20 Britney Spears 'Street Looks' Of The Past Decade

We all love Britney Spears. Chances are, we all grew up listening to her music and loved songs like "… Baby One More Time" and "Toxic." Maybe we even dressed up like her for Halloween a few times (that schoolgirl look was definitely a super popular costume and even is to this day). We're definitely glad that these days, Brit has made a big comeback and is back to doing what she does best: making fun pop music and performing. Phew, right?!

Over the years, Britney Spears is known for her iconic outfits, from the all-denim look that she matched with her then-boyfriend Justin Timberlake to her all-red leather jumpsuit for the "Toxic" music video. But that's not what she wears on her days off. Nope. It's not even close. No matter how big of a fan we are, we have to admit that the pop princess doesn't always look like the fancy, successful celebrity that she really is. Most of the time, when she's photographed out and about or running errands, she's wearing clothes that we really wouldn't expect to see the star in. Check out 20 Britney Spears "Street Looks" from the last decade that are pretty questionable…

20 Lady In Leopard

Yup, this outfit is for real. At first glance, it kind of looks like Britney is channeling an '80's star or something, at least based on her hair alone. Oh yeah, and her baggy jeans and red sneakers and big pink earrings totally have the style vibe from that decade, too. That's for sure.

This outfit might not be horrible if there only one of these elements were present. These patchwork-style, ripped jeans might be okay with a plain white or black t-shirt or something, and the same thing goes with that hair or those sneakers. But, well, the combo of those elements with that leopard cropped top? Yeah, it's safe to say that's a little bit much, and it doesn't look that flattering or that great.

19 Distressed Denim Don't

There's really no doubt about it: those jeans are not something that ever should see the light of day.

Phew. Now that we got that off our chest, we can say that these jeans are just completely confusing. They take "distressed" to a whole new level. We probably didn't even think that it was possible to have jeans that were quite this distressed. Did we? No, we definitely didn't. It just doesn't seem like something that would ever happen. These jeans are on another level because they not only have rips and tears but they have green stains underneath the knees. Oh man. We're just not even sure what is going on here and we think that anyone would have that reaction if they looked at this photo.

18 Casual But Not That Chic

Like a few of the other elements that Britney has worn, this one is bad because of the sum of its parts. This distressed band t-shirt might look chic and cute if worn with skinny jeans or leggings. That definitely doesn't sound like the worst outfit idea.

It's just that when this t-shirt is paired with green shorts and black and cork wedge sandals, and a green baseball cap to top it all off, it's not the best look ever. Oh yeah, and those red-tinted sunglasses don't do the outfit any favors, either, and neither does her ponytail that she's threaded through her baseball cap. This really isn't her most flattering look and while it's better than full-on sweats, there are a lot of other outfits that she could have worn.

17 All Sweats All Day

Yup, it's been confirmed yet again: this pop star loves her sweats. Sure, she's wearing black leggings here, so at least she's not wearing a sweatshirt and sweatpants (this time, that is). But she's still got a sweatshirt on and boots that look more like slippers, so there's that.

At least she's consistent? Yeah, let's go with that. Let's try to be positive. Again, there's nothing super wrong with this red sweatshirt, or with black leggings, so this outfit is another example of when you wear a bunch of items of clothing together and they just don't work. The red sweatshirt with the pink tank top with the leggings with the boots just look too messy to be fashionable. That's really the only way to put it.

16 Plain Jane

The problem with this particular outfit is definitely that it's just super plain. It's not something that we would expect a pop star (or any celebrity of any kind) to put on and go outside in. Also, the pants are massive, so there's that.

Seriously, though, it's hard to imagine pants that would be baggier than these. They don't look comfy because wouldn't you find it tough to walk in them (or even move in them at all)? That's a serious question. It just doesn't seem like these would be that comfortable, and as we can see from some of these other looks, that's what this pop star loves. Her short bob hairstyle and plain long-sleeved t-shirt also don't seem stylish enough for a pop singer.

15 What's Happening?!

This is a really, really bad top to wear. There's no other way to say it. But wait. Is it even a top? Is it a… poncho? Maybe? Not sure? Okay, let's go with poncho.

