It’s always fun to look back on those who came before us and smirk at their interesting fashion choices. So why not take a trip down memory lane and revisit the infamous Y2K and ’90s prom looks? Here are six of our favorite styles and trends that are sure to bring back all those good old memories. And if you weren’t around back then, at least they’ll make you laugh.
1. Unconventional Footwear
Throughout the ’90s, many young guys traded in men’s dress shoes for a pair of boots or sneakers. Whether you were goth, grunge, preppy or anything else, there was an unconventional boot and or tennis shoe for you.
Wearing boots, dress sneakers or some style in between to prom is a way to express yourself and make a statement. Wearing casual shoes with formal clothing back in the day showed that you weren’t afraid to be different and stand out from the crowd. It was also symbolic of rebellion against traditional norms. Channel that energy into your ‘90s prom look this year!
2. Punk Rock Haircuts
The ’90s was full of punk and grunge-inspired haircuts. If you wanted to really stand out at your prom, a punk rock-inspired haircut was the way to go. These haircuts often included shaved sides, mohawks and spiky tips. The term “spiky tips” refers to when hair is gelled up, so it stands straight up in multiple directions. This look was especially popular with guys, but girls flocked to the trend, too.
The key to nailing a punk rock-inspired ‘90s prom look is all in the attitude. The way you style your hair and clothes should show that you’re unapologetic and confident in your own skin. The especially bold guys would slap on a bit of eyeliner long before it was mainstream.
3. Bold Hair Highlights and Frosted Tips
The pictures don’t lie. These hairstyles were everywhere. From famous boy bands to your next-door neighbor Linda — and forever etched in prom photos from the era — thick hair highlights and frosted tips were the go-to for many teenage guys during the ’90s and early 2000s. These looks achieved maximum impact with minimal effort.
Bold hair highlights involved adding streaks of lighter colors to the hair, usually done by bleaching or dyeing. The streaks could be subtle or dramatic, depending on the look desired. The biggest mistakes were made in bright colors like red. On the other hand, frosted tips lightened the hair’s ends to create a two-tone look with darker roots and lighter ends. This style was often seen as a way for young men to express themselves and stand out from the crowd. It’s just too bad half the other guys in the room were doing it, too! Read out guide to more prom hairstyles to try!
4. Vests Galore

In the early 2000s, vests became the fashion staple of choice for many young men attending prom. A bold move away from prom suits, vests allowed guys to express their personal style without sacrificing any of the formality. From velvet to satin, patterned to plain, there was a vest out there for everyone. This was also a good way to show off some flair with a pocket square or lapel pin.
Vests were trendy during the Y2K era because they allowed you to mix and match various colors and fabrics to create unique looks that no one else had. Whether it was a waistcoat, cummerbund or full vest, this look definitely made an impression.
5. Hoodies Under a Blazer or Dinner Jacket
The hoodie was the answer for the guys looking for a way to add a dose of street style to their prom look. By pairing a hoodie with a sport coat, young men could express themselves while still looking stylish and appropriate for the occasion. This look was especially popular during the Y2K era, when it seemed like everyone was wearing hoodies with everything.
Though some schools may have frowned upon this look, it’s definitely one that has stood the test of time. It gave young guys a way to dress up without giving up their sense of casual coolness and individuality. The trick was getting that prom tux rental a size or two larger so the hoodie fit underneath. Who knew the humble hoodie could be so versatile?
6. Fashion Scarves
We’re big fans of men’s ties doing the speaking when it comes to formal events like proms, but it seems like the late ’90s and early 2000s had a different idea. During this era, it was common to see guys wearing long scarves draped over suit jackets or tuxedos as an extra accessory. Though these pieces of fabric gave off an air of sophistication and elegance, they aren’t essential accessories. However, scarves were definitely dapper for the few who knew how to pull off the look.
The best way to pull off this ‘90s prom look was to keep the scarf small and simple — like a subtle splash of color or texture — and not go overboard with patterned fabrics or bright colors. Otherwise, you risk looking more like an over-the-top fashion maven than someone who’s ready for prom.
A Final Reflection on Y2K and ’90s Prom Looks
It’s always fun to look back on those who came before us and learn about their interesting fashion choices. So why not take a trip down memory lane and revisit the infamous Y2K and ’90s prom styles like described above. If Y2K or ’90s prom look wasn’t up your style alley, then these pastel prom suit ideas or these stylish prom suits might be more to your liking!