How I Shop: Brynn Whitfield

We all buy clothes, but no two people shop the same. It can be a social experience, and a deeply personal one; at times, it can be impulsive and entertaining, at others, purpose-driven, a chore. Where do you shop? When do you shop? How do you decide what you need, how much to spend and what's "you"? These are some of the questions we're putting to prominent figures in our column "How I Shop."

"Jessel's a fashion publicist, a couple of the girls had stylists, Jenna Lyons... I was like, 'I'm going to be the trash monkey of the group,'" Brynn Whitfield tells me. Fashion-wise, she's more then held her own among the new class of "Real Housewives of New York City" — no small feat when you're on screen with the woman who shaped how Americans dressed for many years. "It's so nice that everybody's like, 'We like what you were wearing.'"

Whitfield knows she was a surprising choice for this revamp of an iconic Bravo franchise. But even as she explains it, you can tell why she was made for television.

"I was actually in the south of France and I got a message — I thought it was spam or a crypto thing," she recalls. "Why would anyone want me? I'm not some rich, fancy Mrs. Bloomberg, whatever. I'm not married. I rent."

Plus, Whitfield is a comms professional: She knows how to tell a story, even beyond the quotes that become memes or the persona she's built on television. Her fashion, both on this season of "Housewives" and in real life, is compelling because there are layers to it, narratives that she's spun around why she wears what she wears. Her Alessandra Rich look for the reunion, which she described as "Salem Witch Trials meets Only Fans," is just the tip of the iceberg.

Ahead, Whitfield breaks down some of her stand-out looks from the season, how she went about shopping to become a Housewife, what it feels to get a compliment from Jenna Fucking Lyons and much more.

"We knew we would be announced at BravoCon, so that was the first like, 'Oh, shit. I need to think about clothes. It's going to be when people see me before they hear me.'

"I kept trying on things and thinking: Classic. Then, I just had this enlightenment: Carolina Herrera — no one will ever rip on you. It was between Carolina and Oscar de la Renta. I was like, 'That's it. I'm going to put this shit on my credit card, I'm going to Madison where the fancy ladies go and I'm going to buy something classy.'

"When I got there, I was like, 'Wait, this is not me?' But then I found the black pants with the attached skirt, and that's very me, because I love 1950s, '60s, 'Mad Men,' Lucille Ball, all that. Then, the top felt a little bit more sexy, with the see-through boning corset. So I was like, 'This is very me — serious on the bottom, party titties up top.' I knew I'd feel confident. I liked that there was some drama, but that, technically, I was wearing pants. It's New York. It's sleek. It's sophisticated, but a little sexy. That's the only time that I dressed in something that I love, but that I knew was a little safer, that people would be like, 'She looks nice and I'll give her a shot,' but couldn't form an opinion about me.

"We actually did have a stylist for the premiere that the network got us... I was in Europe, so I knew I couldn't really try anything on, so my friend who's a stylist was like, 'I'll do a pull for free, what do you want?'

"I operate by: What if this never happens again? What if this all blows up in our faces, it bombs, everybody hates it and never again will I get to have a premiere at 30 Rock? I guess maybe it's a scarcity thing I should work on. But I was like, 'Fuck it.'

"I knew that I wanted to wear sequins and that I wanted it to be form-fitting. I actually had sent her that LaQuan Smith dress. I thought it was red, and I wanted to wear red because New York City. When I got back home, it was pink, and I was like, 'Ugh, whatever.' It was in the midst of the 'Barbie' stuff, so I guess that's okay. But again, I was just, 'Titties out.' We've got to get ratings somehow. At the end of the day, sex sells.

"For the reunion, I had a whole vision. I wanted it to be 'sexy grandpa'. It's the evolution of 'date your dad' — now, we're going to grandpa. I have a lot of vintage Chanel necklaces, so I was like, 'I'll wear those. Can you find me a vintage Chanel sweater?' Then, I really liked that no-pants look that was really popular, so I was like, 'What if I just didn't wear pants?' I thought that'd be funny, if I went to my first reunion and just didn't wear pants. The stylist loved it, but we sent the photos from the fitting to the higher-ups and they were like, 'Maybe you should change.'

"Because I got that 'no,' I was like, 'I'm going to do 'sexy pilgrim.'' I had this whole metaphor... And I love Alessandra Rich. I had worn the brand in my confessionals, with this little pill box hat from the oldest hat company in London that I love, full Jackie O.

