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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."

"Some models will talk about their first pair of Louboutins, but I'm more interested in my first pair of Uggs."

Teddy Quinlivan has walked runways across the globe for designers including Louis Vuitton, Haider Ackermann, Paco Rabanne, Michael Kors, Thom Browne, Christian Cowan, LaQuan Smith and Christian Siriano, among others, and appeared in countless campaigns and editorials. She's been a vocal advocate for the LGBTQIA+ community and for trans visibility, after sharing her story with CNN in 2017. Her latest project connects all this to another part of her life: She's a born-and-raised Bay Stater, who can tell you when and where she got her first pair of Ugg boots. (Middle school, at a small shop in Cambridge, Massachussetts.) 

Teddy Quinlivan is the latest subject of Ugg's "Feel You" feature series.

Teddy Quinlivan is the latest subject of Ugg's "Feel You" feature series.

"Ugg reached out to me, but I've been paying attention to Ugg recently, because a lot of my LGBTQ friends in the industry — whether it's Kim Petras or Susanne Bartsch or Linux — have all collaborated with [the brand]. So it was kind of in the atmosphere, around what I was doing anyways," she says. "Of course, anybody who grew up in the United States, especially if you're from the East Coast like me, is very, very, very aware of Ugg as a brand. I'm pretty sure everybody in Massachusetts has owned at least one pair of Uggs. It's a staple, to the point where it's almost become a meme about being from the Northeast is having a pair of Uggs during the winter." 

Aside from that personal connection to the brand, Quinlivan was excited about the reason for the outreach: a feature in Ugg's monthly "Feel You" series, timed to Trans Awareness Week, accompanied by a monetary donation to the organization of her choice — in this case, $10,000 to the Ali Forney Center in New York City.

"It's not very often that you work with a brand that wants to give back in some way," she says. "A lot of times, brands use LGBTQ people in a [tokenizing] sort of a way, like, 'Look, we do our part, we support the LGBTQ community, here you have some A-list LGBTQ people who are representing our brand.' But when I saw that [Ugg] wanted to help to give back to a cause that I felt was really important, it made the collaboration that much more special and that much more personal."

Quinlivan for Ugg.

Quinlivan for Ugg.

That first pair of Uggs, by the way — Classic Chestnut — was a gift from Quinlivan's mom and "a huge deal for me": "I finally felt like, 'Oh my God, I'm just like one of the cool girls,' because all of the cool girls in my school, they had a North Face, an Ed Hardy T-shirt — back in the day when Ed Hardy was really cool and popping — leggings and a pair of Uggs. It was the staple New England girl outfit, and I was just very happy that I could join the club."

Ahead, Quinlivan talks about aligning herself with brands and creatives that have something to say, reflects on how her style — and the way she shops — has changed as her career has progressed and and, of course, reminisces about that first pair of Ugg boots. 

Quinlivan, in her Ugg "Feel You" feature.

Quinlivan, in her Ugg "Feel You" feature.

"It was a huge deal for me, to get these [first] Uggs. I must've been like 11 or 12 years old — I was pretty young. I remember they were impossible to find because everybody was buying them. We had gone to so many stores looking for them, and they didn't have them anywhere. We finally found them in a small shop in Cambridge, Massachusetts that had them in my size. Me and my mom seized the opportunity, and that was it: That was my Christmas gift for the year, and I couldn't be more elated. I wore those Uggs to smithereens. I wore those Uggs until they were filthy, dirty, disgusting, completely unusable. I wore them like every single day. 

"Anytime a brand is open to the idea of working with somebody who's not a straight, cisgender, white person — or just any kind of character out of the box — I think is great. I'm very fortunate anytime any brand wants to work with me, because I'm so outspoken and because I'm trans and because of what I represent. That sounds the alarm to a lot of different, more corporate brands that want to have a very non-political message. When you work with somebody like me, automatically, there's a meaning to it. It means something just because of the stance I've chosen to take.

Quinlivan for Ugg.

Quinlivan for Ugg.

"Being able to work with a brand like Ugg is really special because it has such mainstream appeal, and I feel it's one of those brands that you wouldn't expect to take a stand. And it's one thing to take a stand, it's another to put your money where your mouth is... Some kind of financial backing to put towards a cause makes a huge difference. At the end of the day, the way that we're able to protect trans people or LGBTQ people, for that matter, is through investing in resources for those people. Anytime that a project like [this] comes up on my radar, it's important to me to feel like they're not only investing in me as a trans person and as an artist, but they're also making a point to give back in a way that's significant and is going to leave an impact. Money going to a cause that's important, oftentimes, is the way to do that.