The truth is that the rest of the outfit wouldn't have been that stylish without the poncho situation since those pink boots aren't flattering and the jeans are too baggy and it looks like she's wearing too many tops layered on top of one another. It's all a bit much. And bright pink is a tough color to pull off for boots, let's just be honest here. But with the poncho… well… that really puts this outfit over the edge. We don't think that this is flattering and that's all there that there is to say about it.

14 Is That You, Brit?

If we didn't know that this was a picture of pop singer Britney Spears, it would be easy to say that this was a random person and that we didn't know that it was her. It really doesn't look like her at all.

Between the ripped black leggings and tall fuzzy boots and two-toned t-shirt and messy hairstyle, this isn't a look fit for a pop star. It just isn't and we're sure that anyone would agree with that statement. We would say keep the leggings and get rid of the other elements here and this outfit would be okay… because it would be a totally different outfit, which seems necessary. This just isn't her best look. It doesn't seem like it would look great on anyone though, whether they were a celebrity or not.

13 Just… Not Good

Just like the above photo (and most of the photos on this list, let's be honest), we wouldn't know that this was Britney Spears. The super baggy sweatpants, running shoes, and tank top don't exactly scream pop princess. They don't scream celebrity of any kind, even.

It's one thing to be comfortable. We get that. But that's why athletic wear has become such a big thing. We all want to be comfy and cozy when we leave the house and go about our day, but we want to be stylish and chic, too. And the truth is that you can't be stylish and chic when you wear something like this. You just can't. That's not how you works. You can absolutely be comfy -- you just have to throw on leggings and a cute top. It's pretty easy.

12 Matchy Matchy

What can we say about this look? Well, at least she matched her casual tank top to her casual baggy shorts and is wearing running shoes. It's not like she chose to wear running shoes with a really fancy, elegant outfit.

Honestly, most of us probably did a double take when we saw this image and weren't sure that it was really the pop princess herself. But it is. She tends to favor casual outfits like this one when she's running errands, and, look, of course she can wear whatever she wants. This is just not the most flattering outfit that she could have chosen. That's all we're going to say on the subject. Oh yeah, and we're not sure why her ponytail is so many different shades. We'll say that, too.

11  At Least She's Comfy

There's a great joke on Seinfeld where Jerry and George are discussing what it means when someone wears sweats outside of their home and the conclusion is that if you do that, it means that you've given up. We know that Brit is still stylish when she's performing or heading to events, and we know that she's still rocking her awesome career, so why is she wearing an outfit like this one?

This honestly looks like something that we would have worn back in our college days. You know, when we were super hungover and were walking to class or the dining hall. Real clothes just seemed too uncomfortable and like too much effort. Seriously though, these sweatpants are really baggy, so can they really be super comfy?

10 Out And About

This outfit might have been okay if Brit had paired this sweatshirt with plain black leggings or yoga pants. Or maybe jeans. And had lost the huge boots that look more like slippers than actual shoes. Wait, maybe those are slippers. We're not sure. And, honestly, we should be able to tell, right?

The sweatshirt alone is kind of cute and not the problem. It's the fact that this sweatshirt was paired with baggy shorts and slipper-like boots that is really confusing. It just isn't the best look and we think that she could have worn something else to run errands in. Or do whatever it was that she was doing that day. Also, let's face it, those shorts are super short. Maybe a bit too short.

9 Coffee Run

If Britney had worn this outfit to work out in, whether she was heading to a workout class or going for a run outdoors, we would have said that it was fine. It really does look like a workout outfit. We don't always feel like wearing something super tight and chic when we're breaking a sweat, right? Sometimes we just want to be comfortable, and if there's one thing that we can say about this particular outfit choice, it's that it's comfortable. Or at least that's what it seems like.

Brit wore this to grab some iced coffee and we think that if she had worn yoga pants or leggings, it might have saved the outfit. But this baggy tank top (with her bra strap totally visible) and baggy shorts just aren't super flattering.

8 A Bit Confusing

What is that?! Is it a sweater or a shawl or a blanket or what? No, really, we're not quite sure. Besides being super massive and way too baggy, it also has holes in it. So there's that.

It also looks like the pop star is wearing grey sweatpants with this purple top and this sweater (or whatever it is), and that's pretty confusing. It would be one thing to pair a purple t-shirt with grey sweatpants. That's not the craziest, most out there outfit choice. But wearing those together with this top is just a bit much for us and definitely not something that we would expect to see a pop princess wearing. Her hair is also in a really high ponytail and doesn't look like it usually does.

