103: RUBY REDSTONE
lives in dresses and Repetto Mary Janes.
For this week’s letter, I spoke with the singular Ruby Redstone. I met Ruby a few weeks ago at Mess, the hot pink and leopard print packed store she owns with her husband in the West Village. I bought a limited-edition doll named Miss Mess for my best friend’s baby, but was tempted by plenty of other items too—Leorosa knits, leopard-lined baby tees (a Mess exclusive with By Signe), and a pair of yellow short shorts whose designer I can’t remember. (Mess, charmingly, does not have an online store, encouraging an in-person experience.)
Ruby, an NYC native, is a writer and fashion historian. She’s known for her distinct personal style, which is, by my own estimation, part Marie Antoinette, part punk, and part retro coquette. I get the sense that Ruby’s style is so innate it can’t help but seep into everything she touches—from her store to her home to the way she writes and speaks. Ruby is a pure delight, and she has a lot to say about shopping and fashion. I’ll leave her to it. Here’s what Ruby has been living in lately.
Describe your personal style. What are you living in right now and why?
I feel like I always struggle to answer this question, which is funny because I overthink clothing professionally! My style is very much grounded in my love of history, especially my penchant for 1930s and 1960s silhouettes. I love color. I love strong contrasts: vintage dresses with contemporary silver shoes, streetwear with super-feminine skirts, and surf shorts with sequins. I’m very dressy, but I like everything I wear to have a little bit of a sense of humor.
In the past year I turned 30 and opened my own business, and it was also the first year in a long time that I wasn’t pregnant or immediately postpartum, so I finally felt like I settled on a formula of what I like to wear every single day. (I’ve never had a problem dreaming up outfits for big occasions). My everyday look is a dress and Mary Janes. Of course, I play around a lot within this formula–sometimes it’s a long silk slip and velvet flats, sometimes it’s a babydoll frock and red patent leather heels, sometimes I bring in bright red socks or tiger-print tights–but I know that it reliably feels polished and like myself.
How often do you shop?
Literally all the time. I’m the buyer for my store, Mess, so I am shopping for work all day long! And then I’m also shopping for leisure in the mornings and evenings and basically any spare moment, hunting for Prada on eBay and digging through racks of ratty old t-shirts.
I come from a long line of pretty epic shoppers. When my sister and I were little and our grandmother would come to town, we would skip school to go to Barney’s or Saks with her for the day, and it was the biggest treat. We wouldn’t buy anything, we’d just walk around admiring clothes, then sit down in the cafe for lunch and talk about what we liked over Caesar salads. My mom is an incredible shopper who has kept a mental tab of every sample sale happening and the gifts everyone is lusting after for decades.
I think a lot of people, especially women, feel a lot of guilt and shame about shopping, but I just love it. It makes me feel open and porous to the world, and nothing compares to the rush of feeling inspired and invigorated from a fabulous find. Of course, there’s a huge difference between shopping and spending money. I love walking through a department store and simply feeling the fabrics just as much as I love grabbing keychains and stickers at the Japanese deli by my house. I’m in it for beauty–not greed.
Where do you shop the most?
Not to be a shill but…Mess! I’m biased because it’s my own shop, but we really do have the best stuff. The RealReal and Poshmark are close seconds.
RUBY’S MOST WORN
My Repetto Mary Janes with a 3cm heel. I have worn these shoes almost every day since I was in college, including on my wedding day! They are simply the perfect shoe: the right amount of toe cleavage, a comfortable and leg-lengthening heel height, and durable patent leather. I think it helps to have a signature shoe when you experiment with clothes a lot. I can wear anything, and as long as I have my Mary Janes on, I feel like myself.
Hair clips! I wear a clip in my hair every single day. Typically it’s this one from Simone Rocha, which I actually also wore on my wedding day. It’s imbued with special happy powers because of that.

Old Miu Miu and Prada pleated skirts. Bonus points if they are in a strange material like metallic leather or water-repellent nylon. Perfect with a cardigan and the aforementioned Mary Janes for meetings, and just as good with a t-shirt and Converse for my kids’ soccer practice at the weekend.
My 16-inch strand of pearls, which I wear with gowns and t-shirts alike. My first fashion mentor wore pearls every single day, and when she died a few years ago, I started doing the same. It makes me feel connected to her and, in turn, also connected to this long line of women who have built the fashion industry. There’s also something so special and intimate about the way pearls are warmed by your skin as you wear them all day.

Anything and everything Cecilie Bahnsen. I’m not typically one to buy into a designer’s whole world, but I cannot get enough of everything Cecilie makes. Her vision of clothes that make you feel like a princess but are also comfortable to run around in all day is sublimely aligned with my lifestyle. She also made my wedding dress, so I guess I’m revealing that I want to dress like it’s my wedding day every day…?

Best buy of the last year?
Recently it’s been these red Miu Miu sporty sunglasses. I don’t often buy new designer items, but I tried them on and fell for them hard. You know when the addition of one small accessory suddenly makes every other item in your wardrobe feel fresh and exciting?

What are you currently searching for?
How much time do you have? I’m after a perfect 1950s gingham fit-and-flare dress, a Prada S/S 2012 car clutch, a pair of trousers that I don’t hate, a pink vintage basket bag, a 1920s drop-waist dress that I can wear to run errands, a Prada S/S 2011 striped strapless gown, a Claire McCardell playsuit, a classic Chanel flap bag with graffiti on it, a keychain shaped like a realistic frozen yogurt…
What’s your go-to bodega/coffee/grocery-run outfit?
If it’s warm out, an If Only If nightgown, suede flats, and a little vintage Jane Birkin basket. If it’s cold, a sweatsuit from Madhappy, my pink Saks Potts fur coat, and Moon Boots. A fur coat and a sweatsuit is a divine outfit permutation.
Does your style change when you go to work?
I try to always wear designers that we sell at Mess if I’m working in the shop or heading to buying appointments, which is easy because we really only stock things that I have tried, tested, and loved myself. The only true difference is that I make much more of an effort to do my hair nicely and put on a bit of makeup when I’m headed to work.
What’s your go-to out for a night out?
I hate changing my clothes, so if you see me out on the town, I’m definitely in that dress and Mary Janes combo. If it’s a real party party, I’ll put on my beloved Paco Rabanne paillette top, because what’s better than being your own disco ball?
What clothing item or accessory do you always travel with?
Our Mess exclusive organic cotton tees from By Signe because they’re warm and lightweight and easily layerable and have a hint of leopard. I also like to take a selection of hair clips because I can do the same dress every day and as long as I switch my clip, I’m good.












SINGULAR!!!
Ruby is so specific in her style!! I love!