"My whole life, I used fashion as a vehicle of self-expression, and it always brought me so much joy. When I first started modeling, I felt it was really important to make an impact with what I wore. I would take my paycheck from these fashion shows, which don't really pay a lot — people think we get tens of thousands of dollars to walk shows, that's totally not the case — and instead of staying in a nice hotel or investing in something wise, I would go to Miu Miu or Prada and buy whatever the craziest thing in the store was. Because I was living a dream come true. It was the first time I had been in front of an audience, and I had been following people like Hanne Gaby and Kasia Struss and all these models from the era before I became a model, when model street style, specifically, was a huge deal. I wanted to emulate that energy, but also take it a step further, so I was blowing all my paychecks on crazy, crazy outfits.

Quinlivan photographed on the street during New York Fashion Week in February 2016.

Quinlivan photographed on the street during New York Fashion Week in February 2016.

"The more time I've spent in the industry and also making those investments in clothing and in fashion, you start to realize that the staples are the things that you keep forever and that feel the most precious and meaningful. So my style has shifted quite a bit, from being like, 'Okay, I'm going to buy the most crazy pair of jeans,' to now wanting the most classic pair of jeans that I can have for the rest of my life. At the end of the day, luxury isn't just about looking a specific way — it's about feeling a specific way, it's about the clothes having integrity and lasting a long time.

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"I definitely have kept some of [those pieces] just because they're so special... and because I have so many amazing memories in them. Even if I never wear them again, collecting clothing has always been a part of the legacy I want to leave behind. There's going to come a time when I want to donate these clothes to a museum or a place where people can look and see how special they were.

"It's really precious and special that I have a lot of these clothes and that I've been photographed in them from a young age. It's been a major privilege to be photographed as much as I have. And I've always felt like the street was more of a runway than the actual runway — that's just my philosophy since before I was a model: The way that people see you in the street, the way that people photograph you in the street is almost more impactful than what you see on a runway, because what you see on a runway is so constructed and doesn't necessarily have as much of an organic feel as the way people style clothes on the street. I wanted to bring the runway to the street, and I felt like I did a pretty good job of that in my early career. I still enjoy doing that sort of thing now.

Quinlivan photographed on the street during Paris Fashion Week in September 2019.

Quinlivan photographed on the street during Paris Fashion Week in September 2019.

"Now I pull a lot my style inspiration from... I hate to use this reference because everybody uses it now, but Princess Diana out and about on the town, or pictures of Bridget Hall in the '90s or of different First Ladies, different senators — just looking at the way that women in power have dressed and done it so effortlessly, then adding a twist to it. I never want to be just the jeans-and-T-shirt kind of a girl because I'm not a princess and I'm not a First Lady. I do like to add a little bit of spice to it. For me, it's about wearing a classic outfit maybe with a really interesting shoe, or a simple black dress with a fabulous vintage fur coat.

"I'm a huge fan of the high school girl aesthetic. A plaid pleaded skirt, for me, is something that will never go out of style. It can go with anything — you can dress it up and have it be a full fit like 'Clueless,' or you can dress it down and look like a preppy New England school girl. That specific piece has always been a staple in my wardrobe. I also love a long coat. My aunt had this beautiful long cashmere coat; when she passed away, I didn't want to wear it because the memory of was too painful. Now that so many years have passed, I really feel like that's such a classic, amazing piece, and something I would wear, for example, with a plaid school girl skirt.

"For me, in order for clothing to have longevity, besides it just being really well-made, it has to have some kind of sentimental value to it. Because at the end of the day, that's the thing that's going to make you keep going back to those pieces, having an amazing memory in those clothes or them making you feel a certain way. The school girl skirt, I went to boarding school and didn't have a dress code, but I always fantasized about that particular style of dress and that aesthetic. Because I never went on to go to college, I'm kind of like stuck in this high school, boarding school aesthetic, but that's a piece of my history and a piece of my life that's really meaningful to me, just like that coat that represents my aunt and how she dressed and what a style icon she was to me. The pieces that are staples in my life and hopefully in everyone else's are the ones that have the most sentimental value.

"I feel very personally about representing certain brands and certain designers. There are some designers where I just don't believe in their work — they're appointed to very big houses and maybe a lot of other people identify with their work and can enjoy it for themselves, but I might've had a negative experience meeting them out at a function or I had a casting with them and thought that they were an asshole or whatever. There's a million different reasons why I wouldn't wear something. For me, buying a pair of $1000 shoes is me endorsing that designer, especially if I'm going to be walking around the streets of New York and being photographed by paparazzi. Wearing these clothes is an endorsement of those brands. I make it very clear that my style choices are me letting the world know that this is a brand that I feel really confident in, but also that I think makes work that's worth putting on my back... You know how Anna Wintour says, 'To be in Vogue has to mean something'? I feel like it has to mean something to be worn by me... When I wear a designer or when I walk a young designer's show or when I endorse a brand, it's because I truly believe in that person and it's because I truly believe, in a very Isabella Blow type of context, that this is somebody who's worth investing in, worth paying attention to, worth shouting out and worth giving that praise to.

