From helping his little man fix a bow tie to teaching his teen to shave after the initial sprouting of whiskers, Dad is a boy’s first superhero and style archetype. So in honor of Father’s Day, we talk to three father-son duos while they shop at New York City stores about their shared fashion perspectives.

Keeping It Cool
Not only are Bernard Hardy, 51, former detective and founder of Interstate Security & Investigations Inc., and his best friend, son Brent Hardy, 22, partners in the same firm, but their banter is just as infectious as their comfortably cool sense of style. Juxtapositioning pieces, such as a camo-print button-down with preppy khakis or crisp jeans, showcases their fresh fashion sensibilities. Though the guys are a bit casual, that doesn’t mean they don’t dress to impress. “I think you’re born with a sense of class, and that should be reflected in your style,” notes Bernard. And Brooklyn Circus, in—where else?—Brooklyn, seemed like the ideal place for this duo’s shopping excursion. Because the store has clean tailored pieces and funkier, more highbrow urban gear, we knew the guys would feel right at home. “Brooklyn Circus was like walking into my closet, except everything had tags on it,” says Brent.

Made To Measure
Giants among men, these Brooklyn gents command attention. Standing at 6 feet 3 inches, Charles L. Coleman Sr., a 64-year-old budget director at Medgar Evers College, and his 6-foot-4-inch son, Charles F. Coleman Jr., a 33-year-old attorney, are both larger than life. Powerful, polished and poised, they expect the same from their wardrobe. The only issue is their stature; it’s difficult to find fashion-forward pieces in large sizes. “It’s hard to buy off-the-rack suits; they normally don’t fit well, so you have to find a really great tailor. That makes all the difference,” says Charles Jr.  The Colemans prefer custom tailoring, so we took them to Alton Lane Premium Custom Clothiers in Manhattan, which offers scanning technology to precisely fit shirts and suits. And whether picking out the perfect pocket squares or browsing the button-downs, this father and son found a new style retreat in the bespoke men’s shop.

Uptown Flair
Bronx natives James and Chase Stratford are fashion risk takers. James, a 27-year-old radio and TV personality, wasn’t afraid to step out in a bright denim jacket with a hot-pink watch and sky-blue kicks, while his son Chase, 3, was drawn to a wild bow tie. Urban chic with a little uptown edge is the perfect descriptor for this dynamic duo. So what better setting than the sneakerhead destination House of Hoops in Harlem for this footwear-obsessed pair? “Believe it or not, Chase is very vocal about his likes and dislikes in terms of fashion. Though his style mimics mine now, I look forward to his really evolving,” notes proud papa James.