How To Dress Like ‘90s Britney Spears

Ahh, the year 1999. It was a simpler time, wasn’t it? Cell phones were still a gadget of wonder, computers were still the size of your family dog, and Britney Spears had just released her first album. A lot has certainly changed — back then, Spears' first album was more down home Disney Channel than anything else, and — though I love songs like "If You Seek Amy" and "Work, B**ch" — there was a certain charm to it that totally deserves to be paid homage to. Like, say, through a '90s Britney Spears Halloween costume this Oct. 31?

If dressing up like '90s Spears is what you were thinking for this Halloween, don't shy away from the idea: The ‘90s are back in a big way and so is Spears, which means we can start recycling trends, listening to all of her '90s music unironically, and wearing all of our old clothes that have been out of style for decades.

I’m going to go out on a limb and say that there is probably a good number of you who have already dressed up like ‘90s Britney Spears in your life — and that was probably back in the 1990s. But, just in case you didn’t, or you were more of a Shirley Manson/Fiona Apple type back in the day, you've come to the right place. Here is everything you need to dress exactly like Britney Spears circa 1999:

1. Crop Tops

Whether you go for the honest crop top or just tie a longer t-shirt into a knot, baring your midriff was a requisite part of being Britney Spears in 1999. And, like, in general. Forever.

This piece from American Apparel is absolutely perfect in silhouette, color, and fit. Just how Spears would have worn it!

Crop Top, $26, AmericanApparel

2. Ultra Low-Rise Jeans


They can be pants or shorts — pick your poison. But, they have to be so low that lifting your hands above your head or bending past ninety degrees would be a dangerous decision. Weren’t the ‘90s SO FUN?

These Rock and Roll Cowgirl jeans from Horsetown Western Stores definitely fit the bill.

Rock&Roll Cowgirl Jeans, $30, Amazon

3. Pink Everything

Pink shirts, pink shoes, pink hair accessories, pink cheeks, pink skirts, pink pants... just everything pink. It will really up the wholesome factor.

In 1999, Spears was still sporty: She rocked a simple hair cut, and was often seen in track pants and sneakers. These H&M sweatpants are totally something she would have worn back in the day.

Pink Sweatpants, $10, H&M

4. Thick-Soled Sneakers/Sandals

Depending on the weather where you are, you might want sneakers or sandals. Either way they have to be thick-soled... practically platform.

Skechers is a dependable brand — check out these shoes from Amazon.

Skechers, $36, Amazon

5. Bangs


Like the short, girly kind you wore when you were thirteen.

If you're not willing to go for a full-out cut and dye job, try this wig from kekeshop on Etsy. The face framing front layers give it the perfect '90s touch.

Basically, you want to dress like who you were in 1999, because back then, Britney Spears was still trying to pretend to be just like us. Throw in a t-shirt, a pair of bootleg jeans and you’ll be all set.

Image: Giphy (2); American Apparel; Horsetown Western Stores; H&M; JCPenney; kekshop