143: Flip-flop season is just getting started

How to wear Havaianas' $27 slim square flip-flops three ways.

I’ve been thinking lately about The Row’s summer collection, a gorgeous but also hilarious procession of suiting that includes ankle-length tailored coats, leather capes, and multiple pairs of elbow-length gloves. For its summer collection! In hindsight, it was prescient to bet on the apathy we’d have for the season and skip right to pre-fall.

It’s 100º this week, but for anyone who doubts me for dressing and shopping autumnally, I can tap my retractable pointer to Exhibit A: The Row SS23 and say, “See? It doesn’t matter what you have on as long as you wear it with flip-flops.”

Fall fashion’s virtue lies in its ability to carry contradictions well: differently weighted fabrics, say, or variable coverage levels. (The shorts-and-sweaters weeks are among the most expertly leveraged by my favorite dressers.) If this fall’s lookbooks and ecomm images are any indication, the oxymoronic styling of flip-flops and formal wear is going to become a major addition to that canon—this may well be the flip-floppiest fall to date.

The Row’s own thong sandals solve a million dressing woes in their own rite, but lately I’ve been bypassing all my own “nice” flops in favor of a pair of $27 Havaianas—the people’s choice shoe of the summer (especially in their classic, Brazilophillic form)—mine a slim-square red set (more sizing here).

The shoes’ “cheapness” and coloring enhance the tension that makes flops a great partner to tailoring in the first place. Quite literally underlined in bright red ink is a reminder that it may be Fashion, but it’s not that Serious, friends!

Havaianas Slim Square flip-flops, $27 $34 (more sizing here) / Uniqlo U trench coat (similar from Cos, $225) / Sundar Bay button-down, $75 $150 / Mark Kenly Domino Tan skirt (similar, $245) / bag made my Nir’s mom :) (similar from Gemsun, $270)

I realized after the fact that I’ve made this edit tough to shop—a lot of the pieces I’m wearing are older or sold out everywhere or even from brands that no longer exist. Such is the case with someone who keeps and wears good things for a very long time. This priestly look, though, is highly replicable—I myself replicated a version from that Row collection and I’ve tried to point out suitable lookalikes in the credits. The Cos coat is not only a ringer, but perhaps an improvement, which is not a qualifier I attach often to Uniqlo U.

Havaianas Slim Square flip-flops, $27 $34 (more sizing here) / Entireworld t-shirt (similar from Leset, $70) / Helmut Lang logo band pants, $395 / my father’s Seiko watch (similar, $140)

Dead casual, maybe even too much, but a valuable sketch of an outfit if only for myself to reference when I forget (as I often do), what to wear when I just need to leave the house already. The instinct is to overcompensate with accessories…but don’t. This is a time for minimalism, not Minimalism™. I found that my father’s modest Seiko wristwatch and some super simple silver hoops were enough. This is not usually the spirit I bring to dressing/this newsletter, but it turns out I, too, am capable of skepticism toward the material world, at least in the presence of the right pair of Havaianas.

Havaianas Slim Square flip-flops, $27 $34 (more sizing here) / Pleats Please button-down, $212 (similar in gray, $186, similar tunic, $180) / Pleats Pleats wide-leg pants (similar, $590, similar in black, $590) / vintage Bottega Veneta Intrecciato hobo bag (similar, $3,000)

If you’ve seen me around town wearing this on multiple occasions…yes you did. So far, I’ve worn this exact look to drop off tailoring, attend a birthday party at an Irish bar, coffee date in the neighborhood, and have dinner at Atomix. Across multiple days! Pleats Please is a code-switching chameleon that can read appropriate in whatever setting you put it in, even when paired with loud beachy thongs.

The Havaianas are just $27 on sale (and these even simpler ones are $7!), with their power deriving precisely from being considered “low brow,” but a few bonus options that might achieve similar, yet slightly varied, end-results: obligatory The Row red flip flops and The Row red ankle-wraps you’d surely cherish, solid leather wraparound sandals from A.Emery that are completely different but just SO good and well-priced, and these absolutely exquisite hand-crafted leather flip-flops from Cecchi De Rossi that look snatched straight out of a Roman Empire display at the Met.

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Photos by Deb Leal