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15 Fashion Looks That Prove Jennifer Aniston Is Still A Bombshell (And 10 #FashionFails That Make Her Look Like An Old Maid)

When it comes to Jennifer Aniston, she not only comes off as a girl next door but she also has some pretty great fashion sense. We’ve rarely seen her in fashion-nightmare lists. In fact, we usually love everything she puts on because despite getting older, this girl still has a killer body. Her style, though, is pretty simple. If she has downtime, then you will usually find her in khakis and a t-shirt, but if she’s at a red carpet event, then you will find her in something that is foxy but also elegant. We love the awesome style that she has and we never see her going down a dark and dangerous style path with her choices. Her style choices are also so simple, they are easily replicated in our own closets.

As she’s getting older, though, there have been a few times where her clothing choices made her look frumpy while other times, she dressed in outfits that made her look significantly younger. As women, we want to look younger for as long as possible. It’s nice when we can find outfits that make us feel good in our bodies as well as make us feel a little younger.

Usually, when she is on the red carpet, she wears the steamy minis that show off her incredible body or some floor-skimming gowns that are great elegant choices. We love Aniston, no matter what, even if her style choices are a little off.

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24 Jennifer Aniston Loves A Black Dress

This little black dress easily took ten years off of Aniston because it’s a fresh-looking dress and it’s also a little fun. There is no severity with this dress, it’s short and has a tight waist. It shows off her great legs and gives us that fun feeling that you can do anything in this dress. For Aniston, it’s all about balance and she's certainly been through a lot over the years. “Where would you be without friends? The people to pick you up when you need lifting? We come from homes far from perfect, so you end up almost parent and sibling to your friends — your own chosen family. There's nothing like a really loyal, dependable, good friend. Nothing.” We would have to agree and rumor has it, she likes to give her clothes to her friends.

Not The Most Flattering Florals

We are hard-pressed to find anything that Aniston looks bad in, but there are items in her closet that add a couple of years and this print dress is one of them. Sometimes, our fashion choices aren’t necessarily about what makes us look cool, but what makes us comfortable and that may have been why she chose this style. While it looks okay on her, it’s just not the type of dress that will make her look younger. This dress may not have made sense at the time, but what did make sense to Aniston was the way her career went, most specifically with Friends. It was, after all, the show that made her career. “It just felt really natural to me. A show about six people who hang out all the time. That makes perfect sense."

23 Cool Girl Through And Through

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One of Aniston’s signature styles is jeans and a t-shirt and she always looks amazing in them. We’re pretty sure it is physically impossible to wear ripped jeans and look “older.” There is just something about ripped jeans that are just eternally youthful and Aniston knows how to pull them off. We seriously love this look on her because it makes her the epitome of the “cool girl.” We often look at her t-shirts and wonder how she manages to always look amazing in them. She says there is a secret to that signature look, though. “This is my secret: The trick to t-shirts is that I usually tailor them. Which is silly, but it works. Or you just have to find the perfect one.”

22 Her Clothing Just Goes With The Flow

Another clothing choice that has Aniston looking more her age. Not that there’s anything wrong with that, but we have to say that we love it when we can admittedly say that she looks so much younger. This would be a good office look for anyone, though, especially with spring approaching. Prints are always a fresh look and this top is just as loose as the pants are and that’s a good combination. Whether you are going to dinner or to the office, this is one look that would flow well. One style choice that Aniston regretted was the hairstyle she had on Friends that became iconic. “The Rachel” made her a household name and young adults everywhere were making the style their own. She personally didn’t like how big it became and regretted the style entirely. Especially since it didn’t want to go away. “It had legs!”

21 The Minis That Shine

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Jennifer Aniston looks like one hot mama in this silver mini. The reason that Aniston has never been called a cougar is that she’s never looked old enough to be one. Whether it’s good genes or the fact that she really takes care of herself, we’re not sure, but she always looks amazing. Her hair is fun and flirty and the silver mini is honestly to die for. You would never believe for a minute that Aniston is in her 40s when she pulls up in dresses like this. From her hair, right down to her shoes, this woman looks so much younger than she really is. We feel that for the most part, Aniston is always making good decisions, especially about love. She’s always been the kind of girl that knows she will survive whether or not she has a man in her life. “A relationship isn't going to make me survive. It's the cherry on top.”

20 Not Really The Best Way To Wear Plaid

It’s really hard to say anything negative about Aniston’s style because she really does pull off most of her looks. In this case, her plaid dress isn’t taking the years off; it’s adding years to be honest. We are always so used to her coming out in something foxy or elegant that we really don’t know what to do with this plaid dress. When it comes to being a celebrity on Aniston’s level, it’s hard to do anything normal. Just look at how many photos are taken of her on a regular basis. “When somebody follows you 20 blocks to the pharmacy, where they watch you buy toilet paper, you know your life has changed.” It must be the weirdest feeling in the world to have someone follow you while you are just doing mundane tasks.

