Advice

Gray Areas

What to wear with a non-traditionally colored pair of Grensons, creative sock strategies, and more of your style dilemmas, solved!


Every week (or so…) I try to tackle a few of your most pressing style dilemmas. Send yours to [email protected], and in the meantime, here’s the latest…

Board shorts are very popular at the beach with 20-something-year-old surfers. Are board shorts appropriate when over 40?
Board shorts are a wonderful thing. Especially if they’re trim fitting and hit above the knee—you know, the way they’re worn by actual surfers. But if you’re not riding the waves every weekend, you likely don’t need the thigh protection board shorts provide. In which case I’d recommend a pair of more classically proportioned trunks that can double as shorts. They’re stylish, practical, and classic. Look for them on Gilt MAN from brands like Onia, Parke & Ronen, and my personal favorite, Orlebar Brown.

How do I get creative with my socks?
The simplest, albeit least tasteful, way to do so would be to follow the lead of the late-‘80s-era Red Hot Chili Peppers. Or you could just trade in the same old navies, grays and browns for a pair with some color. If you’re really feeling adventurous (and you plan on wearing clothes along with your socks), you might even try a colorful pair that—gasp!—doesn’t match anything else you’re wearing. I’ve always been a fan of a colorful sock, partly because—unlike, say, a colorful necktie—you can flash it at your discretion: Cross your legs, or don’t. As for how to procure said hosiery, you’ve come to the right place. Hardly a week goes by without vividly-merchandised socks sale. For more sock-related reading, don’t miss Joshua David Stein’s argument for the genre in Gilt MAN Essential #13.

What kind of pants or jeans would you recommend to wear with Light Grey Grenson William Oxfords? Thank You!
Those Grensons (above) would be a fine counterpoint to a colorful pair of jeans in, say, red or yellow. And they’d also look great with a gray. But you know what’d really look sharp? White jeans. Tweet or Instagram us a pic at @giltman and let us know what you chose to do.

Do you have a style dilemma we can help solve? Drop us a line at [email protected] and we’ll do our best to include it an upcoming column.

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