Fall Getup Week: What the First Cold Morning Calls For

A man wearing a fall outfit stands outdoors leaning against a wooden fence post in a rugged rural landscape with grassy fields, patches of ferns, and rocky terrain. He is wearing a dark jacket, gray pants, brown boots, and a black cap, looking off to the side with one hand in his pocket. A metal gate and steep cliffs are visible in the background under a cloudy, moody sky. a badge reads fall getup week in the corner
Fuller cuts, British countryside, and the return of 90s favorites. The week begins with a look made for the season’s first breath of cold air.

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.

1990s j.crew fall men styles
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.

A man stands against a plain white background wearing a black baseball cap, a dark utility jacket with multiple pockets, a brown plaid flannel shirt layered over a white t-shirt, dark gray jeans, and brown leather shoes. The outfit is categorized as “smart casual” on a style spectrum displayed at the top of the image, which ranges from casual to dressy with color swatches beneath. The logo “Primer” appears in red text at the bottom right.
A flat lay display of a men’s smart casual outfit arranged on a light gray background. The items include a black utility jacket with gold snap buttons and a green plaid lining, a black baseball cap, a brown plaid flannel shirt, a plain white t-shirt, a pair of dark gray jeans, a silver wristwatch with a black face, and dark brown leather lace-up boots.

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.

scotland landscape

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.

men's fall outfit with black jacket and brown plaid shirt

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.

close up of field watch

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.

fall outfit, english countryside

Come back tomorrow for more Fall Getup Week

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Andrew Snavely

Andrew founded Primer in 2008 and brings 15+ years of men's style expertise. Known for his practical, relatable approach to style and self-development, he has been a recognized speaker at conferences and has styled work for top brands. Off-duty, he loves photography & editing, and enjoys road trips with his dog, Leela. Raised in rural Pennsylvania, educated in DC, and living in LA for nearly 20 years, Andrew's diverse experiences shape the relatable and real-world advice that has helped millions through Primer. On Instagram: @andrewsnavely and @primermagazine.