The end of summer always sneaks up. One day you’re sweating through tees, the next you’re grabbing a layer for that chill in the air. That’s why I pulled together a few of my go-to pairings that’ll get you through this weird in-between season and beyond.
1. The Popover/ Long Sleeve Shirt + Shorts Combo
When it’s not quite flannel weather, but you don’t want to look like you’re clinging to July — this is the move. A popover or long sleeve woven shirt up top keeps things refined, while rugged canvas shorts ground it in utility. It’s laid-back, clean, and ready for everything from casual Friday to happy hour.
Build The Look: Offsides Popover + Beige Cotton Linen Field Shorts + Flower Mountain Iwano 2 Suede Sneakers
2. Denim That Works Double-Time
This is the season for jeans that can go either way — cuff ’em with loafers on warmer days, or throw on sneakers when the chill sets in. Kato’s denim breaks in like an old mitt, but still looks sharp enough for work or a night out.
Build the look: Kato Slim Selvedge Denim + Flower Mountain Iwano 2 Suede Sneakers + Olive Seersucker Camp Collar
3. The Overshirt & Chore Coat = Your Secret Weapon
This is my #1 move when the weather can’t make up its mind. Toss it on over a tee or Henley in the morning, keep it handy for patio beers after work. Built rugged but refined — this is the layer you’ll reach for more than anything else.
Build the look: Black Ripstop Overshirt + Black Ripstop Utility Shorts + Astorflex Suede Loafer
4. Accessories That Do Work
Sometimes it’s the small details that pull it all together. A belt that’ll last decades. A hat that feels sporty and not like a throwaway. Pieces that round out the look without overthinking it.
Build the look: Elk Head Chain Stitch Hat + Classic Leather Belt + Q Timex Green Reissued Watch
The Wrap-Up
Fall’s about balance — sporty but refined. These are the pieces I’ll be living in while the seasons duke it out. Check out the full collection and build your own transition lineup.