The art of transitional dressing
A few thoughts on the art of surviving 50-to-80 degree swings without losing your cool.
Navigating the pre-fall weather swings
Our readers are scattered across the globe, but here in the U.S. (specifically the East Coast and the Midwest), which means it’s downright annoying to get dressed every Fall.
We’re talking 50-degree mornings that jump to mid-80s by the afternoon (or 90+ still for those of you in Florida — we’re praying for you).
My closet is confused, I’m confused, and honestly, I'm ready for a consistent cool breeze frfr.
We’re slowly climbing out of “just a tee” summer, but we’re not quite there to pull out the heavy-hitters for wintertime (thankfully). Like your parents always said: don’t wish your life away. The same applies here—don’t rush the seasons.
We’re in the sweet spot. Want to wear shorts with a hoodie? Denim shirt over a thermal?
This is onion season, baby: peel those layers off!
Transitional dressing is the name of the game, but here are a few guidelines to consider.
First, it’s about smart layering. Start with a tee, add lightweight sweatshirts or breathable cotton shirts.
Save the wools and fleeces for later (though, yes, cashmere can cut the line).
For bottoms, you can let your 16-oz. never-washed raw denim hibernate a little longer.
Stick to chinos, fatigues, or tech pants for now (the goal is interchangeability; cotton and lightweight knits are your nonnegotiables).
Color palettes matter. Sure, black and white are obvious staples, but try weaving in dark brown (this season’s hit) with navy, olive, and ecru. Yes, ecru. It’s not just for warm months anymore, it’s like the oat milk of color palettes.
Before we dive into the FW guides, here are some go-to pieces to smooth your transition from cold to hot to cold again. And here are a few practical examples of Leon, our editor, flexing in some transitional gems.
Jacket options
You don’t need to break out the Gore-Tex or go full Arctic explorer just yet. A military-inspired overshirt or a trusty denim jacket layers effortlessly over a T-shirt, sweatshirt, or OCBD.
Anything in that cropped, service-jacket silhouette instantly sharpens your look without trying too hard. Sure, a classic rain jacket with a bungee-locked hood has its place, but this season, swap it for a nylon deck jacket.
It’s like technical wear with a naval promotion, something that’s functional and sharp.
Heavyweight tees
We’re in with the triple B’s now—Big Boy Beefy tees. Talking about 5.6 oz all the way up to 8 oz monsters. It’s so much better that way. Wear 'em solo, or layer them comfortably under a denim shirt or a lightweight Harrington jacket.
Here’re a few options we dig…
V-Neck Sweaters
Maybe it’s the tidal wave of ’90s nostalgia hitting me the past few seasons, or maybe I can’t evict this image from my cerebral cortex—but V-neck sweaters are the shit. I always picture Picasso in his subtle stripes peeking out underneath.
They just work… with tees, with piqué polos, you name it.
Go for a flowier silhouette you can toss on with ease, or a more tailored one to slip under a seersucker blazer or an overshirt.
And yes, feel free to tease some clavicle while you can, because that thing’s about to hibernate until June.
Trousers
Pleats, cargo pockets, workwear pants, it’s basically summer’s encore with a teaser trailer for fall. Hefty chinos are the wardrobe’s blue-collar heroes, softening up and getting better with every wash and wear.
Don’t bench them just because the leaves are changing—keep them in rotation until that khaki shade turns into a respectable patina. Pleated trousers for an instant leg-length illusion, cargo pants for pocket-maxing, and a solid pair of fatigues in a shade of brown that is supremely underrated.
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