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20 ways to be a gentleman

From bespoke suits to sophisticated coffee shops, we've found numerous ways for you embrace your inner gentleman

By Time Out Editors in association with Gentleman Jack |
Nicholas Joseph Custom Tailors
Photograph: Brendon Brown

When you think of the word “gentleman”, a couple of images immediately leap to mind. There’s the kind of guy who is always dressed in a tailored suit with a matching tie and who knows exactly how he likes his whiskey (two fingers, neat). Then, there’s the fellow who hits the gym every night after work and is an expert on every subject, from politics to prehistory. No matter which side of the fence you fall on, being a gentleman means embracing the style, substance and attitude of a simpler time. To help you become the most sophisticated version of yourself, we came up with 20 ways to be a gentleman in Chicago.

Things to do

Photos from a night out with Gentleman Jack

Time Out Chicago partnered with Gentleman Jack to throw a pair of classy parties at Highline Bar + Lounge and Reverie. Attendees were able to enjoy special Gentleman Jack cocktails while trying on Goorin Bros. hats, perusing neck accessories fromThe Tie Bar and getting lathered up by the folks at Maestro Shave. Take a look at photos of all the gentlemen (and women) who came out to party with us.

20 ways to be a gentleman

Goorin Bros. Hat Shop
Photograph courtesy of Goorin Bros.

Don’t get caught without a hat

If you’re searching for something stylish to cover your head, look no further than the Goorin Bros. Hat Shop. Whether you’re a gentleman who prefers bowlers, fedoras or flat caps, you’re sure to find something dashing at the company’s Wicker Park and Lakeview outposts. The Goorin family has been producing quality headwear for more than a century, first establishing a shop in 1895, maintaining a level of craftsmanship that’s worthy of a tip of your hat.

Maestro Shave
Photograph: Martha Williams

Get a straight razor shave

Few things are more relaxing than a hot shave, especially when you’re not the one holding the straight razor. Maestro Shave is well-known for its hot lather shea butter shaves, which feature hot towels and a splash of aftershave. The River North shop also offers men’s haircuts and beard trims, all administered by barbers who know a thing or two about helping gentlemen look their best.

The Tie Bar

Find a tie for every occasion

There’s no better way to complete a gentlemanly outfit than with a stylish tie. Fans of skinny ties, bow ties and regular old neckties will be satisfied with the selection at the Tie Bar, a Chicago-based retailer that offers quality neck accessories at affordable prices. You’ll be able to browse through ties of all sizes and colors at the Lincoln Park store, including a collection designed by Dwyane Wade.


Dress the part

You have better things to do than search through stores or browse online retailers looking for sharp new clothes. Thank goodness there’s Haberdash, a one stop shop for sophisticated gentlemen that offers a tailored selection of denim, accessories and shoes. Don’t worry about tracking down the perfect pair of Alden boots or an Eidos Napoli shirt—the good folks at Haberdash have gathered everything a well-dressed man could ask for.

Brooklyn Boulders Chicago
Photograph courtesy of Brooklyn Boulders

Climb to new heights

A gentleman is always overcoming obstacles, such as the sheer, grip-covered climbing walls housed within Brooklyn Boulders’ 25,000-square-foot Chicago facility. The West Loop fitness center offers climbing classes, a weight room and an “active collaborative workspace” where members can tackle projects while getting some exercise. For those looking to escape the treadmill grind and get a leg up on a new hobby, this is the place to start.

Photograph: Maddie Blecha

Sport a high-quality haircut

Every gentleman knows that his hair is one of the first things a person will notice about him, so it’s important to keep it looking good. With five locations around the city, Halo [For Men] is the type of salon that can provide you with a haircut that exudes confidence. Each appointment includes a complimentary beverage, a hand massage, a hot towel and a free touch-up within two weeks of your visit—why settle for anything less?


Maintain a sense of humor

A gentleman understands that a good sense of humor can conquer some of life’s biggest challengers. There’s no better place to hone your comedic chops than at the legendary Second City Training Center, which boasts alumni like Stephen Colbert, Tina Fey and Bill Murray. Even if you don’t harbor dreams of being on Saturday Night Live, taking an improv or writing class will enhance your ability to remain confident, collected and hilarious in any situation.

The Blues Jean Bar
Photograph: Brendon Brown

Wear jeans that fit

Finding the perfect pair of jeans can sometimes seem like a fruitless search riddled with ill-fitting pants. That’s not the case at the Blues Jean Bar, where a “jeantender” will set you up with designer denim that is perfectly suited to your body as well as your distinct sense of style. Throw out your old jeans and head to the Lincoln Park shop, where you can try on offerings from Asbury Park Denim, Fidelity and other premium brands fit for a gentleman.

Nicholas Joseph Custom Tailors
Photograph: Brendon Brown

Dress like you mean business

A handsome suit is a gentleman’s uniform, so you should always wear one that makes you look your best. Ordering a bespoke suit from Nicholas Joseph ensures that your shirt, jacket and pants are specially tailored to fit your body in all the right ways. An expert tailor will help you select fabrics and take measurements to ensure a perfect fit, creating a custom pattern that is kept on file so that you can order additional suits with ease.

The Shoe Hospital
Photograph: Martha Williams

Keep your shoes looking sharp

Any gentleman who lives in a bustling city like Chicago knows that scuffed shoes are just another hazard of his daily commute. Fortunately, the footwear experts at the Shoe Hospital are around to nurse your weathered loafers back to a healthy shine. Whether you need a quick polish or a complete resoling, the staff at this Monadnock Building shop will have you back in your favorite pair of shoes in no time.

Iwan Ries & Co
Photograph: Brendon Brown

Know your local tobacconist

If you’re the kind of gentleman who enjoys smoking a pipe or a fine cigar, you should familiarize yourself with Iwan Ries & Co. The Chicago-based store is the oldest family-owned tobacconist in the United States, dating back to 1857—just twenty years after the city of Chicago was officially incorporated. The Jewelers Row shop still offers a wide selection of tobacco, pipes and cigars as well as the only BYOB smoking lounge in the Loop.

Evgeny Karandaev

Stock up on cocktail supplies

Anyone can throw together a simple cocktail, but a gentleman's home bar is always stocked with the tools of the mixology trade. Before you begin crafting an old fashioned or a whiskey sour, make sure that you visit Una Mae's to stock up on jiggers, cocktail strainers and bar spoons. You can also pick up a stylish flask—perfect for the times when you need a little Gentleman Jack in your back pocket.

Field Museum of Natural History in Chicago, Illinois, USA. The Field Museum is named after Marshall Field and is a popular attraction for tourists and local residents.
Paul Velgos

Never stop learning

No matter how far you’ve advanced in the world, a gentleman’s thirst for knowledge is never sated. Chicago is filled with museums and cultural institutions that allow you to fill your brain with facts that will impress your friends and admirers. Take advantage of the of your proximity to city’s most noteworthy institutions by viewing masterpieces at the Art Institute or getting a history lesson at the Field Museum.

The Fifth Avenue Man  inside Saks Fifth Avenue Chicago.
Photograph: Bill Waldorf

Look great from head to toe

A sharp pair of shoes is a necessary part of every gentleman’s outfit, whether you’re walking to a lunch meeting or running to the gym. To browse one of the largest selections of men’s shoes in the Midwest, head to the sixth floor of Saks Fifth Avenue, which houses more than 500 styles of boots, sneakers and loafers. From Sorel boots to Salvatore Ferragamo high tops, the footwear options are virtually endless.

Photograph: Martha Williams

Always pick up the spare

Next to golf and billiards, there’s no more gentlemanly sport than ten-pin bowling. Located in a former Schlitz brew house, Southport Lanes is the last hand-set bowling alley in the city, offering four lanes where you can get strikes and pick up spares the old fashioned way. Everything is done by hand, from scoring to the ball return, so make sure to slip a few bills into the finger hole of a ball and tip your pinboy.

Intelligentsia Broadway Coffee Bar

Enjoy a strong cup of coffee

A great cup of coffee may not put hair on your chest, but it will exhibit a gentleman’s discerning tastes. Impress your date with a visit to Intelligentsia Coffee, the high-end Midwestern roaster that is at least partially responsible for the city’s caffeine craze. Each location utilizes the pour-over brewing method, so you can watch as your barista turns direct-trade coffee and espresso beans into a delicious beverage.

Logan Hardware Records in Logan Square
Photograph: Emily Madigan

Listen to great music

No matter how powerful your stereo system is, queuing up a Spotify playlist isn’t nearly as impressive as digging into a gentleman’s record collection. Logan Hardware is a great place to begin building your music library, whether you’re interested in trendy new bands or classic rock.  After you’ve made a purchase, head to the back of the store and show off your pinball skills in the hidden arcade.

Photograph: Jaclyn Elizabeth Rivas

Always have the time

Anyone can dig out their smartphone and give you the time, but a gentleman needs only to roll up his sleeve. If you’re in search of a quality timepiece, the Shinola store in Bucktown offers a variety of the Detroit manufacturer’s handmade watches, in addition to leather goods and bicycles. Each stylish watch comes with a lifetime warranty, so you can take comfort in knowing that your gears will always be turning.

Photograph: Donna Rickles

Take care of yourself

At the end of a rough week, a gentleman deserves an opportunity to lay down and relax. The experts at Sir Spa can help you unwind with a rejuvenating massage in place that caters to guys. Whether you choose the hot stone massage or a quick tune-up for your back, you’ll have access to a locker room and lounge where you can catch the game before a visit to the steam room.

Strictly Fit
Photograph: Marzena Abrahamik

Whip yourself into shape

Gym memberships can seem like a superfluous expense, but a true gentleman takes his physical fitness very seriously. You’ll find like-minded individuals, top of the line equipment and high-energy classes at these elite Chicago gyms, whether you’re cycling at Flywheel or lifting weights at Equinox. With options located all over the city, you’ll have no trouble settling on a new location for your daily workout.


GENTLEMAN JACK is a registered trademark. ©2012 Jack Daniel’s. Gentleman Jack Rare tennessee Whiskey Alcohol 40% by Volume (80 proof). Distilled and Bottled by Jack Daniel Distillery, Lynchburg, Tennessee.