"Our premiere party and our reunion are the only times in our group chat where we're like, 'Girls, we're fucking good at fashion.' I'm glad we didn't look chaotic. Oddly enough, every time we'd show up to shoot, we'd be, unplanned, in the same color scheme, like beige or neutrals. It kept happening. It was actually hilarious. I remember Ubah and I had a girls' night out which never aired, but it was the two of us just being totally dumb and silly — we didn't talk about anything, it was just like, 'Brynn gets drunk and Ubah helps her hit on men' — and we both showed up and we matched. All season long, we all would do that. Maybe we've lost our edge after filming, but now we're not all synched. We're all fighting, and it's a mess now. But before, the periods and the fashion were synched.

"I just winged it [all season long]. I'm lucky that I have a lot of stuff. A lot of what you see is mine. For the trip to Anguilla, I didn't have to go shopping; I had just come from St. Barts, so I rewore everything. For Erin's anniversary party, I remember, it was like three hours before, I ran down to Intermix got the dress. I had the stockings from Jenna, and the faux fur white coat I'd had for two years. It was pretty chaotic. If we had a big thing, I would maybe buy something in advance, but for the most part, it was mine.

"It's how I dress: I don't really think about it, then, at the last minute, I'll [shop]. I'm a Revolve girlie, too, so if I have a couple days, I'll do a panic order, try the stuff on, return the stuff that I don't like. I'm fortunate where I live, where I can dart to Fifth Avenue and there's Zara, H&M, Maje... Proximity is important. It's like when you have a CVS on the corner, you always find a reason to go there.

"When Jessel and I went shopping, everyone was like, 'I love your look.' I totally forgot I even had a scene. I'm wearing a baseball cap, a $13 Hanes sweatshirt — which, by the way, is my favorite sweatshirt, I don't know why I just don't buy another one,  they're so soft — black jeans and thigh-high boots. Here's the thing: There's no difference between what I wore for the show and what I wear in real life. It's not like I have show outfits. A couple of the girls had a stylist or people that would come to their house each week with a rack of clothes and would do pulls from designers. I was like, 'Wait, what are we doing? What are we shooting? Okay, cool.'

"I didn't really even wear makeup that much, either... I just think it should be real. When I watch 'Housewives,' I like it when they're going to events and you see people dressed up, but every day, if I'm just meeting my friend to go shopping, I would wear the thigh-high boots and the dirty sweatshirt, and would throw on my coat on and run out the door. It's hard enough filming; you have to get mic'd up and do all this stuff — I can't add another layer of a full look.

"I'm going uptown to take my ex's family to the Met — don't get me started — and it's raining, so I'll wear my Paddington Bear outfit: green Hunter boots, black jeans, a turtleneck, my Uniqlo blazer and a raincoat. I steal umbrellas from hotels, specifically the Ritz Paris and the Ritz London, so I'll take one of those in my Paddington Bear look and head uptown. When it's fake raining, I have a vintage Yves Saint Laurent umbrella that I like to use as a prop. I also have vintage parasols for the summer.

"I love clothing. It's a hobby to me. I love vintage stores. I go to A Current Affair in Brooklyn and to the Manhattan Vintage Show. With vintage, the beauty for me is in the chase. I like the hunt. Pieces aren't coming to my mind, but stories of 'I found it this way' or 'I got it this way in Paris,' and how I feel when I wear it... For example, at Current Affair, I got this [sheer robe] from the 1950s. There's no tag in it. I don't know where I'm going to wear it, but I saw it and I know the woman who wore it was fucking awesome.

"I don't buy for, 'Oh, I have a wedding to go to' — I shop when I'm bored on the weekends and want to do something for myself: I get a coffee, I get a pedicure, I go shopping. I go through the sales racks, from Anthropologie to Saks, and I buy stuff that doesn't make sense but that I think is pretty. I actually have more reasons for why I shouldn't buy it. I'll never have anywhere to wear it to; it hangs up for two years and then eventually I'm like, 'It's time for you.'

"I didn't know until the very last minute what I was going to wear to the Michael Kors God's Love We Deliver event, but as I put on the blue outfit, I was like, 'Alexa, play 'Blue Moon' by Elvis. I'm listening to that in my apartment as I'm ordering my Uber, and I'm like, 'I'm going to tell people when I get there that I'm blue because the show's wrapping up.' It comes to me when I dress up, like my Paddington Bear look. I get excited.

