Derrick Rose Does GQ

Be Aggressive!

Toss on a bright windbreaker just before you head out the door. It's the quickest way to invigorate a drab look with some much needed color.

Windbreaker, $64, by Toddland. T-shirt, $26, and sneakers, $65, by Adidas Originals. Jeans, $54, by Levi's.

Go For the Tie

You should know by now that a tie isn't just for the office guy. Try a windbreaker-tie combo, the badass version of dressy casual.

Windbreaker, $895, by Dolce & Gabbana. Shirt, $160, by S.K.U. Tie, $130, by Band of Outsiders. Khakis, $52, by Dockers.

Take Control
Don't be afraid to put your own stamp on the jacket—cinch the drawstring or push up the sleeves. Forearm ink optional.

Windbreaker, $550, by Burberry Sport. T-shirt, $135, by Y-3. Track pants, $65, by Adidas Originals.

Guard Yourself
Plenty of windbreakers come with a hood. Use it.

Windbreaker, $95, by 55DSL. Tank top, $170, by Y-3. Cords, $295, by Burberry. Watch by IWC.

Watch Your Feet
Just as you'd do with your business wardrobe, try matching the color of your kicks to the rest of your outfit.

Windbreaker, $75, and sneakers, $65 by Adidas Originals. Shirt, $435, by Michael Bastian. Track pants, $255, by Y-3. Watch by Movado.