During the school year, comfortability is the route much of the student body chooses to follow when dressing for school. Popular pieces such as Madhappy sweatshirts, the rise of Parke crewnecks, along with sweatpants from brands such as Essentials, Nike, Brandy Melville and Comfrt have made their appearances on Poly Prep’s campus. However, with the new addition of mandatory Dress-Up Day on day seven, students have to get out of their cozy-threads and into their formal (or semi-formal) wear. This article acts as the ultimate dress-up day guide for male students at Poly, crafted through the opinions of three current Upper Schoolers. 

Spencer Udin ’27 said that three words he would use to describe his style are “attentive, coordinated and experimental.” He continued, “I usually like to wear tan pants, like khakies, and then I’ll do a button down, tucked in, and then a brown sweater with brown loafers to go with it.” Udin also experiments with color coordination and layering on the top half of his outfits. “The top half and the shoes are the things which make or break the outfit,” he said. In order to build the outfit, Udin enjoys shopping at thrift stores for sweaters, but equally finds that shops like “Zara, Urban Outfitters, Abercrombie and Fitch and other mainstream SoHo stores are good especially for a lot of sweaters.” He stated that many are also great for finding loafers, and recommends that others shop there as well. However, he strongly believes that “vests have started to become overworn on dressup days as a lot of them are styled the same with quarter zips. They are just preppy and in my opinion — overdone.” Udin feels vests lack a sense of uniqueness and how instead, he believes boys should start wearing pieces that reflect creativity. “I think boys should start wearing suit pants on dress-up days. Khakis are kind of the ‘safe option’ which is why I and other boys wear them, but I think suit pants, and especially baggy suit pants can be paired with a lot of different pieces.”

Jackson Arrington ’29 styles himself in pieces that both look formally acceptable, yet aren’t uncomfortable. “I usually wear a Ted Baker long sleeve collared shirt and Lululemon pants that I like because they are comfortable but also presentable.” Arrington also said that he enjoys shopping at Lacoste for more comfortable but dressed-up and good quality pieces. This way, he can look good and feel good on dress-up days. Though Arrington has worn this item himself, he believes that quarter zips are overly worn by Poly boys. “People should gravitate towards more fun and distinctive pieces,” he said. “Especially this year, everyone has been wearing them because they are trendy. It seems kind of pointless to me since they will go out of style.” 

For Isaac Wise ’28, the perfect dress-up day outfit looks like “a sweater paired with khakis or dress pants, and either fashion sneakers or loafers.” He enjoys dressing in trendy pieces, and described a particular green sweater, which he wears regularly. In pursuit of more pieces like this sweater, he shops for dress-up day outfits locally. “I shop where I honestly get most of my other clothes. So mostly Zara, Banana Republic, Urban Outfitters. You can also find much fancier clothes at places like Men’s Warehouse as well,” he said. Similar to Arrington, though he wears quarter zips, he believes they are overworn. “There is a lot of Ralph Lauren happening,” he said. “I think that we could go for different types of sweaters, different colors, and switch it up because everyone wears the same things.” Though he appreciates trends and embraces them himself, Wise believes there should be a sense of individuality in one’s style rather than just being a copy and paste of someone else’s. Wise said that individuality can be incorporated through “color coordination, unique patterns and leaning into the softer side of dressup day,” which he described as wearing just a sweater, rather than paring it with a collared shirt or parts of a suit. 

So, to summarize, Upper School boys should keep timeless staples to pull out for dress-up days. They should explore brands such as Lacoste, Abercrombie and Fitch, and Urban Outfitters, and use style as an opportunity to be unique. “It is all about finding clothing that suits you, while all the while remaining sophisticated and sharp,” Wise stated.