The aesthetic that I focused on for my upcycle project was the “ski bum” aesthetic. This aesthetic reflects a mindset where skiing is the number one priority. This mindset is accompanied by bright colors, fun fabrics, second-hand clothing, and a care-free attitude. There are a few aesthetics that come to mind when I think of the opposite of these ideals. The two main ones are the “preppy” aesthetic and “business core” aesthetic. I will be focusing on the “preppy” aesthetic for this post and how I would make a hat to reflect it.

The preppy aesthetic has been around for over a century, originating in the late 1800s as a status symbol among young men attending elite Northeastern prep schools and Ivy League universities. This style was heavily influenced by traditional British tailoring and had a refined, collegiate look. Typically clothing included button-down shirts, loafers, knit sweaters, and blazers, all reflecting a sense of sophistication and exclusivity.

By the early 1900s, women began adopting preppy fashion as well, incorporating structured skirts, blouses, pearls, and tailored blazers. The style remained a signifier of wealth and social standing throughout the mid-20th century, with brands like Brooks Brothers, Ralph Lauren, and Lacoste gain popularity and putting this style into mainstream fashion. The 1980s saw a major resurgence of preppy style, particularly with the rise of “Ivy League” fashion, which embraced pastel colors, polos, chinos, and nautical influences. Even today, preppy fashion maintains its association with country clubs, sailing culture, and timeless, clean-cut clothing.

There are also various kinds of the “preppy” aesthetic that have gain rise in recent history. One example is the one explained above, and another is one that has gained popularity on TikTok. It contains very bright colors, flashy clothes, and puffy skirts. This style has more in common with the “ski bum” aesthetic, so it is not the one I am focusing on.

The ski bum and preppy aesthetics I am looking at are on opposite ends of the fashion spectrum. While ski bum style is casual, colorful, and functional, preppy fashion is refined, neutral-toned, and polished. Ski bum fashion embraces thrifted and worn-in pieces, often looking intentionally mismatched or layered for practicality. On the other hand, preppy style follows a structured and put-together look, often featuring coordinated color palettes, tailored fits, and traditional fabrics like wool, tweed, and cotton.

Another key difference is the attitude each aesthetic represents. Ski bum fashion conveys a laid-back, adventurous spirit, prioritizing experiences over appearances. In contrast, preppy fashion has historically been tied to status and social prestige, reflecting a more curated and intentional approach to dressing.

For my upcycle project, I will create a hat that embodies preppy fashion while maintaining a sustainable approach. Similar to my ski bum-inspired project, I will start by thrifting a baseball cap. To give it a preppy feel, I will sew a rope along the brim, a common detail found on vintage nautical caps often associated with Ivy League and country club aesthetics. Additionally, I will attach a patch, possibly featuring a crest or emblem, to reinforce the structured, traditional look of preppy fashion.

This project highlights the contrast between the two aesthetics while emphasizing the sustainability of upcycling. By transforming a second-hand item into a piece that reflects a polished and classic style, I can explore how fashion can be reinterpreted through small but impactful design choices. Ultimately, this hat will serve as a blend of sustainability and preppy tradition, proving that upcycling can work across different fashion aesthetics.

Links

Bowen, Sydney. β€œThe History of Preppy Style.” Her Campus, 28 Sept. 2023,
https://www.hercampus.com/school/ku/the-history-of-preppy-style/.

Farra, Emily. β€œThe Evolution of Preppy Style.” InStyle, 10 Oct. 2022,
https://www.instyle.com/preppy-style-evolution-5386615.

β€œPreppy Style.” The Gentleman’s Journal, 15 Mar. 2023,
https://www.thegentlemansjournal.com/article/preppy-style/.

Hubbard, Lauren. β€œHow Preppy Became Cool Again.” Harper’s Bazaar, 18 Nov. 2022,
https://www.harpersbazaar.com/fashion/trends/a42710995/articles-of-interest-fashion-podcast-preppy-style-history/.

Kiel James Patrick. β€œOld Salt Yacht Club Hat.” Kiel James Patrick,
https://kieljamespatrick.com/products/old-salt-yacht-club-hat.

4 Comments. Leave new

  • Matthew Cumpton
    February 11, 2025 9:37 pm

    Your post does a fantastic job comparing and contrasting the aesthetic between ski bum and preppy. What color hat are you considering in order to embody the preppy aesthetic?

  • Your post does a great job breaking down the ski bum vs. preppy aesthetic. I like how you explain not just the clothes but also the mindset behind each style. The contrast between the laid-back, thrift-heavy ski bum look and the polished, status-driven preppy style is really clear.

    I also think your upcycling idea is super creative. Thrifting a baseball cap and adding classic preppy details like the rope and crest is a smart way to blend sustainability with tradition. One thing I’m curious about is are you going for a more old-school, classic preppy look or something closer to the 1980s pastel style? Since preppy fashion has changed over time, it’d be cool to know what version you’re pulling from. Great job and really interesting!

    • I was thinking about pulling more from the old-school, classic preppy style because to me it is a but more interesting than the newer preppy fashion.

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