Outfit of the Week, featuring Trunk Club

When it comes to clothes, guys get a bad rap.

Sure, many men find shopping to be a painful experience – something to be endured, rather than enjoyed. Right up there with listening to your wife talk about the fight she had with her sister, or your girlfriend making you watch Parenthood

But while men’s distaste for shopping is often translated as an indifference towards clothes, or style, I know that’s not the case at all.

Now, I realize I’m preaching to the handsome, well-dressed choir here, but there are in fact, quite a few guys out there who care about how they look.

They want to find the best items for their wardrobe; they just don’t want to be bothered going out and looking for those items. Sift through a million pairs of jeans. Hit ten different stores to find the best blazer.

But the road to well-dressed doesn’t have to be paved with misery. Or food courts.

Trunk Club figured this out, and came up with a way for guys to dress better, easier, every day. 

The Chicago-based personal styling and delivery service helps guys discover clothes that are perfect for them without ever having to go shopping. Glory be.

How It Works:

When you sign up with the service, you’re assigned a personal stylist. Over the phone – or, for those in Chicago, over beers at the showroom’s 40-foot bar – the stylist quizzes you about your lifestyle, corporate culture, and personal tastes. From there, your stylist hand-selects a “trunk” of items based on what you need and want. You try everything on at home (no depressing retail store mirrors and lighting to deal with), and send back what you don’t want.  Now that’s a low-stress, non-shopping shopping experience.

{one of 17 “dressing areas” at Trunk Club HQ} 

I’m often reminded that one of the reasons I connect with you guys so well here on Style Girlfriend is because while many women would happily spend the better part of a day shopping for the perfect dress/shoes/jeans/etc, that actually sounds like torture to me. My personal Guantanamo is lost luggage and a three-story mall looming in front of me.

I’d much rather tell someone, “I’m looking for the perfect…” whatever, then have them show up a few days later and say, Here it is!

For me, that’s the shopping sweet spot – you provide the style and direction, someone else does the leg work in helping find you those clothes that make you look great and feel super confident.

{yep, there’s an app for that}

The In’s and Out’s

Pricing at Trunk Club is comparable with what you’ll find at more upscale department stores. Brands include Gant, Jack Spade, Theory, New England Shirt Company, J Brand, and life/after/denim. There’s no membership fee, and shipping is always free.

Sure, the clothes don’t go on sale, but you also don’t have to watch for said-sales. Drive to the store. Wait for a dressing room. Try things on. Feel miserable that said-things don’t fit. I don’t know what you feel your time is worth, but mine is worth more than the hassle involved in getting a closet full of clothes that fit me and my style perfectly.

Even better, once you have a good relationship with your stylist, all you need to do is give them a shout when you need something new. Like magic, it’ll appear on your doorstep a few days later.

This week’s best dressed Style Girlfriend reader will receive a $200 gift card to kick the tires on Trunk Club.

And of course, once you’ve taken their styling services out for a spin, I’ll want to see what you got!


You guys know the drill by now. Give us some confident (but not cocky!) smiles, a good head-to-toe shot of your look, and of course, the in’s and out’s of what you’re wearing. Where you got the different pieces, the occasion, what you were thinking when you had it on…the whole shebang. Get your pics in to megan (at) stylegirlfriend(dot) com by Thursday at 9am EST!

Tell me:

Have you used a personal shopper or stylist before? How’d it go?