20 ways to be a gentleman

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.