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There isn’t a household in America who hasn’t heard of Britney Spears. Millions of us grew up with this pop icon’s music, and the star is giving iTunes a run for their money. You might love Britney, you might not–but either way, you know her. “Hit Me Baby Me One More Time” made this music mogul rich beyond belief. $34 million is the figure Forbes reported Britney as earning in 2017, and that’s pretty good going when you grew up in the trailer park.
Sweetheart looks and a girl-next-door smile have won us over by the millions, and we literally know the words to all her songs. Britney’s eye-popping tour outfits can easily rock the internet, but fashion sense doesn’t always come easily to this star. Britney has worn some iconic looks (having a snake wrapped around you on stage will do that), but she’s also raised a few eyebrows. Clashing colors, stained sweats, and a very #nomakeup vibe is her go-to street style, although Britney can totally turn it up a notch with alluring mini dresses. If you grew up worshipping Britney, you’ve probably seen her style evolution. At one extreme, Britney can rock that body for a sensational look. At the other extreme though, she’s dressing like she never left her trailer. You’re in for a ride with these 10 pics of her million dollar style, but watch out for the other 10 where she never left the trailer.
20 PRETTY IN PINK
This is one the haters can choke on for a long time. Britney couldn’t look more perfect in this pretty-in-pink shot that she shared with fans in 2017 on Instagram. Britney isn’t scared of rising stars like Kylie Jenner (at least Britney is actually famous for her creativity and talent).
The mom of two has kept a super fit physique thanks to her energetic dance routines, and this pic was out to slam anyone who disagrees.
She looked every inch the pop icon here, and everything about it says “million dollar look.” Britney keeps it real. She might live in a $9 million Californian mansion, but there are no airs and graces when it comes to this girl. She’s pushed onwards and upwards from her Louisiana roots and we challenge anyone to say she doesn’t look amazing.
19 LITERALLY LOOKING LIKE A DIFFERENT PERSON
The sweater might say “Peace Love World,” but the look says “Global Mess.” This 2017 shot of Britney didn’t see her looking her best as she stepped out in Los Angeles. Drawstring sweats and an off-the-shoulder look can be done right, but if you’re a celebrity, seriously, try to make the look more put together.
Britney might have been spotted in a Mercedes-Benz SUV later that day according to The Daily Mail, but this outfit seems a bit more appropriate for her past.
Britney looks worn out, stressed, and definitely in the need of some beauty sleep here.
18 BACK TO LOOKING LIKE A MILLION DOLLARS
It’s looks like these that explain why Britney is considered a style icon. This glittering designer Roberto Cavalli number showed us the Britney we love, and she looked perfect. To be fair, it was nearly ten years ago, but the 2009 Teen Choice Awards would have felt a bit empty without Britney. FYI, she’s dressed head-to-toe in classy stuff here.
The Jimmy Choo shoes she wore to match retail at around $1000 a pair, but when you’ve sold over 100 million records, what’s a thousand bucks here or there?
Britney’s blonde locks and million dollar smile just say “gorgeous,” and this pic totally earns its high ranking.
17 NOT A FAN OF DOING LAUNDRY
Looking a little less glamorous in her signature sweatpants here, Britney is a girl who knows how to dress down. This isn’t the first time she’s stepped out in stained clothes, either. In 2013, the singer headed out for groceries on a sunny Sunday morning, and something about this look doesn’t exactly say “buying detergent.”
Britney might be wearing shades that say “celebrity,” but this look needs some serious work. The oversized sweater looks like something The Dollar Tree couldn’t get rid of. Sure, Ugg boots are stylish, but when they’re drawing attention to your stained sweats, you need to get a grip.
16 ANGEL IN WHITE
Well, doesn’t Britney look like an absolute angel here? Britney made a wise choice with this 2000 Grammy Awards dress, where she managed to look sophisticated and sweet all at once. Britney has made some seriously questionable fashion choices (particularly at award ceremonies), but she really nailed this outfit.
Of course, she was still really young here, but at 37, Britney still has one of the most enviable looks in Hollywood.
It’s really rare to see Britney in a full evening gown, but clearly someone had convinced her that covering up can still be cute.
