Let’s face it; men don’t love shopping quite as much as the ladies. They may even dread or despise it. With that being said, I headed to Trunk Club Men’s Outfitters at 311 W. Superior to see what founder and CEO Brian Spaly had to say on the subject. Trunk Club makes it easy for guys to get great clothes and accessories without having to set foot in a department store.

Here’s how it works:

Step 1: Talk briefly with a Trunk Club Stylist either in person, or by Skype, email or phone. They’ll get to know more about your likes and dislikes, and help you find clothes that will suit your lifestyle.

Step 2: Receive a “trunk” full of outfits picked out just for you by your personal stylist from the Trunk Club inventory, usually within two days and shipping is free.

Step 3: Try all the clothes on to see what fits and what you like. You can even do a virtual fitting using Skype. If you have questions or comments about sizes and/or style, your personal stylist is just a phone call or email away.

Step 4: Return the items that you don’t want with the included return FedEx label. Yes, that’s right. Free shipping once again. You will only be billed for the clothes you keep.

Step 5: Request a new “trunk” of clothes anytime with the same risk-free deal.

Brian Spaly’s Tips & Advice:

When I first arrived at Trunk Club, Brian took me on a tour of the loft, showing me the fitting area, stylists and inventory. I was amazed at the amount of beautiful men’s clothing everywhere. We’re talking over $1 million worth of inventory from high-end unique brands like Earnest Sewn, Autumn Cashmere, Genetics, Jack Spade, Reporter and Adriano Goldschmied. After he explained how the personal styling/shopping works, we sat down and got to business.

Brian’s first and foremost piece of advice when it comes to style for men is to buy clothing that fits well. This tip was essentially the reason Spaly took an interest in the fashion industry to begin with. While at Stanford, he used to complain about his pants not fitting right, so his girlfriend at the time teasingly bought him a sewing machine to fix the problem. Little did he know this would lead to an entrepreneurial career in the fashion industry, first with retail clothing line Bonobos, and then on to the launching of Trunk Club here in Chicago.

Next tip? Make sure you match.

To some this may seem like a no-brainer, but you would be surprised how many guys out there just don’t match their clothes and accessories.

Once you find an outfit that fits well and matches, focus on the details. Pair clothes with great shoes and a belt, or in the winter add a scarf and a fun pair of socks. If you’re going out somewhere nice, try adding a blazer. These details make the whole look come together.

Brian says another thing to keep in mind is trying new things. Many guys have “go-to clothes and just stick with it, that’s boring. Nobody likes dull and boring.” He says style and shopping for new clothes shouldn’t be an obligation, but rather a joy. Point? Be open-minded.

To conclude the interview, I asked Brian if he had any “don’ts” a.k.a. men’s fashion faux pas. His response? “Skinny jeans. Unless you’re a rock star.”

For more information on Trunk Club or to set up an appointment, visit their website at www.trunkclub.com or call (312) 266-8700.

Samantha McCarthy

Samantha McCarthy

Samantha McCarthy
is an editor and freelance writer in downtown Chicago.