please advise

Ask Chris Black: I’m Beach Bound — What Shoes Do I Get That Aren’t Basic Sperrys?

Photo: Julien Boudet

If you’re looking for the most powerful hair dryer or the handiest chef’s knife, those things can be easy enough to find. Other objects of desire are a little more taste-based. What’s the next status water bottle or hand wash, for instance? If you have a burning question about the next fanny pack or Noah rugby shirt, Chris Black is here to answer it in a regular column.

Recommendations for a basic, casual boat shoe or loafer for beach vacations? Want something more unique than a Sperry or Quoddy but not a $1,000 streetwear monstrosity? More like a warm-weather equivalent of everyone’s (and my) beloved Blundstone boots and New Balance 990s?

This is an ODDLY specific question, so I am going to give you a few options.

Sperry, I’m afraid, is the OG of this game. If the regular styles are too boring for you, go with a pair that is a FUN HOUSE of color. These will have your Waspy friends dropping their Aperol Spritzes when you walk by.

Or, instead of boat shoes, I like espadrilles. They are timeless and durable. This blue-striped pair from Drake’s is handmade in Spain from breathable Oxford cloth, so your dogs won’t sweat in Cap Ferret. They have a proper rubber sole, so you can wear them to dinner if you need to.

Please stick with me here, but I think flip-flops — on holiday — are cool. A cheap pair ($18) of Havaianas in navy cannot be beaten on the sand. If those are too low rent for you, Hermès makes a pair. I wouldn’t try to raise a sail in them, but post-swim, they work. No muss, no fuss.

From $56

Maybe you are ready to try something … WILD. The Hydro Moc from outdoor-gear brand Merrell is an exciting shoe-sandal hybrid. Kanye ripped the style off, and they will give you wild foot tan lines, but I am weirdly attracted to them.

Finally, I must also recommend my J.M. Weston loafers, which I’ve worn on vacation before. Yes, they cost about as much as a $1,000 streetwear monstrosity — but, unlike trendier footwear, these are classics that won’t go out of style. To that end, they look chic anywhere, and a little sand can be brushed right off.

Warby Parker used to sell frames called “Abbot,” and they were perfect for my slim, Scandinavian face. Now I need a new prescription, and it no longer sells that particular frame. Any suggestions for something similar? Preferably, something that comes in white/clear.

Time to upgrade, friend.

If you must stay on the lower end price-wise, the Waylaid from Eyebobs in crystal would be a slight departure but probably still flattering. They are a little meatier but won’t overpower those slim Scandi features!

This style from progressive Japanese brand Matsuda is going to cost you a lot more, but they have a similar look and are undoubtedly better quality.

Less expensive (by about a hundred bucks) is the Zev-TT frame from Moscot, which is a good option as well. It only comes in gold, but I feel like you could pull it off. This is probably the style Warby Parker ripped off, LOL.

Saw you were just at Pitti Uomo. Are the fashion folk carrying any new status items or accessories I should know about?

Most of the things I saw at Pitti Uomo … were awful. Although I was distracted by delicious carbohydrates at every turn, I was able to capture a few cool guys, and, yes, I did spot some trends!

I saw a lot of the color green, which I like. This got me looking at other cool green stuff. These tonal patchwork Army trousers from Folk are very cool and well priced. We love a statement pant!

From $58

When the weather permits wearing one, nothing is more classic than a pique Lacoste polo. This one in deep green is perfect for some afternoon clay-court action!

This insane PVC tote bag from Bode is speaking to me. The trim is a green corduroy that compliments the vintage “inset graphic appliqués” — this is a show-stopper. Fill it up with your personal effects and prepare to be applauded!

The Strategist is designed to surface the most useful, expert recommendations for things to buy across the vast e-commerce landscape. Some of our latest conquests include the best acne treatments, rolling luggage, pillows for side sleepers, natural anxiety remedies, and bath towels. We update links when possible, but note that deals can expire and all prices are subject to change.

Ask Chris: I’m Beach Bound. What Non-Sperry Shoes Do I Get?