Baggy Y2K and Accessories that Pop: The Fashion Journey of Jack Swales ’24

Swales’ aunt inspires him to wear and match different items.

Swales accessorizes with large jewelry pieces like rings and bracelets.

Jack Swales ’24 embodies a minimalistic Y2K style with a comfy white T-Shirt and dark jeans. He accents his outfit with a graphic Pink Panther baseball cap, an assortment of eclectic jewelry, and a pair of white Nikes.

“I think a lot of his staple [pieces] are the same but he seems more confident in the way he styles himself. I would say his style relies on classical colors and prints (such as primary colors, band tees, flannels) with fun accents like bandanas, sunglasses, pant chains, rings, jewelry, etc,” wrote Swales’ friend Nor Dehoog ’24 in an email to The Phillipian.

When planning his everyday outfits, Swales tries not to repeat clothing within a three-week time span, which gives him opportunities to express himself through different color palettes. He described his styling process and how he chooses his clothing to accommodate different days.

“I like to be a bit crafty with my outfit planning…[and] incorporate some piece of jewelry or some sort of accessory that is important to me, for example, rings, a necklace, a hat… I mix up these things and work around them… As I get further into the week, I start wearing nicer clothing. Fridays [especially], just to celebrate that the week is over and that I get to wear something nicer compared to Mondays,” said Swales.

Swales places emphasis on his accessories. One of his favorite pieces of jewelry is a matching penguin charm necklace he got with his friend, which they wear every day together. Swales discussed the importance of accessories in his style.

“When I wear accessories, I want them to be seen, like rings I can show-off, I always have the necklace hanging on the outside of my shirt rather than the inside, sunglasses every now and then… Those are things that I notice about other people, so I want mine to be noticed as well,” said Swales.

Since he was required to wear school uniforms prior to high school, coming to Andover gave Swales more self-confidence to experiment with more individualized fashion. Over the past few years, his sense of fashion has developed from button-ups in Freshman Year to baggy jeans and ’00s era fashion now.

“It has definitely been a journey… I remember in Freshman Year, I was wearing button-up shirts, khaki shorts, pants. Now, I can’t imagine wearing that every single day. Changing up my style gave me a lot of opportunities to be a little more confident in my body and feel better in the stuff I’m wearing… [I] developed from a kid who didn’t know what fashion was about to someone who cares about how they look every single day,” said Swales.

As he developed his passion for fashion, Swales started exploring more clothing stores like Urban Outfitters, Levi’s, and Hollister. He often discusses fashion with his aunt, who he attributed as his primary fashion inspiration.

“My aunt is not much older than me, so I love talking about fashion with her, vice versa. Whenever we feel excited about a piece of clothing, we would tell each other about it. [She created] a really good environment [for me to] show her my outfits. I just told her I got to do ‘Look of the Week’ and she was really proud of me because I [came] a really long way,” said Swales.

Additionally, Swales offered insight into what he feels the importance of fashion is. He talked about how people can explore an authentic creativity through clothing that they may not have the chance to express otherwise.

“People get the chance to feel comfortable with who they are in their sense of clothing, whether that be wearing sweatshirts every day, getting dressed up, wearing baggy jeans, ripped jeans, corduroys, or something along those lines. Fashion brings out the side of people that they may not know they have. As I go forward, I would definitely want to keep building this sense of style that I developed, while sticking to my roots too,” said Swales.