William Sullivan-Cooper was running errands along Michigan Avenue.

Is this a suit that you’re wearing?
It’s one of my favorite suits that I got last summer while working at a fashion PR company in London.

How do you glam up a suit?
The best way to look good in a suit is through well-fitted and tailored pieces.

How can a man look professional but creative at the same time?
A man can easily look professional and creative through his accessories—whether it be a tie-bar, cuff links, pocket square etc.

What’s your approach to socks, shoes and hems?
I like a high-cut trouser to showcase the sock and shoe, a look not every man can nor should pull off.

How do you like to accessorize?
I accessorize with pieces I love and feel like me.

—Interview and photo by Isa Giallorenzo