FOR HIM: Men’s store proprietors (from left) Lindsay McKay, Adam Beltzman, Brad Habansky, Phillip Williams, Ralph Fasano, and Jeff Worth

Compared with its urban brethren—New York City, Paris, and Milan—Chicago is the sartorial stepchild in the men’s fashion world. For a time, it seemed that most men in the Windy City preferred jeans, T-shirts, and baseball hats to tailored, form-fitting clothes, and would sooner see their beloved Bears lose to the Packers than go shopping.

Now the typical Chicago man knows that soap and water alone are not acceptable substitutes for shampoo and shaving cream but still won’t spend hours at Sephora looking for products. “Men are learning that not every guy who dresses well is a metrosexual,” says Adam Beltzman, the owner of Haberdash in Old Town. “Just because a guy is fashionable doesn’t mean he gets his back waxed every week.” “He likes change and likes to look good,” says Ralph Fasano of his typical male customer. “We’re finding that when men look good, they get rewarded.” Fasano, along with Jeff Worth, owns His Stuff in Andersonville.

The rise of boutiques in the city is also encouraging men to develop their personal styles. “As long as stores like these pop up, Chicago men’s fashion will continue to come into its own,” says Lindsay McKay, the owner of TK Men in Bucktown.

Although the typical Chicago man might not be likely to wear furry Gucci boots (hot off the Milan runway), boutiques in the city continue to offer fresh fall options for men who are style curious but cringe at words like “manscaping,” “manbag,” and “metrosexual.” (Trust us, we do, too.) When it comes to sorting through the trends shown on the major runways, these boutique owners have got your back—waxed or not.





“I’m attracted to stronger colors and pieces put together in
an effortless way.”
—Lindsay McKay, the owner of TK Men

“I respect a guy who has a personal sense of style and can rock it.”
—Adam Beltzman, the owner of Haberdash

“What I notice is the cut of the clothes. I will notice the way a man walks, the jauntiness, the sense of confidence. Clothes play such an important part in that.” —John Jones, an owner of George Greene

“It turns me on if somebody makes it his own as opposed to a generic, out-of-the-mall look.” —Jeff Worth, an owner of His Stuff

“I’ll notice a cool pair of jeans.”
—Brad Habansky, the owner of Guise


“Some guys will come in and ask, ‘What’s your most popular jean?’ We hate that question. Just because a jean is popular doesn’t mean it will look good on you.” —Phillip Williams, the manager of Haberdash

“Inappropriate, not properly shined shoes.” —John Jones

“If the clothes don’t fit right, guys can look ‘schlumpity.’” —Ralph Fasano, an owner of His Stuff

“True Religion jeans, Oakley sunglasses, concert T-shirts, embroidery on blazers and shirts.” —Brad Habansky



George Greene
49 East Oak Street

2217 North Halsted Street

1350 North Wells Street

His Stuff
5314 North Clark Street

TK Men
1909 West North Avenue


Louis Vuitton



Slim silhouettes will be the norm as menswear continues to be more formal this fall. Whether it’s a trim button-down shirt or a made-to-measure suit, anyone can look sharp wearing this style.

“Not so long ago, there was the emergence of the bespoke suit,” says John Jones, who, along with Edmund Paszylk and John Moran, owns George Greene
on Oak Street, the haute-couture heart of Chicago. Men like to understand the mechanics of the process. “I’m also seeing more guys wearing suits at night,” says Brad Habansky, the owner of Guise in Lincoln Park.

For fall, George Greene will offer tailored designs from Alexander McQueen, Yohji Yamamoto, and Kiton, while Hugo Boss Red Label and J. Lindeberg will line the shelves at His Stuff. Guise will carry selections from R.E.D. Valentino and Filippa K, and Haberdash will offer button-down shirts by Duncan Quinn. “They’re $250 shirts, but we can’t keep them in stock,” says the manager, Phillip Williams.

IN YOUR WARDROBE A made-to-measure suit is a joy for all occasions—the office, a wedding, or a drink at the newest hotspot.

Diesel Denim Gallery



Some designers are ignoring the inconvenient truth of global warming by offering chalet-chic items such as streamlined parkas, bright stripes, and sleek sunglasses. Taking cues from hunting lodges and hiking expeditions, other designers are producing elegant plaids and sturdy mountain boots. Flannel hasn’t looked this good since the Brawny man got his much-needed makeover.

“A lot of designers are going for an outdoorsy look—flannels and plaids that are tailored and sophisticated,” says Jeff Worth of His Stuff. “There’s also the chalet look—parkas, et cetera—but again very tailored.” At His Stuff, you’ll find robust pieces from Energie and CNC–Costume National.

For Guise, Brad Habansky is picking up on the rugged trend with pieces from Guilded Age. “I’m also doing more raw denim and straight-leg jeans,” he says. He’ll also carry a Helmut Lang parka. “They’re getting dressier,” he adds. “You can throw one on with a suit, which is good because of the Chicago weather.”

IN YOUR WARDROBE If a weekend at a cabin is your thing, try dark-wash jeans and a plaid jacket over a cashmere sweater.





Military details are really hitting the mark this season. And we’re not talking about army green or camouflage prints—think less Full Metal Jacket and more An Officer and a Gentleman, with slim coats and form-fitting sweaters and parkas with details such as epaulets, large collars, shiny buttons, and sharp belts. One thing is certain—this look is anything but standard-issue.

“Pea coats are always in style, but this time they’re a little trimmer, in much nicer fabrics,” says Adam Beltzman of Haberdash.

He and manager Phillip Williams are excited about an officer’s jacket for fall from John Varvatos and, from Theory, a military-style vest with sweater sleeves, as well as tailored shirts with epaulets and sweaters with elbow patches.

At Guise, Habansky will carry a military-style olive-green jacket from Guilded Age and will also focus on bomber jackets.

IN YOUR WARDROBE Think about investing in a belted officer’s coat in a fine wool and choose a subtle color like brown, black, olive green, or gray.

To up your gentleman quotient, throw the coat over any outfit with a sharp watch and a pair of polished leather shoes.

Kenneth Cole Reaction



The word “streetwear” used to evoke images
of torn denim and Chuck Taylor high-tops that had seen better days. But times are changing. Although Lindsay McKay, the owner of TK Men in Bucktown, steers clear of giving advice on trends, she has noticed one shift in menswear. “The only trend I’m seeing is that general streetwear is getting cleaner,” she says. “I’m not doing faded, ripped-up jeans anymore.” Back-to-basics denim is making
a comeback, as well as hooded sweatshirts and retro sneakers.

Biker-inspired jewelry for men will also be big, predicts John Jones of George Greene. “It has to be very masculine and extremely well made,” he says.
At TK Men, McKay is carrying Cassette, Endovanera, denim from the Chicago designer BYA, and hooded tops by Combhard made of wet-suit material. “Guys come to me for the funkier stuff,” she says. At George Greene, expect to find pieces from Y-3 and jewelry from Chrome Hearts, while at Haberdash, you’ll see hooded sweatshirts from Theory and retro sneakers from Converse by John Varvatos.

IN YOUR WARDROBE You can’t go wrong with a hooded black sweatshirt under a blazer for a cool, urban look.

Bottega Veneta

Burberry Prorsum