You Don’t Have to Be Super Chill to Look Super Chill

Earlier this summer, dressed in a pair of white linen pants and a green knit bralette layered under a white button down left unbuttoned, I had an epiphany that I looked like the most relaxed human being alive. If I remember correctly, that day was pretty stressful. I had to be at four different corners of Manhattan within a two-to-three hour time span and the reasons for the travel sucked: two were physician-related and two were pertaining to work, but not the fun kind of work — the soul-sucking administrative stuff that requires spreadsheets and the like. When I walked into the office, we immediately began sounding off about menocore. I likened the look to that of a retired masseuse’s while Harling insisted that I looked like a member of the Nancy Meyers movie pack.

Haley may have suggested that I looked like I’d been baptized and Amelia asked if I had taken up surfing. All of these approximations pointed toward one thing: I looked super chill, huh? But how could it be when my day had been, and would continue to be, so g-dang stressful? Which is when it dawned on me that you don’t have to be super chill to look super chill. Dress like a lady of leisure who has never taken the subway and does not even know what a MetroCard looks like, if you’d like. It doesn’t mean you have to be her. Ditto that for, say, a TriBeCa mom who’s never left the triangle, or like, a local from the South of France. Before I give away all my approximations, I should just turn your attention to the below five looks, inspired by the lifestyles I would never want to lead, but sure as shit want to look like I do on the reg. We’ll start with that S of F local.

Dress Like: You’re from St. Tropez

I’ve never actually been to St. Tropez, but if I had to guess, they wear white linen 100% of the time and if they’re ever covering their feet, it’s only with straw shoes. I added a bandana scarf as a headband (to keep my hair back because, you know, it’s so salty in Southern France!), and a straw tote, which I really wish contained a baguette but is actually empty, between us.

Dress Like: That Lady of Leisure

Clearly this particular lady of leisure has been on the subway before, but I think that makes her more relatable, which I appreciate. Worth pointing out is that she seemingly refuses to use her hands, which is why she has opted for two handbags slung across her person as opposed to just the one, and I really appreciate her commitment to that lifestyle. In my guesstimation, her last name is something like van der ________ and she happens to be downtown only because they opened a Sant Ambroeus a couple blocks south of this subway stop.

Dress Like: You’re Three Different People (I’ll Explain)

Before I continue: I stopped washing my face this summer, basically because Harling told me to, and I worry that it is aging me — do you see what I mean? There are curious indentations that I can’t quite pinpoint all up on my face and for whatever reason, my hair feels like straw. But I digress. Top half of this outfit is an homage to Haley, who thinks the theme of my summer has been dressing like I am at my own baptism. Middle part of this outfit (shorts), riffs on the notion of a child getting dressed, only with these, I am more like a Jewish youth at his younger brother’s Bris and re: the shoes, remember that TriBeCa mom who never leaves the triangle? She bought these on Net-a-Porter.

Dress Like: Jennifer Aniston, Only Not

The only part of this outfit that maintains any semblance to the great J.A. is really the gargantuan light wash jeans, right? Right. But the great thing about playing the Dress Like game is that you get to make up the rules at every single juncture, so if I want to say that I’m dressed like Jennifer Aniston, but only in the event that in this conception, she had spent about two months interning at Man Repeller and thus picked up a couple of styling tricks along the way, then I’m going to do that. Cue the floral tank top layered under the striped button down and the orange-ass mules of me’dreams. Cheers.

Dress Like: An Unlicensed Masseuse 

Said masseuse may or may not be auditioning for the role of woman-who-owns-incredible-country-house in the next Nancy Meyers release. This one is probably my favorite because the pants are Eileen Fisher and dammit, they are comfortable. As for the rest of the outfit: I’ve deposited a white long sleeve t-shirt on my chest and layered over it a black bikini top only to cover said bikini top with a mandarin collar button down that features generous sleeves. The sunglasses are transition lenses so I never have to take them off (not that I would), and the bag is made entirely of pearls, which is totally the kind of thing an unlicensed masseuse who doesn’t have a table would wear. No? The slippers are by The Row, which I have recently started to call the brand for trust-fund masseuses. Very apropos if I may.

Now please excuse me, I’ve got to drink some Gatorade.

Photos by Edith Young.

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  • Natali

    St. Tropez and Jennifer Anniston ones are the coolest and super chill ones! 😀

  • Amy Wan

    This article speaks to my soul. I finally understand the aesthetic I’ve been trying to achieve for years. Thank you Leandra.

  • june2

    or whatever reason, my hair feels like straw – get a whole house water filter that removes chlorine AND chloromines. (The only ones that do are ascorbic acid filters…) Anyway, chlorine is wildly drying to hair/skin/brain.

  • “…the theme of my summer has been dressing like I am at my own baptism.”

    New hot trend: baptismcore

  • Harling Ross

    experiencing an acute need for that natasha zinko top

  • Aggie

    I kinda feel like #5 is dress like Phoebe Buffay except you need more ring action and I feel like that should be my new life inspiration for the winter-summer we’ve been having in London because showing your legs is over for us!

  • Coconut

    Your St. Tropez look is actually 100% Ibiza!! Love it

  • Kay Nguyen

    Your outfit of dress like you’re from St. Tropez is definitely on point! Will have to apply that <3

  • Emily

    I love all of this, esp. having been one of those ladies of leisure out in California for some years.. although I now am an owner of a metrocard I love dressing like I don’t have one (though funnily, back in CA people always diagnose me with having an ‘east coast vibe.’ re the hair, try switching shampoos! was having the same issue and that was my miracle fix.

  • Kate

    I just got a pair of mules that are gorgeous but giving me blisters on the top of my feet – is this common to this type of shoe? If so, any tips on how to avoid/deal?

  • This is amazing! Always so refreshing to read your blog posts! x

    Genevieve x

  • Carrieanne Luicadi

    Need the S of F look. Badly.

  • Basil

    I stumbled across a similar theme this summer (which in London lasted for about three glorious weeks. RIP British summer, you’ll be missed).
    My go to summer persona was Fran Fine (of The Nanny)’a mother Sylvia on holiday in the South of France. It featured smart cotton dresses, BIG gold jewellery, gold leather sandals and my hair as pouffed as it would go (i.e. Not that much. But I tried).
    I had an awesome summer

    • Amanda June Brawner

      Writing from London; RIP British summer, indeed (how depressing – I am not from here originally!). About to visit family in the southern US and will NOT be packing my “summer sweaters”! *Thrilled*

  • TinySoprano

    Those orange mules!! They’re like an Aperol spritz in shoe form!

  • allison fargo

    me dressing like an unlicensed masseuse is me trying to prove i am indeed a ~cool chill girl~ and not the extra ho i often act like

  • Sofia

    Lady of leisure is wearing Lisa Corti…