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Yes, You Can Still Wear Shorts This Fall and Stay Warm. Here’s How

Man wearing sweater and shorts

Not wearing shorts in the fall is practically as defunct a rule as not wearing white after Labor Day. The temperatures may drop a bit in September, but think about how you felt back in April or May: at the first sign of some sunshine in the evening or temperatures above 65 degrees, we were reaching for our shorts and heading outside. Even now, if we were going for a run or a bike ride, we’d still wear shorts for our workout. Admittedly, we’re burning some calories and getting warmer in that case, but with a little layering, we can stretch shorts season right up through winter’s chill. Why? Because they’re super comfortable and unless you live in the draftiest of houses, are a great alternative to sweats for those work-from-home days. 

We’ve gathered a couple of our favorite layered shorts looks, using some of our favorite shorts from summer 2020, and adding pieces that will serve you well heading straight through the rest of the fall season. 

The Best Men’s Shorts To Wear for Fall

The shorts we’ve chosen as our foundation are two season-spanning neutral-hued pair that got us through the summer. Each offers a great fit, are super comfortable, and could go just about anywhere from the gym, to the pool, and to a fancy restaurant.

Tasc Performance Motion Travel Short

Tasc Performance Motion Travel Short

The sustainably grown bamboo viscose lightweight stretch fabric felt great, offered lots of movement and a great-looking tailored fit. 

Mountain Khakis Water Rock Short

Mountain Khakis Water Rock Short

Grab these shorts now: they’re on sale from $85. They’re quick-dry, wicking, and easy care. We particularly liked the gusset, which offered even more freedom of movement.  

Ivy League Cool

Layer a V-neck with a polo for a classic, all-American Prep look that works for just about any occasion. Take it a dapper step further with Bermuda-style, up to the knee (okay, we’ll take over the calf) socks, but update the look with a boot instead of the island’s traditional lace-up Oxfords. We also like the way this outfit brightens neutral hues with subtle flashes of color. 

Psycho Bunny Polo Shirt

Psycho Bunny Polo Shirt

You can find a polo with just about any animal embroidered on your chest, but we like Psycho Bunny’s slightly subversive, but definitely humorous message. This classic white shirt with bold accent colors transitions nicely from season to season. 

State Cashmere V-neck Sweater

State Cashmere V-neck Sweater

A classic V-neck cashmere sweater is always worth the investment, but this one from State Cashmere is an absolute bargain at $100. Best of all you can wear it on its own, upgrade a t-shirt, or throw it on over your favorite button-down. Go super-prep and throw on a striped repp tie. 

Bombas Ribbed Over The Calf Socks

Bombas Ribbed Over The Calf Socks

The dressy look helps keep your legs a little warmer and make for a neater look with pants later in the season. These are an autumnal, heathery, cotton blend; but you can go for wool for a little extra warmth.

Florsheim Lodge Cap Toe Lace Boot

Florsheim Lodge Cap Toe Lace Boot

We like this boot for its look that lands somewhere between banker and dock worker. Its matte brown finish adds a bit of polish, but the rubber outsole offers some traction should you need it. This pair also offers Suedetec linings, so you’ll be as comfortable as you would be wearing a pair of slippers. 

Indoor Outdoor 

Fall is a great time to take advantage of cooler temperatures to get outside and get some badly needed fresh air and vitamin D, particularly if you’re not into heat and have been spending the summer hiding out in the A.C. Hiking, backpacking, and spelunking have also had great influence on men’s style over the ages, from Sir Edmund Hillary to Alex Honnold. These looks are inspired by the great outdoors, but work just as well for an outdoor dining experience, a beer garden, or to look good next to your house plants. 

Howler Brothers Merlin Vest

Puffer vests are kind of the perfect layering piece, and especially in versions like this one where the quilting is more low key. Throw it on for chilly mornings, and then zip it up into its own pocket to stow it away until you need it later. The vest is also a great travel companion: keep it handy on chilly airplanes. 

Cuts Clothing Elongated Henley

Henleys are like t-shirts’ burlier cousins. They provide just as much comfort, but the simple addition of the placket adds some visual interest and sort of points right to your face. The Cuts Clothing version comes in the brand’s super soft knit fabric, and offers a slightly longer, curved hem that looks great untucked. 

Danner Light Boots

Grab these made-in-Portland boots for some serious outdoor style and performance. They’re comfortable to wear just about any time of year with their lighter nylon upper and breathable, waterproof Gore-Tex liner; but you’ll be just as happy slogging through winter storms with them. 

Smartwool Hiking Socks

Merino wool offers natural thermodynamic properties, so this pair are not only perfect to keep your feet cool, dry, and comfortable inside those Danner boots; they also include Smartwool’s seamless construction and a bit of nylon and stretch for added comfort. 

Athletic Supporter

These days there’s no reason why a certain part of your wardrobe has to be worn only at the gym. Modern workout brands offer clothes that can easily go from the bench press to the bar. This outfit allows for you to do a quick workout, pull on the sweatshirt for a video conference, and then head out for an outdoor drink with the guys 

Daniel Patrick Sweatshirt

Let’s face it, a lot of us will be wearing sweats to our home offices for the foreseeable future, even if it’s just a few days a week. Why not look as great as you feel? This one from Daniel Patrick offers a little more surface interest with its center front seam, plus this olive color is more than just a great “non-neutral neutral” for the fall season. 

Vuori Strato Tank Top

Hopefully you’ve been keeping up with those home workouts, so when you do find yourself in a situation where you’re warm enough to strip down, sport this tank that’s made from a super soft poly fiber with just the right amount of stretch and  moisture wicking to keep you dry. 

Matador Meggings

Layering leggings under shorts offers a little extra warmth as well as added support for leg muscles. You may find yourself forgoing the shorts to just wear these “meggings” as a relaxed alternative to sweats. Matador has addressed “Visible Penis Line,” the thing that makes a lot of guys uncomfortable wearing leggings alone. These also have a handy pocket to stash your phone. 

Vessi Men’s Weekend

Finish this outfit off with Vessi shoes. Even with knit construction they’re waterproof, but super breathable and comfortable. They’re even machine washable! Besides being great for around the house or around the neighborhood, these are destined to become your favorite travel shoe. If we ever get to do that again, that is. 

Rockin’ Roll

We really couldn’t do a story about wearing shorts without a tribute to Cheap Trick’s Daniel Nilsson, whose iconic 1970s look included shorts, a jacket, and an iconic cap. 

Architee Guitar T-shirt

Build your rocker crew with this guitar graphic T-shirt from Architee. With its blueprint-style Stratocaster graphics, you’ll be inspired to shredding in no time, even if it’s just with your favorite air guitar. 

Obey Pattern and Brushed Face Sweater Cardigan

We’re updating the look a bit with this patterned intarsia sweater from Obey. The abstract pattern makes it a bit more interesting than a typical fall cardigan, but the colors are neutral enough that you can dress it up with a pair of gray flannels, or down with a pair of blue jeans. 

Goorin Black Sheep Trucker Cap

Because somebody has to be the black sheep of the family. This classic trucker features the expected cooling mesh construction, with a fun graphic patch. 

Vans Mixed Media Comfycush Era

We round out the updated version of Nillson’s look with these Vans Comfycush shoes. They’ve got all that 20th century rocker crew, but offer a little more support and comfort; something we could all use a bit more of these days. 

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