Trunk Club

For guys who don't have a lot of time on their hands or perhaps those who don't particularly enjoy shopping, Trunk Club offers a modern solution with some old fashioned service. After a quick chat about your size and style preferences, a personal stylist will assemble what might work best for you and FedEx it straight to your door. No algorithms or warehouse robots, but a real live person who understands which brands and styles will fit you best.

There's no membership fees or minimum orders (you can request full outfits or simply a range of shirts if you want). And there are no commitments. Trunk Club pays for shipping both ways, and you'll have 10 days to try everything on in the comfort of your home and see what works for you. Don't like an item? Simply use the prepaid label to return whatever didn't make the cut—you'll only pay for what you keep. And with each order, your stylist gets to know your personal preferences, which makes for better trunks when you're in need of something new. What's more, they're stocking some of the best menswear brands on the market today, from Eton, Gant Rugger and D.S. Dundee to Oak Street Bootmakers and Jack Spade.

We asked Jason Smith, Trunk Club's VP of product, to assemble a trunk of essentials for Memorial Day weekend. "This selection showcases what a new Trunk Club member can expect from his first-time trunk: between 6-8 hand-selected wardrobe staples that will quickly become the most popular items in his closet," says Smith. "I figured this guy already has the basics covered, so I wanted to focus on the following key pieces—which will provide a ton of use over the course of the summer."

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  In Chicago?: Stop by Trunk Club's kitted-out loft in Chicago's River North neighborhood, complete with a stocked bar and a team of stylists and tailors to take care of you.

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