19 Aniston Slays With A Slit That Goes All The Way Up

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Jennifer Aniston always looks foxiest when she wears a floor-length dress with a slit. She rules the style and has worn it on more than one occasion and always looks like a goddess. Not to mention she easily looks ten years younger. She has the body to rock this dress and most importantly, she has the attitude. We love seeing her on the red carpet because she always dresses to impress. “It's all about being comfortable, being easy, and having you be able to wear something and not having it wear you. It's classic. Every time I've tried to be bold and crazy, I feel like a Japanese animated cartoon character.” That’s one thing about Aniston’s style is that it’s classic and never overboard.

18 It’s More Than Just A Pantsuit

We would much rather see Jennifer Aniston in a long evening gown than in a pantsuit any day. We will pass on a style like this because although it does have a revealing front, it does not show off her amazing body in any other way. The pantsuit isn’t even form-fitting and we think there could have been better fashion choices for the event than this one. We think she was playing it a little safe that year for the Critics' Choice Awards. Many people have asked Aniston over the years how she manages to stay so youthful and beautiful. "Drinking a lot of water, using really nice good products for your face. Don’t over-product, that’s the other thing. Getting proper sleep is always important. Wrinkles happen to human beings.” Now, that doesn’t seem so hard to do.

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17 She Shines In Silver

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For some reason, Aniston got a little flak for wearing this gown, but we would have to disagree. “Personally, I think the awfulness of her Saint Laurent dress is totally a two-day story, but there are other moments to discuss,” wrote Celebrity Auction. Whether it’s the design or the color, we think this is a youthful choice for Aniston. There was a lot of talk about her at the event because not only did people not like her dress (silly fools), but she came with two bodyguards and no one really knew why. Look at that dress, of course she needed two bodyguards.

16 Frumpy Fail

We are hard-pressed at times to find an outfit that Aniston doesn’t look good in, but we don’t think this one is one of her best choices. She has an amazing figure and we just feel that this one-piece failed to show it off. In fact, it was a little frumpy and definitely aged her. It appears to be made out of silk which is probably why it grabs at her body the way that it does, but it’s almost pasted on her which doesn’t show her body off in a good light. “Nobody thinks of themselves as s*xy, really. Some days you go, 'Hey, I'm not going too bad today.' But if you try and be s*xy, you'll never be s*xy.” We just love how forgiving she is of herself and her body; it would be great if more women could just cut themselves a break at times.

15 She Looks Like She's College Bound

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Leave it to Aniston to manage to make a simple pair of shorts and a tank top look amazing. It’s such a casual outfit and yet the girl makes it look flawless and amazing. This is part of her signature look, of course — Aniston loves her comfortable outfits and because her body is so toned, she always rocks a tank top. We love that Aniston is one celebrity that refuses to go under the knife. “I see them and my heart breaks. I think, 'Oh God if you only know how much older you look.' They are trying to stop the clock and all you can see is an insecure person who won’t let themselves just age. I also have a fiancé who will put a gun to my head if I touch my face in any way.” Thank you, Justin, for agreeing with us.

14 When She Walks The Streets Incognito

Well, at least she thinks so anyway until she sees herself in the media. We love Aniston’s casual and comfortable style, but this one is a little too far gone for us. She's worn this look a few times and we just don’t think it shows off her obvious natural beauty. Between the hat, the baggy sweater, and the jeans, Aniston looks more frumpy than foxy and if any look ages her more, it’s this one. When it comes to great ideas, Aniston always has a ton. “One tradition I have with my friends is that when one of us gets married, we have a ton of fragrance oils and pretty bottles at the bachelorette party. Everyone puts a drop or two in a bottle for the bride and makes a wish, and the bride wears our creation on her wedding day.”

13 Aniston Looks Like Royalty In Silver

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Silver is definitely one of this girl’s signature colors because she looks stunning in it. Anytime we see Aniston in a mini dress, we have to marvel at how amazing she looks for her age. She clearly takes very good care of herself and when it comes to exercise we have to appreciate how toned her legs are. The mini is all about showcasing the legs and she does a wonderful job of it. This is definitely one of her more youthful looks and she rocks this style every single time. Aniston says she feels at her best when she is surrounded by her friends and most of us couldn't agree more. “You know when I feel inwardly beautiful? When I am with my girlfriends and we are having a 'goddess circle.'”