15 THE FAMOUS DENIM DUO
What were you thinking, Britney? This one takes us back to 2001, when Britney and her then-boyfriend, Justin Timberlake decided to make a statement at the American Music Awards.
Celeb couples have a thing about matching outfits. David and Victoria Beckham did it in leather Versace before they were married, but this one is a bit of a joke.
The duo appeared in a his-and-hers denim display that probably cost a ton of money, but where’s the class? Aren’t award ceremonies supposed to be your chance to look your worth? If you’re #TeamBritney all the way, though, you can buy a t-shirt of these two wearing the outfit. The “never forget” tee will cost you $152.47, but to be honest, we’re not sure we need the reminder.
14 WHO SAID BRITNEY CAN’T BE CLASSY?
Just wow. Britney showed the world she can be one classy lady with this insanely classy pantsuit back in 2014. The occasion? The launch of her own lingerie collection in Germany.
Britney paired the chic look with a totally appropriate bob hairdo, and she sure did turn heads.
You can tell from the pic that these clothes cost big bucks, but unlike other celebs (who take the opportunity to show too much skin), Britney owns her feminine charm. Then again, the next pic has us wondering where that went…
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13 THE PARKING LOT LOOK
For every dazzling little number Britney wears, there seems to be a set of sweatpants waiting for her, and Britney just doesn’t give up. This pic may be from Kim Kardashian’s home territory, Calabasas, California, but the look would probably be more fitting for her trailer park days.
Britney is flashing us that taught stomach, but the glam look has a long way to go. Celebs drop thousands on a full fleet of stylists, and they even get the world’s top designers flown out for dress fittings. Why Britney insists on dressing like she can’t afford nice clothes, we have no idea. Thoughts?
12 FRESH AS A DAISY
When you look like this, you get to ride around in a chauffered vehicle. Britney stepped out in style in 2012 at the US X Factor auditions in Kansas City, and boy did she make waves.
Proving that 30 is the new 20, Britney looked fresh as a daisy in this summery dress, and she didn’t break a sweat, despite the Kansas heat.
According to TMZ, she did have a bit of a wobble in those high heels, but she quickly found her feet. That’s kind of Britney’s metaphor in life, right? She gets hardship thrown at her (like losing custody of her two kids), but she always comes out the other side. Another winner look from a winner starlet.
11 LEOPARD PRINT DONE WRONG
No, this wasn’t the morning after Halloween. Britney decided to step out in this clashing number to the set of singer, Iggy Azalea’s music video. Ironically, the track is called “Pretty Girls,” but Britney sure is pushing the boundaries of her natural beauty here.
Fake tan galore, distressed denim, and grandma shoes aren’t sending us the best #squadgoals. They’re definitely not giving us fashion envy.
Britney has collaborated with a ton of music artists. She’s teamed up with Madonna and Will.I.Am. With this outfit though, we’re thinking it’s very much “Will I Won’t.”
10 TALK OF THE TOWN
Britney sure does know how to light up a talk show. It’s hard to believe Britney was already 34 in this 2016 pic of her on the UK’s The Jonathan Ross Show. The show gave us the inside scoop on how Britney really feels. “I know it sounds boring,” she said, “but I’m not this crazy go-out girl. I cook. I like rice, that’s my favorite thing.”
Britney is often spotted at the grocery store, and the paparazzi even found her shopping list. The Daily Mail reported that she had milk, eggs, and Captain Crunch, but Britney couldn’t spell Cinnamon Toast Crunch or mayonnaise. Oops.
9 GOING FOR THE WRONG FLORAL PRINT
Um, very little about this look says “tasteful.” Britney kind of looks like she’s tried here, but the most she’s managed is a giant fail, and we don’t know where to start. First, a multi-millionaire should be able to afford a hair stylist. Oh, and a make-up artist.
Britney’s bright red lipstick and bleach blonde hair isn’t saying “Hollywood royalty” here, nor is that dress.
To be fair, some of Britney’s outfits are so amazing, she’s literally wiping the floor with the competition. But this floral print fail wasn’t one of her successes, and it’s just another reminder of her trailer park roots.
8 GIVING THE KARDASHIANS A RUN FOR THEIR MONEY
What, you thought you need to be a Kardashian to look glam? Three words: proving you wrong. Longtime Britney fans will of course know that she also absolutely loves the color blue.
