Never Stop Learning, Vol III

Put in your time in a place like Chicago, and the city will eventually pay you back in full.

But what does it mean to be a “local,” anyway? I’d argue the bulk of it is having the natural urge to get out and discover the city’s latest and greatest, regardless of your tenure here.

As a lifelong Chicagoan, I’m still picking up new tricks for getting the most out of the city every day — whether it’s knowing where to go to properly kit out my crib or having a line on the best table around on which to enjoy a martini and steak dinner with clients.

Of course, it never hurts to look good doing it. Because no matter how dogged you are in keeping up with what’s new, some things will always be classic.

And nobody knows classic like our friends at GANT. Those OG American sportswear dons have been outfitting well-dressed men — my pops and grandpops included — since the ’50s, while paving the way for guys like you and me. 

So we took to the streets to showcase some of my favorite Chicago finds, the scoops I picked up from each and the top-shelf gear that carried me through in high style.

School’s in session — join me, whydontcha?

Go easy,

Michael Nolledo
Chicago Editor

INTERIOR DEFINE

THE SKINNY
A brick-and-mortar guideshop from an innovative furniture startup peddling high-minded, fully customizable sofas.

THE LEARNINGS

• Never settle for the status quo — every piece of furniture is made to order to your exact specifications, right down to the inch.
• The occasional nap? Crucial. If your space can afford it, elect for a sofa that’s more than 60” long (say, closer to a 86”-90”) and at least 30” deep.
• Furniture shopping is a visual art. Whether it’s a U-shaped sofa or a one-arm chaise lounge, in-person inspection helps you better visualize how it’ll look in your space.

THE LOOK

The Perfect Oxford Shirt
GANT Diamond G / $98.50

BUY HERE

BIGGS CIGAR EMPORIUM

THE SKINNY
A stately den of stogie antiquity housed in a converted 19th-century Gold Coast mansion.

THE LEARNINGS

• Don’t be afraid to kick back and relax in the downstairs lounge — you’ll be surprised what the drag and burn from an Arturo Fuente can do for your state of mind.
• They don’t make ‘em like they used to: $50 grants you full access to the rest of the historic 1870s manse, while a yearly membership comes with your own personal humidor.
• When you’ve got money to burn, you burn rare cigars. Ask about the “vintage humidor,” stocked with a surfeit of hand-rolled smokables that date back to the 1870s.

THE LOOK

Indigo Block Striped Pullover Shirt
GANT Rugger / $145

BUY HERE

TRUNK CLUB CHICAGO

THE SKINNY
The handsome clubhouse for the hometown menswear concern where ace stylists will pour you a dram, pick some quality duds and send you on your way looking dapper and all the wiser.

THE LEARNINGS

• When it comes to the choosin’, tell these folks what you like and then let them drive — expert help’s what you came for, after all.
• Have that drink — you’d be surprised how much it helps you relax and opens up the dialogue, and an open dialogue leads to a more stylish you.
• Don’t be afraid to step outside your comfort zone — one of the best things about working with a stylist is that they’ll choose things you wouldn’t for yourself, with compliment-inducing results.

THE LOOK

Birdie Madras Checked Fitted Shirt
GANT / $100

BUY HERE

MAPLE & ASH

THE SKINNY
Opulent wood-fired steakhouse where excess is encouraged and the steaks are as show-stopping as the space that surrounds you.

THE LEARNINGS

• Ask for a round table in what they call the “300s” — these tables are all next to windows and offer lovely views of the park and triangle. Prefer to see and be seen? Request a center table in the atrium.
• A gentleman should begin every meal with a martini — your “amuse booze” is a gin martini shaken tableside and strained into a martini glass.
• Leave the pretense at home — ordering the IDGAF (“I Don’t Give a F—”) means the chef’s custom tasting menu, where servers will keep bringing you food until you wave the white napkin.
• Order option #2: The 48-oz. Eisenhower — the house porterhouse — with a magnum of Corison “Kronos” Cabernet, Napa 2011. Go big or go home, right?

THE LOOK

Beach Striped Shirt
GANT / $135

BUY HERE

QUEEN MARY

THE SKINNY
A “sailor’s tavern” in one of Chicago’s most happenin’ neighborhoods with a throwback maritime feel and cocktails of Navy strength on the menu.

THE LEARNINGS

• Whether with a date or solo, cocktails are best enjoyed at the ends of the bar, where drinkers can anchor down for the duration.
• This stretch of Wicker Park might belong to the bro, but Queen Mary does not. Skip the flip-flops, gents.
• Expand thy drinking horizons — the Daily Grog is nothing like you’ll find anywhere else in the city — a constantly rotating rum punch with fortified wines, citrus and freshly ground spices.
• Know your drunk history: as far back as the early 1800s, salty seafaring chaps used a sliding scale of drunkenness: one sheet, or “a sheet in the wind’s eye,” meant tipsy. So, being “three sheets to the wind” means you’re at sea but not completely lost.

THE LOOK

Pockster Shirt
GANT Rugger / $100

BUY HERE

THE SPECIFICS