The Obtainer - 10/17/25, Friday

Valet.
The Obtainer

Friday,
October 17th Edition

Cory Ohlendorf

This isn’t your dad’s prep. It’s a new balance of comfort, texture and timeless cool.

- Cory Ohlendorf, Editor in Chief ⋯ @coryohlendorf

 

What We’re Wearing

Modern Prep

In fashion, trends will come and go (and then come back around), but preppy style seems to have been in (one way or another) forever. And while the core tenants seem to stick around, the execution is what ebbs and flows. The preppy look bridges the gap between buttoned-up high society and sporty youthfulness.

But the version we're leaning into now is looser, lived-in and more textured: Think classic codes without the costume. The look should feel as though each piece has aged into the outfit—the blazer broken in just so, the shirt crisp but never stiff, the denim relaxed and worn-in with a little bit of history of its own. The vibe is preppy's spirit reinterpreted, not reenacted. In this fit, every piece has a job. The blazer grounds the look and offers warmth, the Oxford shirt keeps things clean and traditional, the zip mock and jeans add cool, casual ease, while the braided belt and bluchers close the loop in quiet style.

Your Modern Preppy Fit

Clockwise, from top left:

Oxford shirt,
$185 by J. Press

Cotton chino cap,
$55 by Polo Ralph Lauren

Heritage trap blazer,
$358 by Relwen

Portuguese terry quarter-zip,
$158 by Todd Snyder

Vintage 505 jean,
$36 by Levi’s Secondhand

Retro stripe socks,
$14 by American Trench

Camp sole blucher,
$249 by Quoddy

Braided leather belt,
$69.50 / $39.50 by J.Crew Factory

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Smart Buys

The sales and discounts our team is currently watching.

 

Nike’s Zoom Vomero 5 is a textured throwback sneaker that’s great for both the gym and casual settings. It pairs airy textiles with synthetic leather and plastic accents to create a complex upper that's easy to style.

$170 / $102.97
by Nike

 

If you want a stylish lightweight jacket for fall but you don’t want to invest too much, this one from UNIQLO is perfect. It’s got a design inspired by vintage workwear with a modern relaxed silhouette and comes in three shades.

$49.90 / $29.90
by UNIQLO

 

Wellen’s adventure shorts live up to their name because they’re ready for anything. The breathable perforated material is anti-microbial and comes with a moisture-wicking lining and plenty of secure pockets, too.

$88 / $35
by Wellen

 

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Highsnobiety