The Style Guy Solves Every Sneakerhead’s Biggest Problem

Illustration By Janne Ivonen

A more-festive-than-usual Mark Anthony Green on two shoe-related challenges, a classic book (gift idea!), and a monogrammed wallet (gift idea!)

I just bought my first pair of nice shoes. But now I'm afraid to scuff them, so I mostly keep them in the closet. Is it silly to save them for special occasions?
This speaks to a bigger issue: Do I wear my good shit, or do I save it because it's good? It's the Sneakerhead's Dilemma, and it's confounded philosophers for decades. There really isn't a right or wrong answer, just different outlooks. Here's mine: Wear them as much as possible. Nice shoes especially. They can take a beating without falling apart and more often than not look better with a few war wounds. And the more you wear something, the less the price tag hurts. Those $800 boots seem a lot less expensive when you wear them four times a week. Neither option is wrong. Just note, I'll be wearing my nice clothes while yours will be at home, collecting dust.

I need a book on style. Timeless stuff. Rules, some principles. A primer.
I swear on Fred Astaire's ghost that I've done my due diligence to find a less obvious answer. But right is right. And perfect is perfect. Alan Flusser's Style and the Man, first published in 1996, is still the best book for understanding the foundation of men's dressing.

My husband has huge feet, which makes buying shoes a huge problem. Everything we find in size 15 is really, really ugly. Where should he look that's not a big-and-tall store?
Look to the feet of basketball players. Thanks to those rakish giants, more and more designers are making the good stuff in size 14 and bigger. Check out Del Toro, a favorite of Russell Westbrook. Then try Balenciaga and Alden.

Lately I've seen people with pins and buttons on their denim jackets—sometimes even their blazers. I can't decide if it's cool or childish. What's your say?
I've seen it done in really cool ways (cue LeBron James's small pin at last year's ESPYs), and I've seen it look like the uniform at Chotchkie's in Office Space (cue Jennifer Aniston flipping the bird). Moral of the story: The look is only as childish as the buttons. No puns. No memes. Nothing that says, “Keep Calm and Carry On.” The more vintage, the better. And cap the flair at two or three pieces.

The Style Guy is in! Send questions to styleguy@GQ.com or @GQStyleGuy.

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