"As a model, my body isn't just something to take photos of, necessarily — it also has to represent something. My brand as a model, what does that represent? And what does that represent to these young designers? I think that designers have always noticed that about me and have taken a shine to me in that way, actually. The designers that I do believe in understand that, and that's why it's meaningful for them to give me the clothes to wear and that's why it's meaningful for me to wear their designs.

"There are a few different younger brands that I'm obsessed with at the moment. Wiederhoeft is made by this boy named Jackson; he used to be one of the star designers at Thom Browne, so I met him when he was working [there] and now he's launched his own brand. His clothes are just so couture, so amazing. He's from New York, but you could place this boy in any major fashion capital and he would thrive because he has such a unique vision. Everybody should keep their eyes out for him. I love Ludovic de Saint Sernin — I think what he's doing is incredible, his open embracing of sexuality and fluidity in fashion is amazing. Andrea Skye Brocca just graduated from Central Saint Martins and Lady Gaga wears his clothes. He's considered to be the youngest couturier in [the world], and he's just a spectacular designer.

"To shout out some brands that aren't quite as high fashion but are doing such amazing things: I think Are You Am I is a great brand started by an incredible girl that has really taken the world by storm. It's affordable. It's really chic. It's really cool. Lana [Johnson], the designer of Orseund Iris, is amazing, and [has] captured that New York, downtown-Brooklyn girl perfectly. She's always putting out really interesting designs. Also, Poster Girl has been around for a while, but it's really taking off right now. It has a very unique design aesthetic — it's very Y2K, very of-the-moment. It's also moderately priced as well. 

"While it's amazing to see a lot of these younger designers dip their feet into high fashion, it's great to see a lot also making clothes that are luxurious but affordable. At the end of the day, not everybody can go into a store and buy a $3000 corset or a $3000 dollar dress, but they want to feel special, luxurious and like they're buying something that's meaningful and important. You shouldn't have to go to Zara or Shein or any of these fast-fashion places to buy clothes that are affordable and luxurious when you can go straight to these designers and invest in a $200 dress. I love that the market is shifting more to a more affordable, younger designer, high-end vibe.

"A classic staple piece that I'm really loving, that I've invested in... a Ralph Lauren cable-knit cashmere sweater. At the end of the day, I'm a little white Catholic girl from Shrewsbury, Massachusetts. It represents something to me. It's timeless. I've worn this sweater so many times, to the point where I'm taking the razor that I use to shave my legs to shave off the pilling from it. I just bought a second one. It's chic and it kind of goes with everything. It goes really well with my school-girl aesthetic. It's funny, when I was growing up, I was trying so hard to get away from that — I just didn't want to be that girl, a 'basic bitch.' But now as an adult, you start to realize, 'Actually, those basic bitches were onto something.'

"I have three friends that I will send things to, that all have amazing style. One of them is one of my trans girlfriends, Cameryn Ruby. She's also a model, and we have very, very similar style. She always is a great person to consult, and I almost always will agree with what she has to say. My friend, McLayne [Ycmat] — he's an art director, so he has a really good eye. Then my friend Ashley Soong, who's a fashion photographer. I'm lucky that I have all these amazing industry friends that have known me for so long that I can turn to. It's funny, when I'll be like, 'Oh, do you like this? Should I buy this?,' they'll describe it back to me like, 'That looks very Teddy.' They know me so well, they know what in the long term I'll get the most use out of.

"We're in a very, very scary time in the world right now. My generation, younger millennials and Gen Z feel very nihilistic about the state of the world and the future, and I think that's why we're embracing fashion so much more strongly than perhaps older millennial or boomers. We need to find pieces of joy where we can. We're going through a fashion renaissance all over the world, but especially here in New York and on the East Coast and in Los Angeles. There's just something happening. There's something in the air. 

"I feel very passionately and strongly about making sure that everybody supports these younger brands and smaller businesses that are trying to make a name for themselves in this business that's so dominated by fast fashion. It's very hard to make a stamp for yourself and to put your name out there when you're creating something, when it gets worn by a big star and then fast-fashion brands replicates it within the span of two weeks and sells it at half the price. It's so important to celebrate and also support young talent in our business. That's where the energy lies. It makes you feel good after you've made a purchase from somebody like that. It's up to us as a generation to prove that there's space for us and that we can accomplish anything, despite what these huge corporate entities would like us to think or would like to mislead people to think. The power is in our hands because at the end of the day, we have the pocketbook. Also, I don't know how many LGBTQ CEOs are at the helms of these huge corporations, but I can guarantee you, a lot of the owners and creators behind these small businesses are members of our community. If you want to support the community, a great way to do that is to put the money back into the pockets of the people who are trying to lead this fashion renaissance."

This interview has been edited and condensed for clarity.

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