Flawless hair and a boss attitude make this one of Britney’s best looks, and she’s owning every second of it.
Britney’s cheeky “Toxic” video saw her in a powder blue number on an airplane, and she’s worn all shades of blue to award ceremonies and appearances. Of course, for every cute dress Britney wears, there’s a disaster outfit around the corner…
7 NO WORDS FOR THIS LOOK
One minute, she’s winning Grammy awards. The next, she’s back the parking lot. In a way, it’s good to see a celeb keeping it real–yeah, she’s a mom. She goes grocery shopping. Her kids, Sean Preston and Jayden James have a real mom, but what about one who looks good? You’d think being mega-rich would make Britney want to put Walmart firmly behind her, but this is one star who won’t quit.
It’s one more parking lot look for Britney here as she was photographed outside a grocery store. She’s carrying her signature iced coffee, and it looks like she’s bought some gifts for the kids. What about buying some new clothes, Brit?
6 #INSTA READY
19.2 million of us follow Britney on Instagram, and it’s pics like this that prove why. She captioned the photo with, “Going out tonight! Found my red dress!!!” It’s definitely showing her best side. Wait, didn’t Britney just say in an interview that she likes to stay home and cook rice? Given how much effort she’s put into this look though, we’re letting her off the hook.
She has let her hair down, is actually wearing appropriate clothes, and hey! She does own a hairbrush after all. Britney looks sensational, but it’s the last good look before we go back to disaster city.
5 NOT ALL HER DRESSES ARE THE RIGHT CHOICE, THOUGH
In this look, Britney is definitely trying, but she isn’t succeeding. Photographed in the parking lot as usual, she’s back in Calabasas, California here, although she’s sticking out like a sore thumb. At the time, she was dating Jason Trawick, although this was 2010, and a difficult time for Britney.
The pink dress might be cute, but the mismatched handbag and messy hair are nothing like the Instagram pic you saw at the top of this list. Another misstep from Britney.
Britney was facing legal troubles from her security team according to People, and she’s definitely showing the strain.
4 GLITTER GODDESS
If there’s anything Britney loves, it’s glitter. Her revealing performance outfits are layered with the stuff, and who can blame her?
As long as it’s strappy, tiny, and glittery, Britney will go for it, and she looked great in this little number.
Of course, it’s that winner smile that makes her stand out from the crowd here, although Britney hasn’t quite mastered painting it on all the time. Some super embarrassing pics of her weird facial expressions show a completely different person, but we’ve already figured out that her two styles are worlds apart.
3 THE SAUNA SUIT
From the woman who managed to wow us in a white pant suit, we literally have no idea what was going through Britney’s head here. While other celebs hang with their squad in oceanfront restaurants (or on yachts), Britney seems to prefer the parking lot. According the The Daily Mail, there was a purpose behind this look. The “sauna suit” she’s wearing has been explained by Shape House, an LA spa. Apparently, the material helps the body “sweat out toxins.”
Seriously, people. You have celeb clients with $20 million mansions. Was it so hard to put a little style into it?
2 LADY IN LACE
Definitely proving she’s still got it, Britney looks a million bucks in this little black dress. Lace paneling gives her a ton of class, plus she actually looks like she means business. She might have songs like “…Oops I Did It Again!” but Britney is a savvy businesswoman. Britney has released several successful fragrances, and if having $185 million to your name on your 34th birthday doesn’t say “success,” we don’t know what does.
This pic wasn’t taken on her actual birthday, although she has treated herself to some ice cream. Totally deserved, particularly with that enviable body.
1 PRETTY MUCH SUMS HER UP
Britney may have spent half her time on this list looking glammed up, but she’s got an equal number of pics that say “never left the trailer park.” Britney’s refusal to give up her tanks and sweats haven’t been matched by anyone in Hollywood. Given the #talktothehand vibes she’s giving us here, it looks like she doesn’t care. Britney has given us nearly two decades of her gorgeous smile, glittery dresses, but also her less than perfect style choices.
Which look do you like best? Do you care that she walks around with stained sweatpants? If you’ve got a friend who needs some serious fashion advice, hit share and make sure you friends see this. Of course, there’s always the chance they’ll pick up the wrong kind of inspiration…
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