7 Caught In Her Web

This blue poncho with a white spider web pattern on it is just a lot for us to handle. We might need a minute to think about this.

Okay. We're honestly not sure where to start with this. We don't think that it would be that flattering on anyone, let alone a famous celebrity, so that's where we stand on this item of clothing. Britney looks really uncomfortable here and has a strange smile on her face, almost as if she's forcing herself to look happy. Cheesy as it might sound, smiling really is one of the best accessories. Okay, that definitely sounded cheesy, but nevertheless, it's true. If we can gather one thing from this collection of outfits, it's that she loves comfort, but a plain sweatshirt would have been better.

6 Breaking A Sweat

Do we think that Brit was headed to a workout class in this photo, or had she just finished an epic sweat session? That would absolutely explain this outfit choice. Otherwise, it's a bit confusing. Because this really does look like a workout outfit.

It's hard to know where to start when discussing this outfit. There's the t-shirt that is so baggy that it's falling over one shoulder. That style looks '80's inspired and not like something that is really stylish these days. The pink shorts are not that flattering but would make sense if she was getting her workout on. We're not sure if that flash of purple is a bra or tank top but either way, it's hard not to think that the overall effect is pretty messy.

5 Not So Sunny

It's a sunny day and Britney is hanging out, looking fit and toned and gorgeous in a ruffled tube top and black shorts and wedge sandals. Because that's the thing about this image: the outfit is not that great, but she looks great. That's not something that happens all that often, right?

Those black shorts are not terrible at all and would look chic and cute with literally any other top. Literally anything. But this striped pink and white tube top with ruffles is just not a good look… and wouldn't be good for anyone, pop star or not. That's a statement that we all probably feel very strongly about. It also looks like it's way too low and is about to fall down completely, which is never a good thing.

4 Covering Up

We get that you might want to cover up when you're wearing shorts (or a short skirt, it's tough to tell what from this photo) and a t-shirt and sandals. Most people would probably choose a jean jacket, blazer, or sweater. There are tons of different options and all of them would be a lot chicer and more stylish than this strange cover-up.

Sorry, but it's a very confusing style choice. It doesn't match the rest of the outfit and doesn't even really match Britney's usual style -- well, from what we can tell from these outfits, that is. She definitely likes to be comfortable but this cover-up doesn't look particularly cozy or warm. It also looks like there's a stain on the front of her grey t-shirt, and we're not sure what's up with that.

3 Stained Sweatpants

Okay, now this is a pretty rough outfit. Sorry (again) but this just isn't something that you should wear out in public. And that goes for anyone, pop star or not.

The white sweatshirt is way too long and big, the purple sweatpants are way too baggy and long (and, oh yeah, there's the fact that they're purple which is not the best pant color), and the brown Uggs look more like slippers than outdoor shoes. Let's chat about the most obvious part of this whole ensemble: the big red stain on those sweatpants. Yes. That is real. Here's the thing: you can't leave the house in stained sweatpants. Or, really, any item of clothing that has a massive, obvious stain on it. It's hard to believe that a celebrity would really go outside in something like that.

2 Summer Day

We can tell that Britney was probably going for a nice, easy breezy summer look with this ensemble, but it didn't really work out that way. Instead, it's a confusing mix of black capri leggings, a white lacy long top that looks like a style from a few decades ago, and short boots that don't match the season.

This is the kind of long top/dress that we would wear when we were pre-teens and teens, right? It honestly looks very old-fashioned and like it's from another time. It's also not the most flattering thing ever because it looks like something that you would wear as a cover-up on a beach vacation. It's just hard to say that this whole look works together. If she had lost the leggings and the boots, the dress would have been way too short, but at least it would have seemed more summery.

1 Um…

There are really no words for this particular outfit. No words.

Okay, okay, maybe we can muster up a few. Basically, we're super confused about this whole thing. Why is Britney wearing this? Why did she choose to wear such a massive red skirt in the first place? It's not only huge and baggy but also very long. We're also not sure why she would pair it with a short top like this one, especially something that is an off-the-shoulder style. She's also wearing what looks to be a pearl necklace, which is another confusing element, and a strange fedora. Oh wait… and she's barefoot. Why is she barefoot? Why is this happening? We really have no idea and we really just can't even with this outfit.