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How Can I Get My Boyfriend To Ditch His Chucks and Grow Up?

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Racked is no longer publishing. Thank you to everyone who read our work over the years. The archives will remain available here; for new stories, head over to Vox.com, where our staff is covering consumer culture for The Goods by Vox. You can also see what we’re up to by signing up here.

Love, Frank has returned as a weekly style advice column. Addressing a different reader's fashion glitch each and every week, it will tackle all the hard-hitting issues—like whether or not you can wear white to a wedding and where to find cute shoelaces. Today's question:

Dear Frank,

My boyfriend's shoe game needs help. Here's the short version: he's getting older, but his shoes have stayed the same. As he creeps closer to 30, sneakers look more and more juvenile on him, but he doesn't work anywhere stuffy enough to necessitate dress shoes. What's his next (pun intended) step?

Love,
Formerly Mrs. Chuck Taylor

If only. Via J.Crew

Dear Mrs. Taylor,

As a guy who wears some pretty juvenile footwear—classic black and white checkerboard Vans slip-ons as I type—I'm not sure I would consider canvas sneakers on professional adults as a fashion faux pas. In fact, I find it kind of charming; and I wholeheartedly believe everybody should have a classic pair of Converse—or Vans, or Keds, whichever canvas of choice—in their shoe arsenal. That said, I could be in total denial. Or, perhaps a bit more likely, I get a pass because I also own brogues, oxfords, desert boots, penny loafers, boat shoes, wingtips, combat boots, and Common Projects.

But here's the thing—a lot of guys really identify with that canvas sneaker. That Chuck Taylor is more than the some of its parts. It represents youth; its a reminder of smoking cigarettes in the woods after school and hearing Pavement for the first time and all-ages shows in church basements. It's sort of a way of saying, "Hey, I'm still sort of young-ish and a little bit with it." Converse All-Stars are the vestiges of hip and young—for men who can no longer necessarily claim either.

Plus, those classic kicks are just really easy: Comfortable enough, cheap, they match everything. Why fix something that isn't broken? Well, because 30.

DIY Converse

A 30-year-old needs more than a pair of Vans. This doesn't mean he can't up his footwear game with Vans. Have him try on classic lace-ups in tonal black or white. Better yet, these leather options can be dressed up or down—they look great with almost anything. Likewise, Chuck Taylors come in tonal and leather iterations—colors ranging from white to day-to-night-appropriate burgundy or indigo. I'm also crazy about the custom Converse options on-line—where you can dress up that sneaker with tonal soles or contrast stitching, even a monogram.

One step further, the Jack Purcell style by Converse is a little less basement rock show, a little preppier, a little cleaner. A pair of those to replace a worn out Chuck might be a good start. Another option is an ultra-chic, super clean pair of Italian-made, virtually unbranded sneaker hybrids by the aforementioned Common Projects. These are sneakers, but barely, and can be worn with anything. Yes, they're a bit pricey, but they last. Your other option? Faux-Common Projects: Try All Saints or Creative Recreation.

All said, one can't just wear sneakers. Nor does one necessarily need a true dress shoe for every day. A good compromise is a casual shoe in leather or suede. If you're looking for a bargain, Bass makes a plethora of American classics that are anything but stuffy or overly adult. Their Weejuns penny loafer is a cornerstone of prepdom and is now available in a range of color combinations. They also make a great boat shoe, an inherently wearable buck, and fun saddle shoes with varied levels of color-combining quirkiness.

Another un-intimidating place to start is at the Clarks store in your mall. There, a dress-shoe-phobic guy can pick up a plethora of casual, comfortable options that are a relative bargain. A desert boot can be paired with anything—even shorts. They also offer that classic Wallabee style. A little fusty and certainly not for everyone, Wallabees sort of evoke an anti-chic, indie rock indifference that you can use as a selling point: "These will look great with your corduroys, honey!"

Furry, camo-print Sperrys

And we can't forget Sperry. Who can't wear a boat shoe? They're even less of a dress shoe than a canvas slip-on. They're easy to find and they come in every color and every fabrication with every contrast color and contrast fabrication. Now you can even order him a pair of exclusives by Jeffrey. There are boat shoe and slip-on styles in snakeskin, ponyhair, camo—all kinds of fun stuff.

A last/best resort: J.Crew. Now that the once-marmish catalog brand is essentially a lifestyle department store for the hip-tinged preps amongst us (a.k.a. everyone), they stock wares from all sorts of other brands. That includes men's footwear. And if J.Crew is stocking a shoe, you know it's wearable and unfussy and in demand (or, well, about to be). Let him loose, he'll find something.

And take note: J.Crew stocks a bunch of retro canvas sneakers—Vans included. If The Crew says a real man can wear a canvas sneaker (at least on occasion), who are you to judge?

Got a style question for Frank? Leave it in the comments or email one in here. Then buckle your two-toned leather Moschino belts, folks, because it's going to be ? Something.
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