Here's How To Do '99 Style, The Britney Way

It's been about 15 years since Britney Spears unleashed "...Baby One More Time" on us and changed our teen years forever. Since that unforgettable day, we've watched our girl go through good times and bad. We've followed the move from Justin to K-Fed (#TeamCharlieEbersol), rooted for her through her (many) issues, and, most importantly, paid close attention to her ever-changing fashion choices.
So, in honor of her 33rd birthday, we've pulled together some of her most iconic looks ever (really, a gift for ourselves). What may have seemed borderline crazy at one time is now starting to seem, well, on-trend — including this editor's personal favorite, the all-denim outfit (matchy-matchy denim wins). Click through to see the modern versions of our favorite early-Brit looks. And, tell us your fave in the comments. Happy birthday, Brit.

Like this post? There's more. Get tons of style secrets, insider shopping dish, fashion news, and more on the Refinery29 Fashion Facebook page!
1 of 20
The Cropped Jersey

Need a way to step up your crop-top game? Put a sporty twist on it. Keep it modern with high-waisted boyfriend jeans — not Britney’s beloved low-rises.
2 of 20
The black-white-and-red look makes for a graphic upgrade to the cropped jersey.
3 of 20
Loose-fitting, high-waisted boyfriend jeans bring the outfit out of the aughts and into 2014.
4 of 20
These Acne boots elevate the entire look, both literally and figuratively.
5 of 20
The All-Denim Outfit

Granted, this iteration of a Canadian tuxedo isn't making a comeback (yet), but the 2000s power couple was onto something. Add a '90s-inspired choker to your denim-on-denim number, and you've got the perfect, fashion-forward #TBT outfit.
6 of 20
Sure, the '90s were all about tattoo chokers, but for a fancier occasion, try an embellished version.
7 of 20
This denim pencil skirt is one of our favorite throwbacks (especially because of those adorable little animals).
8 of 20
Pair the pencil skirt with a chambray shirt in a different wash, and you have a current, sleek take on Britney and Justin's all-denim-everything styles.
9 of 20
The Mechanic Jumpsuit

Floral rompers and slinky jumpsuits are all well and good, but when it comes to something a little more lax, you can still take a note from teenage Britney and sport a classic, boxy one-piece.
10 of 20
A mechanic-esque jumpsuit (rather than one in electric yellow) is cool and forward.
11 of 20
Master the perfect high pony with an easy-to-use tie.
12 of 20
Good news: Timberlands are just as cool now as they were 15 years ago.
13 of 20
The Pleated, Plaid Skirt

The collegiate prepster style is on its way back. Tartan fans, rejoice!
14 of 20
A white button-up is a staple, no matter what decade it is.
15 of 20
A half-pleated skirt looks a little more grown-up than Brit's schoolgirl getups of days past.
16 of 20
A metallic heel gives knee-high boots a modern twist.
17 of 20
The Silk Slip

A sexy, feminine slip never goes out of style — and you can pair it with current pieces for an update.
18 of 20
A plain-and-simple slip dress is perfect for a night out.
19 of 20
Strappy sandals with slim heels can breathe new life into any party outfit.
20 of 20
Why go for basic studs when you can choose a pair with a little extra something-something?

Shop your inbox!

yay! get ready for the good stuff!