The Obtainer - 10/17/25, Friday
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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,J. Press
$185 byCotton chino cap,Polo Ralph Lauren
$55 byHeritage trap blazer,Relwen
$358 byPortuguese terry quarter-zip,Todd Snyder
$158 byVintage 505 jean,Levi’s Secondhand
$36 byRetro stripe socks,American Trench
$14 byCamp sole blucher,Quoddy
$249 byBraided leather belt,$69.50 / $39.50 by J.Crew Factory
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![]() 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.
| ![]() 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.
| ![]() 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.
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