The beauty and style evolution of Britney Spears, from those iconic pigtails to crop tops galore
Do you remember where you were when you heard your first Britney Spears song?! For many of us, Britney was a force from childhood on, and imagining a world without her is near inconceivable—she’s set the course for so many pop stars and has inspired countless fashion trends. Let’s be honest, very few people can pull off Canadian tuxedos or chunky blonde streaks with the same glam gusto as Britney, and that’s precisely why she’s iconic.
Since our pop princess’ birthday is today, we thought we’d take a long stroll down memory lane to gaze upon her beauty evolution the past few decades. She was just a baby teen when she first hit the spotlight in the late ’90s, so her looks have true range. She came out of the gate in pigtails, a sweater and lip gloss for “Baby One More Time”, but fully grew into a metallic smoky eye and platinum hair by the time she made “Toxic.”
Britney’s fashion and beauty changes have certainly not been limited to the costumed world of her music videos, she’s played around with a lot of makeup and clothing looks in her personal beauty journey. Below, 16 of Britney’s best beauty looks in celebration of her birthday.
Look at what a baby she was! Our girl had just blown up this year for “Baby One More Time” and she is fully glowing with her zigzag hair part, lip gloss, and natural makeup. We’re pretty sure Britney’s responsible for the uptick in teen girls zigzagging their parts in the late ’90s and early 2000s.
Britney fully brought her wholesome vibes to MTV’s “Big Help Concert.” Her iconic pigtails, the sweater, the blush, and lip gloss are all very late ’90s preppy.
Here, we see Britney going full “lady in red” with her monochrome, cropped look, and she’s still minimal on the makeup and this time rocking a middle part—which is almost more bold than the zigzag.
This is not the point, but can we talked about how jacked Britney looks here?! We have full faith she could dance up a storm AND fight a creep if needed. While her makeup and hair styling was still fresh and natural at this point, she started playing with bold style statements right away, thus the pants straight out of Zenon.
Britney welcomed the new millennium by fully leaning into her gaudy side, and it totally worked. Her makeup is more pronounced here, with visible blush and a powdery blue eyeshadow. Plus, she’s fully rocking a silver glittered crop top which is a true fashion power move if we’ve ever seen one.
After a couple of years in the spotlight, Britney fully embraced edgier looks both on and offstage. Here, we see her with stylishly tousled hair (although she IS mid-dance move), and a glitter encrusted bikini-style top and flares. She was not messing around with this lewk.
We would be completely remiss to not include photographic proof of Britney wearing a fitted orange waist coat with a bra, a feathered orange trilby hat, and an equally ornate choker. There is SO much happening in this outfit, and by now, Britney had fully committed to her bold eyeliner and shimmery eye, so she was absolutely the right person to tackle this outfit.
Britney has always been good at evolving, but also allowing herself to revisit precious looks. This butterfly dress feels like a return to her preppy teen origin, although she keeps the bold eyeliner and the silvery-white eyeshadow. It’s an updated return to her roots.
She truly blessed the world when she decided to go full leather daddy with her fashion. This leather one-piece, detailed gloves and hat feel like a costume from a Kenneth Anger film, and it works. Britney is one of the rare people who can effectively pull off a wide variety of hats, and that’s a gift that shouldn’t be squandered.
While Britney’s hair has consistently stayed blonde throughout the years, she went through phases of styling it, tousling it, straightening it and even curling it. In the early 2000s, she rocked razor-straight hair a lot, which can be seen here. Her makeup style had really bloomed by now; the bold eyeliner was usually combined with a metallic eyeshadow, as well as blush and a tinted gloss.
Britney’s ponytail walked so that Ariana Grande’s ponytail could fly. But truly, here her hair game was extra on point—her color is peak platinum, and she has razor-straight strands framing her face with a wrapped ponytail to truly pin this look in the early 2000s. We also have to point out those earrings.
Can we take a good long moment to just appreciate this jacket situation?! We can’t tell if it’s a kimono or just a deeply ornate golden suit jacket, and honestly, either one is doing the work. Naturally, Britney wore equally loud earrings and has her gray smoky eye and eyeliner intact. But here we see her in a rare bold lip—in her earlier years she often wore a tinted gloss, so a deep red was a departure.
13New Years Eve 2007
This is truly Britney at her core. Her hair was super long here and fully blonde, she has her bold eyeliner and shimmery eyeshadow, and a tinted lip gloss to tie it together. But naturally, she was not one to go safe with an outfit, and is fully showing leg in this sweater dress.
BRITNEY IS BACK, BABY. Sorry about the caps, but that’s what this photo screams for us. She is truly embracing her hat-wearing abilities here with a full-on top hat, a mesh crop, pleather pants, and stiletto boots. She’s got her classic makeup: the peachy blush, tinted gloss, bold eyeliner, and shimmer eyeshadow, and she looks ready to tear up the stage.
It’s rare to see Britney wearing full curls, which is unfortunate because she looks super cute in this hairstyle. She’s fully channeling freaky, circus vibes with this outfit, and we want those lace-up boots, ASAP.
Britney got bangs. Throughout the years, she often had baby hairs or tapered strands framing her face, but getting full-on bangs was a move. Here, both her makeup and fashion is paired down for her interview with Jay Leno, she’s got the eyeliner, a little eyeshadow, and a healthy tan.
She’s got a very voluminous hairstyle, and it looks like she traded in the bangs for a more swept back look. This evening dress is trés chic, but we really see Britney’s signature boldness in the golden shoes.
The ponytail is back here, and she went all out by coloring the ends powder blue and green. Between the hair and the skintight golden dress, it’s clear that Britney’s iconic boldness is here to stay.
We are getting some serious Carmen Sandiego vibes here, and it’s giving us some true childhood flashbacks. This is yet again, another prime example of Britney completely wearing the hell out of a hat.
Look at our birthday girl, fully thriving and still killing it. As you can see, even now Britney still has the (super long) signature blonde hair, the bold eyeliner, and the cutest smile. Happy Birthday, Britney!