I was recently contacted by a marketing rep from a Chicago-based company called Trunk Club. She asked if I’d be interested in becoming a customer and reviewing their service.

I’ve heard of Trunk Club, but I don’t know anyone who’s actually tried it, so I decided to give it a go and document the experience here on The Modest Man.

After all, my mission is to help men 5’8? and under dress better, and to that end I’m always down for trying new things.

The service is free to try, so I didn’t receive any compensation or incentive to do this.

What Is Trunk Club?

Trunk Club’s mission is to make it easier for men to dress well, and they do this by sending customers a box of hand-picked clothes upon request. In a nutshell, it works like this:

Step 1: You sign up at trunkclub.com and fill out a brief survey about your sizes and style preferences.

Step 2: A personal stylist contacts you and asks more detailed questions (“What colors do you like?” “What brands fit you well?”).

Step 3: The same stylist handpicks some clothes, packs them up in a box and send them to your home or office.

Step 4: You try everything on, keep (and pay for) what you like and send the rest back in the same box for free.

Step 5: You leave feedback about each item so your stylist can continuously improve their selections.

Step 6. When you’re ready, you ask your stylist to send another trunk.

Put simply, you’re outsourcing the whole clothes shopping process. Your Trunk Club stylist is handling everything from brand selection to shipping and returns, and it’s what they do all day, everyday.

They earn a commission on everything you buy, so they want you to like the clothes that they pick. But they also have a salary, so they won’t pressure you into buying anything you don’t want.

Sounds pretty good, right? What’s the catch?

Well, let me just say right off the bat that I don’t think this is going to work out for me. I love the idea, but I foresee one major problem: