midweSTYLE: Old Watertower, Chicago

Seth and I went looking for a suit with our friend Oliver, who's visiting from Kansas City. We talked about life and love and happiness—ya know, much like the rest of us who are meandering through this twenty-something phase trying to find purpose. You would think finding a slim-fitting suit would be an easy task. However, we're trying to find one that isn't going to break the bank. Student loans and entry-level jobs don't help the situation, but you need a suit for the interview, son.

ABOUT THE LOOKS:
Oliver is decked out in all J.Crew except the 1901 saddle shoes by Nordstrom.

But, why ALL J.Crew?
Because J.Crew provides menswear apparel that is affordable, accessible and good-looking. That, and his house burned down a few months ago, forcing him to start his wardrobe over from scratch. J.Crew has played a large part in nailing the essentials.

It's still cold as hell (that doesn't make sense) in Chicago even as we are nearing the end of March. I wanted to be warm but still have some compartments to carry my wallet, keys, chapstick and iPhone.

But can't you just carry those items in your pants like a normal person, Jeff?
You think I can fit a dime in this size 28 selvedge denim, let alone a wallet? Please.

To keep warm, I decided to rock the Patagonia Down Sweater under my thrifted J.Crew utility jacket. A little pop of red under my utility jacket—you know I dig it.

Jeff (left): Khaki utility jacket (thrifted, $6.99) by J.Crew, extra-small; down sweater (retail, sale $150) by Patagonia, small; green and white striped oxford (eBay, $20) by Gitman Bros Vintage; "The Henley" dry selvedge 14-ounce 'Karabo' fabric (Standard Style, $198) by Baldwin Denim, size 28; blue and green repp crest tie (thrifted, $1); cheap sunglasses I found in my car one day stole from Seth; blue suede bucks (Nordstrom, sale $44) by 1901.

Oliver (right): Grey utility shirt, small slim; wool University coat, small; Timex vintage field army watch; plaited blue cardigan, medium; Oxbow madras spring tie; 484 raw slim selvedge denim—all by J.Crew. Clubmaster sunglasses by Rayban; "Saddle Up" oxfords (Nordstrom, $99) by 1901, size 9.5.

Photography by Seth Putnam.