"I just did a partnership with CB2, and my freshman-year roommate, Dharma, was telling them all these stories about how much I love clothes and design. She's like, 'Brynn didn't go to class the first semester. She brought her ironing board, and she'd be naked, ironing, like, 'Hey, roomie, how was class?' All she did each day was care about her look.' Mind you, I was shopping at the little local boutiques using my student loan money. But that's what brought me joy. I didn't care what classes I was going to. I was like, 'Oh, do I look cute to go to class?'

"I grew up not having anything remotely fancy, but I would be watching 'Sex in the City' and thinking about Manolo Blahnik and all those brands. When I was 24 years old, I didn't own a car, lived in between two 99 cent stores in Los Angeles and worked at Edelman — my first job out of school. I would go to Nordstrom at The Grove; there's the designer shoe section, and I try on these green feathered Giuseppe Zanotti heels that are bold and beautiful. I start crying. My rent was due, and these were one full check and half of my next check. This was very irresponsible me, but I said, 'Fuck it. I'm going to do it.' And I did. I still have the fucking shoes. I think I borrowed money from my brother to pay off my rent and ate Lean Cuisines and snacks stolen from the office on repeat. It's so me, because it's a pretty dumb thing to do, but I believed in myself. I knew that I'd be okay, that I deserved it, that I'd figure it out. That's kind of what my whole life has been. Did I do that again or make that a habit? No, but I was proud of the shoes. And in three or four years, I was able to go ahead and buy a pair of shoes like that.

"A few months ago, I went through a shitty mood and I showed up to my friend's house wearing this David Koma white feather thing and leather pants. I felt like a flamingo. I wish everyone could feel that way when you put on [something], because I'm telling you, it's different. I'm a different person. When I like my outfit, I feel so cute and confident, and I become the best version of myself.

"I've seen people that have so much money, and they go in and buy a whole collection. They have way nicer, fancier, more expensive clothes than me, but there's no soul, no connection. I'm not saying you can't wear a label head-to-toe — I love, for example, on the other 'Housewives' franchise, how Dorit will wear a label head-to-toe, and you can tell she loves it.

"I do have a lot of good basics that I can always default to. I have a Uniqlo blazer that I've worn nonstop for a few years. I just got an Anine Bing blazer. I'm comfortable with my own little look. I'm not a trend girl — I have more skinny jeans than I have cool whatever jeans. I love Stuart Weitzman thigh-high boots, I probably have nine pairs. If I feel gross, I can just put on jeans, those boots, a coat and a hat, and I feel fucking fabulous. I remember in college, I had this pink Purdue T-shirt that I thought was so cute, these shorts that you rolled over so you could see the white and these platform flip-flops, and I felt so cute in that outfit. You just have to have the things, a couple go-to's that, regardless of where I'm at mentally or how I feel physically, I can put them on and I'm me.

"I was talking to Jenna the other day, and she was telling me that she really loves my style. She's my friend, but sometimes when she says stuff like that, I black out and only hear Jenna Lyons giving me a compliment. It's nice having her and being able to get her opinion in one second. Like, the yellow-and-black dress [by Richard Quinn from the New York City Ballet Fall Gala], everyone I sent pictures of it to was like 'No, it's older.' But Jenna was like, 'Do it. I love it.' I worry sometimes that maybe I go too costume-y. I don't know how she explained it, but she was like, 'You don't cross that line. You're having fun.'

"This year, I wanted to do something that was colorful and joyful, and I had heard through the grapevine that it was going to be much different than last year, that it was going to be in celebration of the anniversary and of New York. So I wanted to do something that was structural and architectural. I kept thinking of buildings. I wanted something colorful and a little bit more dramatic. I wanted something that was as vibrant as the New York City Ballet. This sounds so cliché, but I wanted to give back with the dress, knowing I'd be on the carpet, what they'd given me for so many years.

"My grandmother taught me that money can't buy taste or cleanliness. I know sometimes you want to see those things or you want to have certain things that cost money — I just hope people understand you don't have to have money to have personal style. I know that's easier said than done, but I've been on both sides: You just have to be proud of what you wear. I wish that everyone could feel that way when we put on clothes. I know I'm blessed in very many ways and it's easy for me to just say these blanket statements, but I wish people could find that confidence in whatever they're wearing... You wear clothes every day, and they can bring you so much joy and can change your day. Even if it's something little, like a bracelet, just wear something that makes you happy."

Please note: Occasionally, we use affiliate links on our site. In no way does this affect our editorial decision-making.

Never miss the latest fashion industry news. Sign up for the Fashionista daily newsletter.