1. The Franklin Room

This River North speakeasy (pictured) is serious about whiskey, with an exceptional collection of rare releases and covetable bottles. If you find one you like, buy the bottle, drink what you want, and the bartender will store it under lock and key. Trust us: You’ll look cool when you return with your friends and ask the server to fetch your bottle. Bottles from $270. 675 N. Franklin St., franklinroom.com

2. Yearbook

There’s just something appealingly roguish about toting a flask—remember when George Clooney was seen sipping from one at the Oscars a few years back? This interior design firm’s shop sells flasks in stainless steel, chrome, and pewter, plus a few encased in leather. We love the ones engraved with an English bulldog. From $26. 7316 W. Madison St., Forest Park, yearbookstudios.com

3. ESQ Clothing

Since you get to choose from some 45,000 English and Italian fabrics at this custom clothier, there’s only a 0.00045 percent likelihood you’ll show up wearing the same suit as your pal. Bonus: bragging rights that you share a tailor with Chance the Rapper. (An ultraviolet jacket and trousers like these go for $5,650.) 555 W. Jackson Blvd., esqclothing.com

4. J. Toor

Men’s clothes can be fun, too, you know. This gorgeous Mag Mile store offers impeccable off-the-rack and bespoke styles (like this crisp French-cuffed number, $220) with a British sensibility in any color or combination of colors you want. 900 N. Michigan Ave., jtoor.com

5. Richard’s Fabulous Finds

This isn’t the mildewy vintage shop from your college days. The thoughtfully curated men’s accessories here (like these tiger-eye cufflinks, $49) run the style gamut from F. Scott Fitzgerald to Curtis Mayfield. 2545 W. North Ave., richardsfabulousfinds.com

Changes to This Story

• July 18, 2017: An earlier version of this story said the location is Streeterville. The Franklin Room is in River North.