There’s a moment when it becomes clear that fall is here. I open the door and the different-over-night weather winks like a grandpa and asks me where my jacket is. Soon I remember how comfortable (and easy to style) layers are and it's like Ralphie waking up and it's Christmas season. This is Fall Getup Week.
This is the part of the year where clothes stop being things you tolerate and start being things you choose. Layering becomes possible, shoes with some heft return from their seasonal exile, and jackets finish outfits like Bond's bow tie. There’s texture, there’s structure, there's comfort, and for once it feels like the effort has a payoff.
This Year’s Style Creative Direction
If there’s a plot this fall, it revolves around proportion and lost favorites from do-not-wear lists of decades past. Pants with classic, fuller cuts, shirts that have room to layer, tuck, and drape, accessories once phased out. Imagine the British countryside aesthetic colliding with the ‘90s J.Crew catalog. The result: modern, fuller silhouettes catch up to the last decade's grounding in refined minimalism.
These clothes make sense together, and not in a way that requires learning a new aesthetic. For many of us, it's one we grew up with, now through our contemporary lens.
The jeans and pants drape, shirts offer room for a little lunch, and jackets manage to frame you without making you look like a wedding photo from 1992. Nothing is baggy, but it all feels a little less precious, everything looks like it belongs to an adult who knows where his keys are.
No one here is chasing the new for its own sake. As the fits across menswear have loosened, we're invited to a reunion where lost favorites like pants labeled “classic fit,” chunkier-shaped footwear, braided belts, and yes, the prodigal son cargo pant are given a modern edit: shapes you’ve worn before, now with better company.
Sure, you might grumble that you’ve been there, done that, but isn’t that the point? The challenge is finding out how these old shapes fit the current version of you, who, let’s face it, knows a lot more about taste.
The Scotland Shoot
If autumn had a brand ambassador, it would be Scotland: beautiful scenery, cool air, and weather that asks for layers. This year’s Fall Getup Week was photographed on a road trip starting in Edinburgh and meandering through narrow country roads until we reached the edge of the world in the Isle of Skye.
The weather is uncooperative, the ground even less so, and that’s fall, the kind you actually get, not the one they sell on coffee mugs.
Day 1: The Look
We're setting the tone: start with a waxed jacket, a soft flannel in a “shadow plaid” (low contrast and the lines blend instead of punch), straight fit pants in your new favorite color, and boots actually made to wear.
The Waxed Canvas Jacket
There’s a reason people keep buying these. Waxed jackets have been in steady use since the late 1800s. Waxed canvas, for the uninitiated, is cotton that’s been coated in enough wax to repel both rain and unsolicited opinions. It creases, darkens, and looks better for it. They come in hip-length field jackets and shorter trucker style. See our full guide on men’s jacket styles.
Or go for a trucker-style jacket for a shorter, waist-length waxed canvas option.
Brushed Flannel Brown Plaid Shirt
If your idea of flannel involves grunge rock, a paper towel mascot, or beer pong, this is a correction. Vintage brown plaid and enough room between an undershirt for oxygen.
Charcoal Twill Straight-Leg 5 Pocket Trousers
What the heck is a 5 pocket pant? Well, they're jeans but they're not made out of denim, so not jeans. These? Twill with a flick of stretch. Straight-legged, mid-rise, dignified, easy. Charcoal anchors everything and refuses to clash, no matter how ambitious you get.
Brown Leather Boots with Some Heft
Mud? Fine. Meeting? Also fine.
The Bertucci A-2T Vintage: field-tested style that nods to WW2-issue watches, built for today. Explore how military history continues to shape modern fashion.
Accoutrements
Tying it all together.
Come back tomorrow for more Fall Getup Week
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