Is it me? or my shoulds?

An examination of a sheer blue dress

Over the course of publishing this newsletter, I’ve realized I write about clothes to examine the stories I’ve told about myself, to myself, and others. Some of the stories I believe, others are narratives I’ve been told, whether explicitly or implicitly, and adopted as my own. Now, when I find myself wanting to wear something, but hesitating, I ask, “why?”

Last week I styled outfits with pieces I haven’t worn yet, but wanted to before the summer’s over. They’re clothes that I dreamed about in the depths of winter, comforting my pale, cold self with visions of frolicking around in the hot summer sun. Clothes that make me happy.

I laid the black slip dress, black one-piece, black sheer skirt, printed red jacket that I made into a dress, cream-colored slip, sheer blue dress, and black leather mini skirt on my bed. My hands danced across the garments. I immediately relaxed from the physical, a welcome reprieve from analyzing each of my thoughts before typing them onto the laptop screen.

I picked up the slip dress. I’ve loved it since I tried it on in Lucia’s bathroom in April 2022, but haven’t worn it yet. What about with a white button-down? No. This dress just wanted to be. I let that direction guide me for the rest of the clothes.

I photographed 15 of the outfits, airdropped 9 of them to my laptop, and uploaded the photos to a private Pinterest board to look at them all together.

What was the common thread?

Vintage lace slip dress from Lucia Zolea, secondhand Stuart Weitzman sandals from TheRealReal, vintage Dior bag from The Vintage Riot.

Vintage Bill Blass bathing suit from Lucia Zolea paired with a skirt I bought ~10 years ago.

Vintage Emanuel Ungaro jacket from INA that I had altered into a dress (but have only worn once because it flaps open when I walk), my Granny’s slip, Emme Parsons sandals, rented Gucci x Balenciaga bag from Vivrelle.

Secondhand DA/DA blazer from Lucia Zolea. The red sandals and printed bag really did make the outfit.

Hand-me-down Charles Tyrwhitt shirt from my friend Akhurapa that perfectly matched the SABRINA OL dress from Tumbao, Only Hearts brief, vintage D&G bag.

Hand-me-down Charles Tyrwhitt shirt, vintage leather mini skirt from JAMES VELORIA that my tailor Doretha shortened

TRAVIS TADDEO dress. They make all the pieces by hand in their Soho shop.

Secondhand Theory dress from Cauz for Pawz that Doretha shortened, vintage Ferragamo bag from Goodwill

The outfits were simple. Me, the garment, maybe one other item of clothing, shoes and a bag. No jewelry, minimal layers. My skin was the accessory.

I liked all the outfits, both the styling and how I looked in them, but I doubted I’d wear the black lace dress, blue sheer dress, or leather mini skirt beyond my bedroom walls because I didn’t feel comfortable in them outside my home.

I told myself, “they’re too sexy, too revealing”—or were they really? Maybe I just wasn’t confident enough to wear them. Or maybe I didn’t feel safe wearing them.

I sent a voice message to my friend Maddy asking for her take on the sheer dress. Maddy wears a lot of sheer things. She wears them well, and she wears them all over Europe. I also wanted to know, “where do you get the confidence to wear what you do? It is because you feel good in your body, the people you’re around, the spaces you’re in?”

She replied, laughing, “what I heard was, ‘How do I be more confidently slutty?’”

lol. Okay, that’s not actually what I meant.

I wrote back, “it’s more about what makes you feel safe/secure to wear whatever you want.”

“Well first of all, I was in Ibiza, so come on, everyone can be slutty in Ibiza, that’s the place to be it.” She’d just worn some epic sheer things there. This confirmed my hunch that the location was part of feeling safe and secure, but then she countered with a, “would I do it here [in London]? Yep, I would.”

I considered why my mind went to safety. I understood where the thought came from, but did I believe the underlying message, “she was asking for it?”

No.

I would reject this narrative, continue to do the work of unraveling this story from my subconsciousness.

Maddy continued, “I think a big contributing factor is the assumption…that you’re seeking attention when you’re wearing an outfit and sometimes you’re like, ‘I just love this outfit, I look great, I love wearing it’.”

Yes. Exactly. It annoys me that I sometimes worry about people’s perception of me because of what I’m wearing.

I’ve tried to nullify these thoughts with “effortlessly sexy” outfits—or what is more aptly described as “appropriately sexy” armor. I genuinely feel more confident in a slightly wrinkled men’s button-downs with jeans than a tight fitting dress or mini skirt because I can move the way I want to without feeling restricted, but it’s also a middle ground of sorts, me cultivating my tastes to what’s acceptable.

The next day someone asked me, “what’s you’ve favorite season for dressing?”

I blurted out, “summer, because you don’t have to wear a lot of clothes.”

I paused, laughing at my answer.

I’d never really considered this until I was in Costa Rica for six weeks and wore a bikini top, athletic shorts, and Chacos every day. I trekked through the jungle and around town, chest out, stomach displayed, knees rubbed raw from popping up on a surfboard, feet blistered by my sandals. My body was exposed, but I wasn’t doing it to be sexy, or to be anything, for that matter. I just liked the sun on my skin, the ability to move freely. I felt so damn good.

goop beauty editor Megan O’Neil recently shared a similar sentiment in her feature for

Leandra Medine Cohen

’s “What Do Moms Really Wear” series:

“I love dressing for summer — I love how the sun feels on my skin. I come outside and it feels like a massage, or a hug. The more of my body exposed, the better. There’s also just something about dressing and showing skin that feels celebratory in a way that’s just not trye in the winter. It’s not about feeling sexy, I just feel most like me. Which I guess is sexy, actually. It’s an authentic expression.”

I knew I felt comfortable wearing minimal clothes, but why there, and not here? New York is supposedly a place you can wear whatever, and people rarely bat an eye.

I think because the functionality of my Costa Rica outfit made me feel protected from people’s potential judgement about my lack of clothing. This New York summer heat gives me permission to wear less, but by choosing to wear something that’s colorful, something that’s see through—instead of clothing that blends in—I’m potentially messaging, “look at me!”

I don’t always want that, but I’d rather learn to work through my discomfort of what people might think, than edit my choices for their hypothetical opinion.

I vow to wear the blue sheer dress ASAP.

As for the slip dress and mini skirt, I realized what was holding me back from wearing them was simply that they’re restrictive. I just couldn’t move the way I wanted. Both outfits looked good in 2D, but what you couldn’t see, or wouldn’t know from looking at the photos, was that I popped out of the dress when I moved and the skirt hiked up my legs when I walked. I wish that wasn’t the case, because they’re truly beautiful pieces that make me feel giddy when I try them on, but they don’t fit me properly, or work for the life I live. I’ll keep them, for now—sometimes it’s fun to play dress up, without any intention of going anywhere.

If you find stuck on something, ask yourself, “why?” From a practical level, it’ll help you shop more discerningly; if you know the reason you aren’t wearing something, you’re less likely to buy it again.

Asking “why” also helps chip away at preconceived beliefs. For many of us, clothes are more than just a thing that covers our body. They’re a way we express ourselves, a hint into how we view our personhood, the messages we’ve received from others.

It’s worth exploring, and deciding for yourself what’s real, and what’s not.