Start with something like these affordable, not skinny, not baggy khakis from Uniqlo ($40).

Tip: Spend $10 and get them hemmed to the proper length (so they hit at the middle of your ankle bone). Or if you DGAF (and your workplace is laid back), just cut them with scissors.

Champion reverse-weave crewneck sweatshirt, $54.

Calvin Klein denim trucker jacket, $99 (or better yet, find one at a thrift shop).

New Balance ML999MU sneakers, $84.

Timex Expedition Scout watch, $40.

Uniqlo Oxford Slim Fit shirt, $30.

Topman Corduroy Harrington Jacket, $95.

Bass Ethan penny loafer, $80.

J.Crew Heart pattern socks, $9.

Tip: If you're wearing loafers, people will see your socks, so it's worth thinking about the color and pattern. Or if it's warm, forget the socks.

Kamakura Tokyo Slim Fit cutaway collar shirt, $79.

H&M linen-blend blazer, $80.

1901 Lewiston wingtip, $100.

The Tie Bar silk knit tie, $25.

Tip: Check out our Basic Ass Guide to Men's Shirt Collars.

Gap clean chambray, $60.

J.Crew slim cotton-cashmere crewneck sweater, $65.

Vans Authentic sneakers, $45.

FairEnds flannel camp cap, $30.

Tip: Wear the chambray over the sweater rather than under for a look that's more workwear than prep.

Braindead war energy tee, $45.

Starter x UO athletic bomber jacket, $89.

UO vegan leather flask, $18.

Tip: The older you get, the smaller the graphics on your tee should be.