Classic Style
0 Comments

The Undone Prep Look for Spring.

By: Jen Shoop

Preppy never really goes “out,” but I have been seeing a lot of its elements floating around this spring, especially in the “undone”/”borrowed from the boys” vibe of the carpenter and utility pants that have been trending.

Prep Style Spring 2026

IMAGES VIA

A few pieces to achieve the look:

01. Loose-fit utility or carpenter pants or boxer-style shorts — the concept falls between “I just slipped this on” and “I could have borrowed this from a cousin so it looks a tad oversized.” It’s easy, body-skimming, I-woke-up-like-this, androgynous energy. A few of my top picks:

THE LESET KYOTO PANTS

THE J. CREW LUNA PANTS

BOXER SHORTS FROM COMME SI

02. A sneakily refined handbag or leather wrist-watch — in an outfit that is otherwise undone, borrowed from the boys, etc, create some tension with one polished or structured element. I love these Hermes-inspired watches from March Hare — I own in black (use code MAGPIE20 for 20% off). The Real Real is also an epic place to stalk and buy pre-loved Hermes watches — I bought myself this exact style from Hermes over a decade ago and still love it; you can always replace the straps! I also have this in my cart from TheRealReal. How fun is that cornflower blue?! I’ve always loved this style. On the handbag front, try an Hermes-style tote like this (compare with the Hermes Garden Party) or something structured like this (monogrammable!) Pam Munson. Or, of course, go with a classic canvas LL Bean Boat and Tote, or an upgraded version with this Rue De Verneuil.

03. Button-downs, always. My favorites are the Sezane tomboy (more tailored fit — take your true size and start with the white or blue), the Frank and Eileen (more oversized fit — think Ina Garten or Martha Stewart gardening vies), this denim (the wash is 10/10), and this fashion-y oversized style (runs intentionally oversized).

04. A Ralph Lauren ballcap. The khaki is probably my favorite.

05. Boat shoes! The Miu Miu ones are pinnacle. Madewell has a great look for less, and Sperry are the gold standard.

06. Stripes on stripes on stripes. Striped pants like these or these or these; striped totes like this or this.

07. Sweaters: rollneck and/or oversized. I love the rollnecks from La Ligne, but you can get the look for less here, here, here; this fisherman sweater is also perfect (look for less here — go up a size for the slouchy look).

08. To keep the look fresh, fold in an unexpected shoe (the whole “wrong shoe” theory), like a trendy jelly (look for less here) or fisherman sandal (look for less here), or try a statement bag in on-trend bandana print.

Undone Prep – Everyday Style.

Preppy Street Style Spring 2026

DENIM SHIRT // WHITE SHORTS (LOOK FOR LESS HERE) // BOAT SHOES (LOOK FOR LESS HERE) // CALL IT BY YOUR NAME TOTE // VERY VINTAGE SALINGER

Preppy Street Style Spring 2026

POPLIN PANTS // ROLLNECK SWEATER (LOOK FOR LESS HERE OR HERE) // JELLY SANDALS (LOOK FOR LESS HERE) // RDV TOTE

Preppy Street Style Spring 2026

COMME SI SHORTS // JENNI KAYNE SWEATER (LOOK FOR LESS HERE) // RL CAP // FREDA SALVADOR FISHERMAN SANDALS (LOOK FOR LESS HERE)

P.S. Things to emphasize in a normal day.

P.P.S. The best niche specialty foods! (Comments are chock full of recs!)

P.P.P.S. Transitional knits to wear right now.

This post may contain affiliate links. If you make a purchase through the links above, I may receive compensation. Image via.

Subscribe
Notify of
guest

0 Comments
Inline Feedbacks
View all comments
Previous Article

Next Article