Transitional Clothes to Take You From Wild Summer Weather to…Equally Wild Fall Weather

The end of summer is rapidly approaching, which is weird because it kind of seems like we skipped the whole season. From the pandemic to all the associated travel bans that came with it, basking in some idyllic summer paradise was a non-starter from, well, the start. But, hey. Buck up! Because the transitional season that’ll be here sooner than you know it offers the opportunity to wear some of the best stuff in your wardrobe with a lot less hassle. Think about it: When can you wear suede without overheating or risking the chance of ruining it with some unholy combination of water and snow? Light outerwear weather, baby. It’s a blessing.

And while there’s no guarantee fall will be better than summer when it comes to *gestures vaguely at the world* you’ll at least have this list to guide you on your way to a properly refreshed transitional wardrobe. (While you’re at it, you should definitely update how you moisturize and scoop some new sunglasses, too.) Mind you, this isn’t a total closet clear-out. But with a few key pieces—from jackets to sweaters to trousers—you’ll be well on your way.

Terrain-Jacquard Wool Sweater



Birthed by the genius of Samuel Ross, a former intern at Off-White, A-COLD-WALL* came to market in 2015. Since then, it’s brought us gems like this patterned sweater, made from merino wool almost as smooth as butter. The color alone is a perfect marriage of summer and fall.

Crew Neck Short-Sleeve T-Shirt



A heavyweight crewneck from the Christophe Lemaire-led Uniqlo U imprint of everyone’s favorite clothing mega-store? Yes, you absolutely should stock up on options for the warm(ish) and cold(ish) months alike.

Jacquard Medium Weight Knit Cardigan



A pattern with a whole lot of personality and some colors to match. Those are the kinds of things that span seasons, especially in the form of a just-breezy-enough linen sweater.

Long Sleeve Terry Stripe Crew in White

Todd Snyder


If you think terry stripes can only be worn in spring or summer, you’re wrong. Pair this crewneck with suede chukkas for a look that can carry you from summer to winter and back again.

Flourish Button Down Dress Shirt

Ikiré Jones


A bold-as-hell floral for all seasons. Trust us.

Manny Garment-Dyed Pleated Cotton-Twill Shorts



Seeing as September can stay as hot as August these days, adding an impeccably tailored pair of shorts to your rotation is definitely worth the investment.

Double Pleated Crop Pants



If you’re of the no-shorts persuasion, though, a simple cropped pant is all you need to jump from one season to another. This pair should be a standard for every late summer and early fall nocturnal excursion.

Slub Twill Officer Pant

Buck Mason


A well-made chino in a well-worn shade of olive green is exactly the kind of pant that can—and should—go with everything in your wardrobe, all the time.

Laight Slim Fit Jean

Mott & Bow


Light-wash jeans feel summery in vibe and autumnal in the actual material, which naturally means that the meeting of the two seasons is prime time to wear them.

Stretch Tech-Jersey Drawstring Trousers



If this summer taught us anything, it was how to be comfortable all the time. Aspesi’s trousers are made in Italy. relaxed enough for post-sweatpants life, but pulled-together enough to make it look like you finally put in some damn effort.

Fringed Western Jacket



A fringed, Western-inspired jacket is emphatically not for everyone. But it is the perfect way to channel your inner Hendrix (or other freak flag-waving style icon) this fall. Bonus: this one’s made of sueded cotton, so it’s vegan-friendly.

Sporty Pinstripe Jacket

Scotch & Soda


Pinstripes: not just for suits anymore. 

Nano Puff® Vest



Just do us all a favor and don’t wear it with a gingham shirt a la the Midtown Uniform.

Michigan Jacket

Carhartt WIP


If you’re going to get a chore coat, you might as well get an iconic one. The Carhartt Michigan coat is a workwear mainstay, and here, it gets updated by the brand’s younger, hipper Work In Progress imprint.

Slim Track Jacket

Daniel Patrick


A color-blocked track jacket is always a good idea, and that goes double when the weather is swinging wildly between “zipped-up” and “unzipped” temps.

Mio Li Sneakers



Hiking-inspired shoes. So hot right now. Hiking-inspired shoes. 

Solovair Tassel Loafer



Fun fact: Solovair dates back to 1881 and once supplied leather boots to the British army. These loafers are ideal with cropped pants and maybe a dose of dry English wit.

Suede, Leather, and Mesh Trainers

Brunello Cucinelli


Cucinelli’s trick is taking everyday items like sweaters and sneakers and rendering them in the most luxurious way possible, all without giving away the game by overdoing it on the look. These sneakers are an encapsulation of that design ethos, in a very wearable palette of cream, gray, and gum.

Wakeflex Loafer



Like your favorite Vans slip-ons, but handmade in Northern Italy by a family that’s been doing it for six generations. So…maybe a little different than the Vans.

Desert Boot

Clarks Originals


When a boot achieves internet-message-board-acronym status, like the trusty DB, you know you can count on it for pretty much any occasion. Hell, you could even wear these with shorts. Go ahead, man. Live a little.

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