Where Are They Now? with Ruby Reeves
Where Are They Now? with Ruby Reeves
By Audrey Cooper — July 20, 2025
“I know I am headed toward something that feels genuinely true to me,” says fashionista and Square alum Ruby Reeves, as she looks toward her future in the unpredictable and exciting post-grad jungle.
Reeves currently resides in Charleston, South Carolina. She works full-time remotely as a client advocate for GIS Benefits, while also holding a part-time position at Hampden Clothing, a designer boutique on King Street.
Through working for Hampden Clothing and curating capsule collections for both customers and herself, Reeves has come to appreciate the value of investing in high-quality pieces.
“Spending a little more on timeless, well-made items rather than cheaply and fast-made clothing, can go a long way in building a closet that’s both lasting and versatile. Just a few staple pieces, like a nice blazer or good quality denim, can take you a long way,” Reeves said.
Reflecting on her past shopping habits, she added, “I used to buy cheap colorful pieces that were tough to mix and match. Looking back, they were not investment pieces and therefore only took up space in my closet and collected dust. I’m not saying pops of color are bad, but just be cautious on the longevity and practicality of the clothing you purchase.”
Prior to graduating from the University of Mississippi with a bachelor’s degree in business in 2023, Reeves was a member of Square’s creative team.
“Square filled the gap the university lacked in not having a fashion-oriented major. It allowed me to lean deeper into my love of fashion in a zero-judgment atmosphere.”
“My favorite Square photoshoot organized was called ‘Mother’s Love’. The shoot focused on the idea of passing down clothes to future generations in lieu of having grandmothers, mothers, and daughters who share pieces and the stories behind the clothing. Being someone who wears a lot of my grandma's and mom’s clothing, this shoot excited a sentimental emotion from me. When I wear their clothing, it feels like a bond tethering all of us together, especially my being so far away from home at the time of the shoot and even now. I think that shoot really played at those heart-strings and emphasized those emotions.”
After graduating, Reeves found herself becoming the go-to source for fashion advice among her friends and family.
“Nothing makes me happier than styling friends and family,” Reeves said.
Now based in Charleston, she described the city’s fashion scene as, “...not quite like New York, but I do love it. It’s kind of a boho-chic vibe here being so close to the ocean.”
Charleston also gives Reeves the freedom to experiment.
“I like to play around with a lot of different looks and test the limits a little bit, especially tapping into my creative side when putting outfits together for Hampden and seeing what kind of responses I get,” said Reeves.
Along with her work at GIS Benefits and Hampden Clothing, Reeves is also a founding creator for Shop Rodeo, a collective shopping community led by creators.
Reeves describes her personal style as “edgy with a twist” and “versatile and a little unexpected, but always evolving.”
“By edgy, I do not mean black and leather. I feel like it’s more about not conforming and embracing creativity; pushing boundaries and mixing in some unconventional pieces that might make others pause or hesitate, but that’s part of the fun of it,” Reeves said.
As far as fashion icons and influences go, Reeves said, “I have a few. Lately, I’ve been obsessed with Doechii…everything she wore at Paris Fashion Week was iconic. Her style is bold and unapologetic. Camille Charrière is another favorite; she’s effortlessly cool, often in slip dresses and short shorts. I feel like she embraced vintage before it was trendy, and I go to her page often for inspiration.”
“Another big [inspiration] for me is Iris Apfel. Her style was bold, bright, and full of fun accessories. I don’t think anyone did it better. She truly was the queen of accessorizing. She dressed with confidence every day, even as an older woman, and served as a reminder that age should never limit your style. She showed that fashion has no age limit. I also have to mention Carrie Bradshaw and “Sex and the City” for shaping a generation of fashion lovers, myself included. I'm currently on the hunt for a pair of vintage Manolos she wore in one episode.”
“If I could go back in time and give advice to younger me or anyone still in college, I would say to stop getting distracted by every shiny thing college throws at you… the parties, the drama, and that weird instinctive urge to care about what everyone thinks—it’s all a trap. I would remind myself to be myself, like really be my true self you know? Wear the outfit that you think is cool…even if others say it is a bit too much…and understand that it is okay to set some boundaries and say ‘no’ to the things that you do not want to do. Remember that the ‘coolest’ version of you is the one who is not trying to be anyone else,” said Reeves.
Reeves is not afraid to express herself, whether that’s through her fashion, personality, or ambitions.
“Style is about self-expression,” Reeves said. “It’s about wearing what makes you feel good. Be open to trying new things, you never know where your next look might be.”
Or in Reeves’s case, what the future holds for her.
To keep up with Ruby Reeves, follow her on Instagram.
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All images belong to Ruby Reeves.