Category Archives: My Style

Creating the Perfect Leather Jacket Outfit

January 6, 2026

Filed Under : My Style

What I’m Wearing
Leather Jacket| Sweater Vest | Pleated Pants | Mary Jane Loafers

A leather jacket instantly adds edge, even when the rest of the outfit is doing the whole smart, structured, and slightly academic thing. I layered mine over a crisp dress shirt and a cropped argyle sweater vest, paired with pleated pants and Mary Jane loafers for a look that feels equal parts prep school and street style. It’s proof that styling a leather jacket doesn’t always have to give biker. Sometimes, it quietly whispers fashion knows exactly what it’s doing.

Until next time,

-Bryce Lennon

How to Style a Shacket for Winter

January 2, 2026

Filed Under : My Style

What I’m Wearing
Shacket| Henley | Pants | Cowboy Boots

A burgundy shacket is that perfect in-between layer that says “I tried CHILE,” without actually trying too hard though. Today, I styled mine with a classic henley tee, thrifted and upcycled tweed pants, and cowboy boots. It’s giving fall street style, a subtle Western moment, and proof that a burgundy shacket really can do all the heavy lifting. No emotional support jacket required, PERIOD!

Always,

-Bryce Lennon

Styling a Boxy Fit Polo Shirt

May 22, 2025

Filed Under : My Style

What I’m Wearing
Polo Shirt| Denim Shorts | Loafers

Styling a boxy fit polo shirt is all about balancing proportions and texture. Today, I paired mine with jorts and loafers for a relaxed yet elevated look that works for weekend outings.

Later,

-Bryce Lennon

The Best Way to Dress Down a Boxy Dress Shirt

May 19, 2025

Filed Under : My Style

What I’m Wearing
Dress Shirt| Shorts | Loafers

Looking for tips on how to style a cropped dress shirt? Try pairing it with athletic shorts, loafers, and visible socks for a fresh mix of polished and sporty vibes. This combo is perfect for those fashion forward days when comfort and edge go hand in hand.

Adios,

-Bryce Lennon