Buying beautiful clothing didn’t always feel so dissonant and bad. It didn’t happen in the middle of the night because you couldn’t sleep. It didn’t happen because you were bored at work and typed “shirt” into the search bar. For thousands of years, people did not go on resale sites, buy things they didn’t need or even want, and then have to pay like $85 in tariffs. I’m pretty certain people didn’t buy $400 shoes while peeing in the Middle Ages, but maybe I’m wrong.
That doesn’t mean that buying clothing can’t feel good in the age of typing “shirt” and enduring the deluge of sponsored links, sponsored posts, and SEO-juiced lists that follow. In fact, I know shopping can feel better than that. Lately, this has been my quest: to only buy something if it feels serendipitous. What I have been craving is a way to buy clothing that feels fun and, crucially, offline.
Here’s an example: I’m with my friend Julian, and we’re having a perfect morning so we go to Outline, a store in Boerum Hill run by Margaret Austin and Hannah Rieke. It is a store with no e-commerce — no way to buy anything online. Instead, they have a mail-order catalog so perfect and beautiful that I have hung a page from it in my office.
Neither Julian nor I have plans to buy anything. Julian is sort of on the hunt for something to wear to our friend’s wedding; I’m sort of open to looking awesome all the time. So we decide: What if we…play dress-up? I caress a Molly Goddard cardigan and contemplate trying on this Grey’s coat. Julian has long coveted an Issey Miyake Pleats Please set. There’s one in the store; they don’t really know their size. Should they try it on, for research purposes? They do, and they look so good in it that they buy it on the spot.
This effect may be more intentional than either Julian or I could have guessed. “We want people to feel like they’re playing dress-up with us,” Austin and Rieke say when I reach out to them after my visit. They purposefully designed the store to evoke “the feeling of being in your friend’s closet.” Because the clothing at Outline is more expensive, as Austin and Rieke reasoned, everything should feel more considered. “It shouldn’t be as easy as pressing a button,” they add. “You should have to go in and try something on and think about it.”
Another recent memory, this time from a vintage store in the Catskills so good that I am reluctant to tell you the name: I was browsing with friends in between watching sets at a noise music festival. Did I need a lamé Lanvin blazer with an original runway tag? No. Did I buy it and, and do I now wear it all the time? Yes. It reminds me of fall in the Catskills, of driving in my friend’s car with all the windows down.
Contrary to what the experience of walking around the malls that are Soho and Williamsburg might lead you to believe, there are places in New York City where the shopping is good, where you experience the feeling of being in someone’s brain. A couple of weeks ago, I stopped by Surrender Dorothy, a store on West 17th that offers a combination of vintage and new clothing, all carefully curated. The store embodies the best of what IRL shopping should be: an escapist rabbit hole wherein you’re introduced to new clothes, new people, and an entire point of view. It’s run by three best friends: Ruby McCollister, Leah Hennessey, and Arabella Aldrich. The space is on the second floor of a creaky old building owned by the actor John Cullum and his late actor wife, Emily Frankel. The walls are painted slime green in homage to Emily, who McCollister said would have loved the color. There’s a bed in the middle covered in books written by friends and belts and bedazzled panties. The clothing there is playful, loud, luxurious.
While I’m there, Aldrich and McCollister show me some of their favorite pieces. Aldrich, who spent a decade in London and has a background in costume design, is adamant about stocking antique costumes. She shows me a whimsical men’s ballet ensemble from the 1940s, then a Jockey’s jacket from the 1930s. Pointing to the silklike fabric of one piece, she falls into a familiar refrain: “They don’t make clothing like this anymore.”
Most new items are sourced from UK designers whom Aldrich has scouted. She shows me a beautiful coffee-brown dress with a corset back designed by Sarah McCormack. It’s sexy, freaky, romantic.
To browse the racks at Surrender Dorothy is to take part in a conversation between oneself — a shopper — and the idea of style that its proprietors are putting forth. “A New York buyer is a very specific buyer,” McCollister says. “They want something sexy and practical.” Aldrich continues, “I think New Yorkers can have a limited idea of what sexy can mean in clothing. We’re trying to expand it.” To them, sexy is the same thing as playful. It’s the romantic Sarah McCormack corset dress. It is also an antique hand-painted mermaid costume, or a beautiful wool vest from central Asia. It involves having a little imagination, being open to a little bit of mischief — like wearing one of the shop’s S&M-y latex tops with a vintage lamé skirt.
It’s become de rigeur to refer to one’s customers as a “community,” but Surrender Dorothy actually functions as that kind of space, hosting readings and hand-sewing workshops. That week, the store is throwing a fundraiser for David Orkin, a leftist community organizer running for New York State Assembly. In other words: Surrender Dorothy is multi-faceted. It is a place where you feel good about hanging out, whether or not you’re spending money. As a result, shopping there feels fun.
The real revelation is that you’ll find plenty of stores like this once you know what to look for. There’s Women’s History Museum, a brand by Amanda McGowan and Mattie Barringer. They have a storefront in Chinatown where you can also buy vintage (and listen to extremely loud math rock). The aesthetic is sort of devil, sort of angel, like being in one of those Andrew Miksys photos of Lithuanian teens at a rave in the ’90s: Chantal Thomass body cons, antique girdles, French peasant bun covers, a lurex Kenzo top. Aldrich and McCollister also mention SC103, which just opened a storefront in Two Bridges. Maybe I’ll go there and finally get the big, weird bag I keep dreaming about.
What I’m getting at is that buying stuff on my phone while peeing makes me feel spiritually impoverished. It does not make me feel like I’m falling endlessly in love with clothing. It does not remind me of being 18 and contemplating a $30 velvet cloak in an antique store in Ohio and thinking: that’s so expensive! And then regretting not buying said velvet cloak for the rest of my life. All the clothing I actually care about — the clothing that makes me feel the most like myself — is clothing I bought in a store. All the clothing I truly am in love with is clothing I found while shopping with my friends.
Very rarely has this kind of purchase — or encounter, really — been coupled with the, “Oh no, what did I say when I was drunk?” feeling that I’ve gotten from spending too much money on something I bought online for no reason. Buying clothing should never feel like that. It should feel how I felt at the Ohio antique store as a teenager: scary, exciting, full of curiosity about how my life would change once I owned a beautiful garment, even if just for a moment.
