Fashion trends continuously cycle, but few pieces hold as much weight as a sweatshirt. Hoodie season is approaching, especially as the temperatures in New Orleans slowly begin to cool down. As I am looking through my own collection, I couldn’t help but think about the continuous evolution of branded crewnecks and hoodies.

What is it that makes a simple hoodie so appealing, and why do certain logos, fonts, and even cities have such an influence on phases in our lives? I am curious about these aspects as I have fallen victim to the fast-paced trend cycle, owning at least one sweatshirt in each category that I am about to mention. From preschool class to college campus, here are the sweatshirts that have stood out the most to me.

Images via Pinterest, Cosmo, and Vogue by Leah Radnay.

Reflecting on photos from my early days, it seems like Gap was my first “big deal” sweatshirt. It was a classic zip-up with huge GAP lettering that felt like a uniform in my early school years. At this age, we were yet to choose our own style, but it was familiar that the sweatshirts were simple, safe, and instantly recognizable.

In recent years, Gap has leaned into its classic upbringing with new creative strategies and collaborations to rebrand itself. Still, I rarely hear people making an intentional trip to the store to buy the hoodie we all once wore and loved; instead, they make thrifted finds as a way of symbolizing their rediscovered childhood.

Victoria’s Secret PINK print ad Spring 2009

If Gap defined our childhood, then Pink shaped the tween and teenage years. Their bold lettering and bright colors were impossible to miss. Victoria’s Secret had always been tailored for an older audience, yet their spinoff brand, Pink, made tweens like me feel just a little older and cooler.

Although Pink hoodies have faded from the mainstream, they are central to Y2K fashion aesthetics. The Victoria’s Secret brand itself has never really disappeared; its curated presence on resale shops like Depop and its iconic fashion show legacy have kept it alive. Items from past Victoria's Secret collections often sell for far more than their original retail price, but we have yet to see a true comeback or desire for these hoodies.

Brandy Melville was never exclusively known for their sweatshirts, but for a variety of graphic tees and unique bottoms that carried a certain teenage status. However, one notable piece was city-stamped sweatshirts, which said more about where you had been, and not just what you were wearing.

Being from Chicago with no store nearby at the time, I would make Brandy Melville my own souvenir shop. Trips around the US called for grabbing a $30 oversized sweatshirt stamped with “Newport” or “SoHo,” and somehow everyone else seemed to be doing the same. Owning one of these hoodies subtly hinted at travel, trendiness, and being “in the know.”

Although their sweatshirt releases may have slowed down, the brand itself has not. Brandy Melville is well-known for its affordable, go-to basics, such as tank tops, sweatpants, and tees, which are rooted in a simpler and minimalist aesthetic.

Eventually, there was a complete shift in sweatshirts, going from casual basics to luxury statements. Two West Coast-born brands, Free City and Aviator Nation, had their first releases in 2001 and 2006, and likely inspired Madhappy’s founding in 2017. All three have increased popularity in matching lounge sets, as their logoed hoodies and sweatpants can be worn together as a complete and intentional look.

These brands continue to dominate the high-end hoodie scene by using high-quality fabrics, bold branding, and exclusive drops to justify their high price tags.

The fall 2025 Free City x Madhappy campaign feels like the right step in loungewear culture, and several pieces sold out almost immediately. Because of the consistency of both brands’ vibes (Free City with its artsy edge and Madhappy with its optimistic branding), they elevate each other's images. The collaboration not only reinforces their place in the luxury loungewear market but also reflects how sweatshirts have transformed into highly coveted and marketable lines.

In more recent times, hoodies have become personality-driven. On campus and in my own closet, I find the most popular items are sweatshirts that are simple in design but elevated in price. Many of the founders of these brands started as online personalities, including Paige Lorenze’s Dairy Boy, Chelsea Parke’s Parke, and Bridget Bahl’s The Bar.

These brands are thriving because their followers feel connected to the lifestyle behind the logo. Wearing a sweatshirt your favorite influencer designed isn’t just about comfort; it’s about signaling alignment with the founder’s aesthetic and values. The hoodie becomes a symbol of being part of a certain world, in a more unique way than it does when bought from a more well-known brand.

Valentine's Day Dairy Boy campaign with Cosmopolitan 2025

From our very first GAP zip-ups to turning on notifications for influencer-exclusive hoodie drops, sweatshirts have continuously reinvented themselves while staying rooted in comfort and identity. Each era carries its own story through nostalgia, status, travel, luxury, or lifestyle.

The real question is: what’s next? Will the next big hoodie be a nostalgic comeback, a high-fashion collab, or a new influencer-driven cult brand?

Whatever it is, one thing’s certain: hoodies will always find their way back into our closets.

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