Does Your Guy Know How To Dress?

He might have a dreamy smile. His eyes could be the color of a deep blue ocean. And his witty, funny sense of humor might be what you fall in love with over and over again. But, when it comes to the clothes on his body, does your guy know what he’s doing?

Does your guy know how to dress?

A good dresser might make an otherwise average looking guy look fantastic. On the flipside, an extremely handsome man who is clueless when it comes to dressing might ruin his good looks with the clothes he chooses to wear around town.

Lynn Bruno is a Chicago-based style advisor for J. Hilburn Men’s Custom Clothier. “What guy loves to shop? NONE!” she says, “But most of them want to look their best.” Bruno says that’s why a man might need his girlfriend’s or his wife’s help.

“Maybe start with looking through his magazines like GQ, Men’s Health, Esquire, etc and asking his opinion on certain looks, colors, or styles. I always ask my husband, ‘What do you think of this?’ just to gage his interest in something.”

I asked Lynn, “What are some of the biggest dressing mistakes men make?”

“They wear big, blousy dress shirts, they wear boring dress shirts (all white or all blue), they wear suits that look ‘boxy,’ and they wear baggy trousers.”

And what if a guy has a big belly? How can he hide it? Lynn suggests custom clothing.

“The key is not necessarily to ‘hide’ their flaws, but just fit them properly. Custom dress shirts or custom sport coats are made to their exact measurements, so the clothing conforms to their bodies instead of adding bulk and extra fabric. We’re not talking tight clothing….it will still give them several inches on either side of the torso for movement. I have several larger customers who are thrilled to have a dress shirt that fits around their waist, but then also fits them in spots where they are more normal sized. These guys would typically have to go up to a 2XL just to fit their waist, but then are stuck with a baggy garment everywhere else.”

Bruno says despite all the guys who are clothing nightmares, she also sees lots of men who dress really nicely.

“A well dressed man has a classic style with a modern twist. His classic cut suit fits him perfectly with modern details like maybe a narrower lapel, or an added ticket pocket. He pays attention to details like adding a pocket square or a crocodile belt. When he takes off his suit coat, his shirt doesn’t spill out over the edges of his trousers. It is not tight, but tapers in toward his waist. His trousers are flat front, and are hemmed to the correct length. His tie is bold and tied correctly. His shoes are polished.”

According to Bruno, the way to get your guy to make the switch to custom clothing is to try just one custom shirt or one custom pair of pants.

“When they see how amazing they look in their well-fitting clothing, they typically don’t ever go back to buying off-the-rack clothing again.”

To get more tips and to learn more about J. Hillburn, visit

Jackie Pilossoph

Jackie Pilossoph is the author of FREE GIFT WITH PURCHASE and two other novels. She is also a freelance magazine writer and weekly newspaper columnist. Pilossoph holds a Masters degree in Communication from Boston University. She lives in Chicago and is working on her fourth novel.