How I Shop: Gabby Windey

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.”

As the holiday season approaches, the urge to participate in joyful festivities and surround yourself with positivity is at a high. For some, the season’s spirit may be represented by freshly baked cookies or relaxing by the fireplace. For the apparel brand Cupshe, holiday cheer is represented by Gabby Windey.

From being a contestant on “The Bachelor” to becoming the “Bachelorette,” Windey won the hearts of America with her bubbly personality, wit and sense of humor. She then went on to compete on “Dancing with the Stars,” earning second place and growing her fanbase well beyond Bachelor Nation.

While the world got to know Windey’s personality through her funny quips and magnetic charm, her style was never fully uncovered. Each show had its own very specific wardrobe, so audiences rarely had the opportunity to see or hear about Windey’s sartorial preferences, nor did she get to explore them herself.

“On ‘The Bachelorette,’ they bring out huge racks of clothes already picked out in the beginning, so you go through and try on what you like,” Windey says.

Though Windey’s “Bachelorette” outfits were typically pre-selected or put together by an on-set stylist, that didn’t always mean she was forgoing her own taste — in fact, the star shares that, at times, having access to such a wide range of clothing helped craft how she defines her present-day style.

“I feel like you really get to fine-tune your taste a little bit and understand what you like to wear, what you constantly gravitate towards and what you feel good in,” says Windey. “‘Dancing with the Stars” on the other hand, the clothes were perfectly tailored to you (because they were custom costumes). That taught me how important tailoring can be, though I understand that’s not always accessible. I’ve only tailored a few important pieces that I wear a lot.”

Now, we get to see more of Windey’s style through her holiday collaboration with Cupshe. The 47-piece collection, with sizes ranging from XS to XL and prices between $15.99 and $42.99, was largely inspired by Windey’s memories from childhood of dressing up for the season. 

“Growing up in the ’90s, there was a lot of velvet worn during the holidays,” she says. “I have pictures of myself with a terrible haircut in a crushed velvet dress, so in the collection there’s velvet, there’s faux fur — it’s very nostalgic, the holidays in general.”

Ahead, Windey shares more about her style evolution, her collection with Cupshe, the importance of a good return policy and more.

“I mostly shop online, and I especially shop from stores that have a great, easy return policy. I feel like that really does make such a difference, if I shop from a store that has a two-week return policy or whatever, because then I know I’m never going to get around to returning. It’s nice to have insurance on the other side of things.

“I’m getting better at trying things on in person. I don’t actually like to physically shop because I feel like it makes me hungry — I get so exhausted. I hate shopping with other people. I’m a fast shopper, and I know what I like right away. I was just in Toronto with Robby (Hoffman), my girlfriend, and we went to this really great vintage store, and I tried on everything. It was all vintage, so I was like, ‘Okay, I need to be an adult and put in the effort. This is going to take time.’ So, I’m getting older and wiser.

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“The biggest splurge I’ve made on a fashion purchase would have to be my little Fendi baguette bag. It’s perfectly Paris-chic. It’s not so serious. It’s the classic Fendi pattern. It’s small, so it’s pretty useless, but it’s what I could afford. Luckily, it’s cloth, so I can shove as much as you want in it.

“I love having an excuse to get dressed up. I feel like it’s the performer in me. I loved that about ‘Dancing with the Stars,’ with all the makeup and the glitz and the glam every week. I was also a cheerleader for five years, so I love big hair and sequins. I also love being cozy at home. With my age and wisdom came looking for clothes that are more comfortable. I feel like there’s something for everybody in this Cupshe collection — there’s equal parts glitz and glam, cozy and comfy.

“You can’t take yourself too seriously. I feel like if you have a social media presence and are on television, people are obviously going to judge you, but it’s not really personal. I think heckling is a form of love. I love it when my followers and fans DM me and roast me. It’s my favorite thing to do. People come for my rugs all the time and I’m like, ‘You guys, I can’t get it together.’ But it’s like, who cares? I’m not an interior designer. I’d rather laugh at myself at the end of the day, and ultimately, I want to take risks.

“I love ’90s fashion. Jennifer Anniston and Kate Moss — they’re nineties fashion icons for me. I also love Zendaya; she always shows up so chic and elegant, but also sexy. I love how she embraces her womanhood.

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“I grew up on Air Force bases seeing my dad in that camo suit. They’re called ‘BDUs’ (Battle Dress Uniforms), and now I see them everywhere in vintage stores. I tell him, ‘Oh my god, Dad, do you know you’re a fashion icon?’ It’s actually so sick of him, but he has no fashion sense. He was forced to do that. But I can’t wait to get a pair. It reminds me of him. 

“I would say my personal uniform is jeans and a white tee of any kind. For during the day, it’s thoughtless — I know I like it and that I look put-together, but also casual. I’m really into the mixed metals moment right now, so I’m really trying to adopt it. I feel like with my skin tone, I veer more toward gold jewelry, but I like to play with silvers and all the other colors. I don’t want to put myself into a box.

“There’s this brand called Fancì Club that I love right now. I think it kind of had a moment last fall, but I’m slow with literally all trends. I just wore its dress to the iHeart Radio Music Festival. I also love Aritzia for basics. MISBHV is kind of a fun brand, and honestly Zara and Mango. I like to mix statement pieces with good affordable basics. I also shop on Revolve a lot because they have a great return policy.

“My favorite thing I’ve ever bought would have to be this vintage white sweater that’s knitted and zips up. I got in at a consignment store in Toronto, and it has a little frill on the back that looks like a bustle. It’s really feminine and chic.

“I always want to be unafraid to wear something that I think would be fun, but I’ve also missed quite a few times. That’s how you grow. I did wear this terrible outfit to dinner the other night — I didn’t even post it because I knew it was bad, but I was running out of time so I couldn’t change. I was so disheveled from pushing the fall agenda so hard. I don’t know what I was doing, but now, I know to never go back there.”

This interview has been edited and condensed for clarity.

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