OB Style Inspiration: How To Dress To Heirs Holding Y2K Themed End of Year Party

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With the year coming to an end in less than 2 weeks, Holiday parties continue to make grand strides/waves and the latest already on its way to that feat is Heirs Holding’s Y2K themed end of the year party.

As you already know, retro fashion isn’t going anywhere anytime soon and if you’re a 90s or 2000s baby you’d probably remember it’s fashion pretty well. But if you don’t know a lot about that year or have just forgotten, here’s what you need to know about 2000s fashion to put together the perfect look for Heirs Holdings party or any other retro event.

Many clothing trends in the 2000s were born out of globalization, the rise of fast fashion. In other words, affordable clothes based off runway designs were trendy along with celebrities’ growing influence as style icons. As with all decades, looks and trends varied as the ’00s went on, so if you’re looking for an outfit to fit your style, make sure that the style is from the right time period that you’re most comfortable with.

Technology had a huge impact on fashion in the early 2000s. The color palette was filled with shiny black tones and reflective metallics. Popular looks for women included mesh or handkerchief tops, box-pleated or leather skirts, shiny pants, and sparkly shoes. For men, Y2K looks usually involved leather jackets, a statement dress shirt, and chunky shoes.

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Casual clothing and leisurewear were the other big trends of the early 2000s. Denim became a staple for men and women, going beyond jeans to shirts, jackets, and hats. If you’re putting together a casual style for women, think crop tops, hoodies, low-rise flared jeans, cargo pants, daisy dukes, jean skirts, off the shoulder tops, ribbed sweaters, with platform sandals, Ugg boots, or sneakers. Common looks for men included, distressed denim, cargo pants, tracksuits, rugby or polo shirts, flip flops, oxford shoes, and sneakers.

As the decade went on, 2000s fashion began to take cues from 1960s bohemian looks. Yoga pants, low-rise jeans, cowl-neck shirts, peasant tops, capri pants, cropped jackets, and dresses over jeans were popular outfit choices for women. These were often paired with accessories like chunky belts, aviator sunglasses, jelly bracelets, ties worn around the neck or as belts, ballet flats, and platform boots.

The 1960s revival looks were also popular with men. Outfit options included light wash bootcut jeans, cargo shorts, classic rock t-shirts, fitted cowboy shirts, henleys, polos with popped collars, and seersucker suits.

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Many styles from the early and mid-2000s carried over to the latter part of the decade, with a few exceptions. For women, crop tops were replaced with camisoles and miniskirts gave way to babydoll, bubble skirt, and sweater dresses. There was also a 1980s and 1990s revival that reintroduced neon colors, animal prints, geometric shapes, light denim jeggings, and ripped acid washed jeans that were worn with gladiator sandals, ballet flats, and headbands. An oversized look also started to gain popularity.

Men’s late 2000s fashion was a mix of 1950s and 1980s throwbacks, with letterman and black leather jackets, overcoats, slim cut jeans, flannel shirts, and V-neck sweaters. These were often paired with dad hats, wayfarers or aviators, motorcycle boots, Converse, Vans, or sneakers. The men’s power suit was also updated from the ’80s to have more a slim tailored cut.

Below are 2000s fashion broken into groups.


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Many rappers influenced fashion with their own clothing lines in the 2000s, including Jay-Z, Diddy, Nelly, and 50 Cent. Many looks included baggy jeans, tall t-shirts, sports jerseys, velour suits, bubble jackets, and puffer vests paired with headbands, sweatbands, Timberland boots, and sneakers like Adidas Superstars or Nike Air Force 1s.


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Streetwear is often brand focused casual clothing, like jeans, tees, and sneakers. In the late 2000s, popular streetwear styles included distressed skinny jeans, loose fitting tops, loose or fitted tracksuits, track pants, hoodies, graphic t-shirts, and vintage thrift shop tees. Sneakers were an important part of the look, especially retro Nike Air Jordan’s and Adidas Yeezys. Shoulder bags were also a popular accessory for men.


Emo fashion trickled into the mainstream in the mid-2000s and took cues from goth and punk styles. Outfits were often all or mostly black with skinny jeans, band t-shirts, studded belts, and checkered Vans. No emo outfit was complete without the right hairstyle, most common were choppy cuts with long side-swept bangs dyed black, platinum blonde, or a bright color.

If you wanted to be comfortable yet fashionable in the early 2000s, all you had to do was throw on your favorite tracksuit. Everyone from Britney Spears to Beyoncé and Eminem to Diddy were in on the tracksuit craze. They were often brightly colored and emblazoned with rhinestone logos and phrases. It was also popular to mix track pants with dress clothing and designer shoes to elevate the look.

See more looks below.

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