Rugged Meets Preppy

Spring is in full swing. Breezy mornings, warm afternoons, plenty of sunshine — and people are feeling the buzz. So is our guy Jesse, out on his daily commute.

Jesse rarely takes a day off. Whether it’s work, school, parties, or festivals, he’s always in the mix. And speaking of mixing things up, Jesse’s not afraid to blend styles — that comes through clearly in his latest staff pick.

—“To start off, I love Spring. The longer days, the perfect weather — it’s the best time to get creative with layers and mix up styles. This season, I’ve gone for a look that merges two concepts: preppy Ivy style and rugged workwear.

The Carhartt WIP Single Knee Shorts are a breezy take on a classic workwear piece. Paired with the matching Lincoln Shirt Jacket, they form a solid, no-nonsense base, tough, reliable, and ready for action. To contrast the ruggedness, I’ve added the Jays by Vagabond. These deck shoes have a polished, preppy feel that complements the earthy tones of the outfit. Keeping that elevated edge, the Wood Wood Day Gingham shirt adds a soft, warm tone that ties the look together. It’s dressy, but relaxed, perfect for Spring.

To finish it off, I’ve gone with the Dax sunglasses by Komono. The modern shape and brown frames balance the whole outfit, from top to bottom. And the Topologie bag with its multi-compartment strap? It’s the subtle cherry on top, stylish and seriously practical.”

Let us know what you think of Jesse’s Spring-ready mix and come through to shop the full look.