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

How to Make the Oversized Blazer Trend Work for You

May 17, 2025

Filed Under : My Style

What I’m Wearing
Soccer Shorts| Sweatshirts| Sneakers

Wondering how to style an oversized blazer as a man? Pair it with a cropped tank, high-waisted barrel jeans, and loafers for a bold, fashion-forward look that blends structure with street style.

That’s all I got for you,

-Bryce Lennon