Art by Lia Kantrowitz.

How To Dress Like a Wealthy Widow on Holiday In The Mediterranean

It's entirely possible to make your late-summer wardrobe scream "poolside elegance" without a late spouse's financial assistance.

Jul 30 2018, 7:16pm

Art by Lia Kantrowitz.

Welcome to Luxury Rules, a new life and style column for people of taste who are also on a budget. For our first edition, her royal flyness Dodai Stewart ensures that the rest of your summer wardrobe will be dress code–appropriate for a tragic yacht "accident" off the coast of Malta (or, you know, wherever it is you're going).

Hi hi hi! Dodai here. You may know me as a writer, editor, and future Oscar-winning screenwriter, but you may not know that I identify as a bon vivant, sybarite, and voluptuary, meaning I aspire to perfect the art of living well.

Take note: Enjoying life’s pleasures does not always mean spending a lot of cash. If you’re like me, you’ve got caviar tastes and a fishstick budget. And yet: You dream of effortless cool. Of floating ethereally through the crowds at the beach, your presence rendering the riffraff so gobsmacked that they instinctively part like the Red Sea for Moses. Or perhaps you’re headed poolside, and hope to be so dazzling that friends, family members, and cabana boys get distracted, trip, and fall gaspingly into the deep end.

You only need a few things to turn these fantasies into a reality, and you don’t need to take out a loan—almost every item here is under $100. Ready to dress like a diva on a dime? Let’s begin.


GIF of Overboard via GIPHY.

Celebrities may be dabbling in the tiny-sunglasses trend, but let’s be real: The truly wealthy don’t make eye contact with plebs, and oversized shades never go out of style. It helps if you choose a pair with crystals so that you are able to blind your enemies from a distance if necessary.

Should you have the means, opt for a famous Italian luxury brand’s star-spangled sunnies (rhymes with Smoochie), but just know: these large crystal-studded frames are cheap, eye-catchingly glam, and big enough to hide the tears you’re shedding over your poor late husband Giacomo. Or Reza, or whatever.


Photo by Anthony Barboza/Getty Images.

Cutoff shorts and tank tops are fine, especially if you’re operating a charity car wash or have brothers on the run from Boss Hogg. But if you’d like to level up to wealthy widow status while keeping cool, you need to build a caftan wardrobe. Breezy, billowy, deceptively simple way to get dressed. If it’s good enough for Liz Taylor and 67 percent of folks in Marrakech*, it’s good enough for you.

I’m partial to these $30 numbers from Moroccan Caftans— I have a blue and an orange. Just the thing for waking up, watching the sun rise, and contemplating whether or not you should take the cabana boy as your lover.

* Not factually accurate.


Photo by Keystone/Hulton Archive/Getty Images.

Truly living in luxury means never having to unbutton your jeans after dinner. And since your third marriage ended with Massimo mysteriously falling overboard somewhere near Malta, never to be seen again, you’re eating for two. As in: him and you. Poor thing—he really loved prawns!

Get one in a dark color with sequins or sequins or embellishments. Live your best life.


Carmen Miranda. Photo by NBC/NBCU Photo Bank via Getty Images.

Glamor is never subtle. You need eye-catching, dramatic, spectacular. The better to catch the glints of the sun setting over the Aegean. Think pearl-encrusted Helena Christensen in vintage Chanel ads. Think Rihanna in chunky gold links. Think Anjelica Huston as Eleanor Zissou in The Life Aquatic. And be advised: This look isn’t just for poolside play or yawning on a yacht: Giant necklaces make even the most basic ensembles better: Think Beyoncé in Formation. Think Diana Trout in Younger. Think, again: What Would Liz Taylor Do!

This Beyoncé-esque number is cute. That said, don’t be afraid to GO BIG—I also love this extremely not-subtle piece that makes an actual statement. Just, as they say, do it. Your ex, the viscount, may be dead, but today is the first day of the rest of your life.


Faye Dunaway. Photo by Terry O'Neill/Iconic Images/Getty Images.

On Miss Fisher’s Murder Mysteries, Downton Abbey, or in regency romance novels, one dresses to stay in just as carefully as one dresses to go out. In fact: One of the best things you can do for yourself is acquire a pretty robe. Just one piece turns schlubby lounging into a lavish affair. Coming home and taking off your pants (and bra!) but still being covered enough for the Chinese food delivery guy is a key to living well.

Cotton yukatas are comfortable and washable, but should you feel the need to splurge on a silk one, a sheer tulle feathery number, or a custom design, it’s completely understandable, since you’ll quickly find you’ll end up wearing it every day. Pro-tip: the thicker, more structured the fabric, the more “forgiving” it will be for a lady trying to cover up. Slinky and silky = not as easy to be naked underneath. You’ll want to be somewhat modest when the authorities arrive to question you.


Elizabeth Taylor. Photo by Ron Galella/WireImage via Getty Images.

Whomstever created that erroneous accessory rule “take one thing off” never watched any 1980s rich-bitch TV? Or The Simple Life? Or saw any photographs of Mae West???? Or Josephine Baker?

Doesn’t matter if you’re engaged, plan to be engaged, or avoid commitments at all costs: Get yourself a gigantic ring. A cocktail ring, meaning big enough to flash while you’re sipping spirits. My favorite one came from a local party favor store. For all anyone knows, it’s an heirloom and your late great husband wanted you to have it. And if someone says “Goodness, what a beautiful diamond,” you can copy Ms. West and reply, “Goodness had nothing to do with it.” $5,; $29, IzaBelaJewels.


Photo by Victor Boyko/Getty Images for IMG.

It’s dangerous going from ship to shore, darling. Let the other silly things teeter and wobble and mince about on high heels—you’re on your third husband and fourth mimosa, so flats are where it’s at. Pro tip: Don’t pick shoes with soles that are too hard or inflexible, or your feet will hurt. Cushioned insoles are even better. All you really need is a little shine! Channel Wonder Woman Gal Godot’s golden gladiator-inspired sandals, or try a jeweled sandal: $40,, shimmery Havaianas flip flops, $50, or $28 glittery Reef Stargazers, $90 micro-wedges from Talbots, $115 rhinestone sandals from Soft Surroundings.


Lupita Nyong'o. Photo by Jeff Spicer/Getty Images for Disney

Eartha Kitt. Carmen Miranda . Grace Kelly. Dynasty’s Alexis Carrington and Dominique Devereaux. Jennifer Lopez . Black-ish’s Jennifer Lewis. Enough said. Get a gorgeous one for $25 from The Wrap Life or $42 from Loza Tam.

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Gene Tierney. Photo by Silver Screen Collection/Getty Images.

The final touch: Caftan, turban, swimsuit, coverup, shadeswhatever. Your choice. Do a little reading up on the sundeck, then let your inner wildcat out.

You’ve done it! You are so glam. See you in St. Tropez!