J.Press Thinks Anyone Can Be a Preppie

With its fall 2026 collection, the ivy institution is breathing new life into prep. Plus, more of the best menswear drops from this week.

September 14, 2026 11:24 am EDT
Man with a mustache wearing a plaid blazer, white shirt, dark tie with white figures, and a J. Press baseball cap.
J.Press is reinventing prep for the masses
J.Press

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With dozens, if not hundreds, of new apparel, footwear and accessory releases from our favorite brands to sort through, I’ve done the hard work and winnowed things down to the absolute need-to-know style, watch and grooming drops that you can’t afford to miss.

This week’s haul: J.Press drops its Fall/Winter 2026 collection during New York Fashion Week, British streetwear label YMC slide-ifies a Merrell icon. Gap drops a staple outerwear style at an ultra-affordable price point and more.


Menswear Drop Checklist


J.Press Dachshund Intarsia Knit Cotton Sweater
J.Press Dachshund Intarsia Knit Cotton Sweater

J.Press has long been derided as stuffy and out of touch. Does this Dachshund knit look out of touch to you?

YMC x Merrell Moab 2 Slide
YMC x Merrell Moab 2 Slide

I didn’t know I needed a pair of shaved-down, hairy suede Moab slides until now.

Abercrombie & Fitch Relaxed Pleated Chino
Abercrombie & Fitch Relaxed Pleated Chino

Pleated, roomy and under $100? That’s definitionally a staple.

GapStudio Herringbone Peacoat
GapStudio Herringbone Peacoat

GapStudio — Gap’s design-forward sub-label — has been quietly churning out all sorts of heat over the past few months, including this cropped, fall-ready peacoat in crunchy herringbone.

Paul Smith Loves Barbour Chelsea Wellingtons
Paul Smith Loves Barbour Chelsea Wellingtons

Paul Smith’s latest collaboration with Barbour includes some excellent waxed jackets… and some even better rain boots.

Paul Smith Just Rehauled Fall’s Most Mandatory Jacket
Sir Paul Smith is bringing his signature brand of fun to Barbour’s iconic waxed jackets
Todd Snyder Warren Sweater Polo
Todd Snyder Warren Sweater Polo

Leave it to Mr. Americana to reinvent the classic chevon stripe sweater.

Studio Nicholson Ravel Pant
Studio Nicholson Ravel Pant

The perfect workwear-meets-menswear pant to break you out of your fatigues fatigue.

Flint and Tinder Quality Goods Graphic T-Shirt
Flint and Tinder Quality Goods Graphic T-Shirt

Shockingly, this shirt is not Coyote vs. Acme merch. Still, it couldn’t have dropped at a better time.

Les Tien Heavyweight Raw Zip Hoodie
Les Tien Heavyweight Raw Zip Hoodie

What “butter yellow” was to summer is what “washed crimson” will be to fall.

J.Crew 1986 Plaid Barn Jacket
J.Crew 1986 Plaid Barn Jacket

Everybody and their mother is going to be rocking a barn coat this fall. Considerably less people are going to have the foresight to cop this sweet plaid version from J.Crew before it inevitably sells out.

Polo Ralph Lauren Owen Leather Chelsea Boots
Polo Ralph Lauren Owen Leather Chelsea Boots

Hybrid pants? No bueno. Hybrid Chelsea-roper boots? Now we’re talking.

Haven x Norda 003G+ Trail Shoe
Haven x Norda 003G+ Trail Shoe

Haven and Norda are back like they never left. The Canadian duo just released yet another season-defining pair of trail shoes (two, actually — the lace-forward 001 and 003G+) built to withstand the season’s wackiest conditions and designed to look sick as hell when you’re slurping your post-hike matcha.

Giorgio Armani Oversized Ribbed Silk-Blend Sweater
Giorgio Armani Oversized Ribbed Silk-Blend Sweater

A design so ’90s it could’ve been yanked straight from the feed of @myarmaniarchive.

L.L.Bean Mountain Classic Print Fleece Pullover
L.L.Bean Mountain Classic Print Fleece Pullover

You can keep your Patagonia snap necks — I’m living in L.L.Bean this fall.

Relwen Bi-Waffle Thermal Mock
Relwen Bi-Waffle Thermal Mock

Thermals are back. So are henleys. Relwen decided to combine ’em.

J.L-A.L. Shin Loafer
J.L-A.L. Shin Loafer

The Shin Loafers from London-based J.L-A.L. caught fire online last season, mostly on account of its unique, modularly overlayed vamp. Now, the footwear is back for F/W, with a neat, finished trim to boot.

Frizmworks Wool Half Pullover
Frizmworks Wool Half Pullover

An all-natural wool, ultra-soft half-zip pullover? Korean label Frizmworks is clearly set to give Patagonia a run for its money this fall.

Paolo Sandoval

Paolo Sandoval

Paolo Sandoval is Style Editor at InsideHook, having previously contributed to Valet Mag. An expert when it comes to vintage denim, soccer kits and tailoring, Paolo reports on style, grooming, wellness, menswear trends, celebrity, media and other pursuits tangential to looking and feeling like a million bucks, and is the voice behind the InsideHook fashion newsletter, The Stitch. You can reach him at psandoval@insidehook.com.
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