with swim trunks than a pair of classic sneakers — although if you go the sportier route and opt for something like sweatshorts, crisp white sneakers certainly wouldn’t be amiss. And with either option, you could opt to go barefoot or grab some Richer Poorer no-show socks that do a nice job staying put.

The Watch: Stuhrling Original Aquadiver Manta Ray Watch — $83

The Stuhrling Aquadiver Manta Ray watch.

The Stuhrling Aquadiver Manta Ray watch.

This watch, like some of the other items here, has indeed been featured on this blog quite a bit (read the original review here). But, there might not be a better (or quicker-shipping via Amazon) rubber strap watch out there. It again meshes with the sporty-casual vibes of this outfit and looks particularly rugged when paired with swim trunks (James Bond wears a rubber strap watch in Casino Royale, as you might recall). Other tough-casual options are out there as well — the Timex Cordura Ripstop watch (a new release this summer), which adds a bit of sheen with a blue dial. Subbing in a NATO watch strap with some pattern also could work if you already have a preferred casual watch.

The Sunglasses: J. Crew Factory Navigator Sunglasses — $14.50

A retro frame shape and color make these one heck of a pair of shades for the price.

A retro frame shape and color make these one heck of a pair of shades for the price.

Under $15? For a J. Crew (well, close enough) pair of sunglasses? That’s a downright steal, and plays into the notion of grabbing something on the cheap for the weekend. That way, you won’t feel bad should they break or get stepped on. This pair in particular combines a retro-looking square lens shape with an equally retro gold frame for some pretty neat style. If buying goods made to last is more your thing, the Concorde Flash Lens series from Randolph Engineering hits the mark for a pair that’s made in America and exceptionally solid. If you want even more retro flair however, J. Crew Factory also offers a pair of Clubmaster-inspired frames for a low price.
Florsheim
Of course, if the situation does call for an overall dressier look, throwing on some slim chinos should dress up that henley (or polo) nicely. And if you are hitting the road, make sure you prepped to do so in style with these great men’s travel essentials. Above all though — enjoy this last hurrah (or perhaps the first of many fall …. hurrahs?) and do so in style!

What are your thoughts on the above outfit suggestion? What pieces would you change or swap out?
Ben Sherman US
Greats