12 Not Her Best Fashion Choice

Even when Jennifer was younger and rocking her fame from Friends, she didn’t always dress to impress. In this case, despite being a young girl, her outfit made her look so much older. The pants are way too loose and the top, although it is meant to show off her great figure, is awkward. We are glad to see that these days, Aniston does not make fashion choices like this one any longer. “I'm a bit of a clothes hoarder, admittedly. I try to weed out stuff. My girlfriends come over for cheese and wine and go shopping in my wardrobe. They especially love it when they get stuff with a tag still on.” Gosh, just wouldn’t that be like a dream come true. We would love to go shopping in this style queen’s closet.

11 If You Can Pull Off White...

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This is Jennifer Aniston’s classic look alright. We have never seen her look foxier or more beautiful than in this tight white dress. Her body is insane in this picture and this is easily one of the most youthful looks she could ever pull off. She’s a stunner in this picture. This is the kind of girl that you want to take shopping with you all the time. Although she looks young, she is wise beyond her years. “Most of us fall in love with someone's persona and spend the next three to five years discovering who that person really is. If you can stay connected through that process of raw vulnerability, I think you have a shot at the prize of knowing and accepting another human being for who and what they really are after years of highs and lows.”

10 Aniston Attends A PTA Meeting

Sorry Jennifer, but this is not one of your better looks. We have a feeling that Aniston is going to a parent-teacher meeting in this outfit. It’s clearly not her best look and we hate to think of her as our child’s teacher, but it’s either that or a librarian. It’s a cute dress, but we think Aniston can do so much better than this, especially since we expect so much from her. “I don't know what it means to be a s*x symbol. When I look at myself on a magazine cover, I don't see it as me, but as someone painted, fluffed, puffed, and done up.” How true is that? We all know that the girl on the magazine covers is often touched up to the extreme.

9 Aniston Walks With A Flair Of Sophistication

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We love this dress on Aniston; there is rarely a time when she is in a dress that she looks bad. This dress is less about being foxy, though, and more about sophistication and grace and as usual, she is pulling it off flawlessly. It’s classy but still has a little of the badass quality that Aniston portrays — we love the glittery elements of the dress as well. Aniston has been attacked at times in the media for her weight, but we think she’s always looked great even with a few extra pounds. “You're damned if you're too thin and you're damned if you're too heavy. According to the press, I've been both. It’s impossible to satisfy everyone and I suggest we stop trying.” Once again, she has really good advice when it comes being herself and not worrying what other people think.

8 Just When You Think She Shouldn’t Burn Her Jeans

Wow, this photo almost makes us speechless. This can’t possibly be the same Aniston. We're not sure what was going through her head when she put this outfit together, but it’s not good. The jeans are not flattering at all! The top doesn’t do anything for the entire outfit and we think this outfit needs to go, in fact, she should burn it. Lots of times, our favorite shows are changed forever when a character leaves the show. But when it came to Friend, the cast was bonded for life. “We're all with Friends until Friends dies. If one of us goes, we all go. One of us wouldn't leave. It wouldn't be the show it is without each of us.”

7 Not Everyone Can Pull Off A Leather Dress

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We love this dress on Aniston mainly because not everyone can pull off a leather dress. She looks incredible in the form-fitting dress, especially because it’s a mini. When it comes to wearing minis sometimes, it works for older women while other times it doesn’t, it all depends on the figure. But Aniston always pulls off the mini and we love her style choice. The one thing that makes her so youthful is the fact that she has no problem wearing these dresses. We love how the one shoulder shows off her toned shoulders and arms. We’re not sure if we will ever see Aniston with children, but she’s definitely someone who believes in having it all. “The women that inspire me are the ones who have careers and children; why would I want to limit myself? I've always wanted to have children and I would never give up that experience for a career. I want to have it all.”

6 What's With All The Layers?

This is another look that Aniston tried out during her younger years and it probably added ten years, so it’s a good thing that she doesn’t dress like this any longer. She is completely covered from head to toe, and even with a long dress that goes down to her ankles, she is still wearing boots. We don’t think the layered look is doing Aniston any favors. When it comes to a red-carpet event, you should always wear something that is going to make a statement and this outfit landed completely flat. We wonder how often celebs like Aniston get free clothes and random stuff from designers and companies. “I don't get sent anything strange like underwear. I get sent cookies.”

5 What's More Glamorous Than Black Sparkles?

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We love Aniston in black and if you haven’t noticed, it’s probably the choice that she goes for the most when it comes to red carpet events. One of her favorites looks is a long dress with a slit up the leg and that’s because she always looks good in these dresses. She has really nice legs and the dress showcases them off nicely. She also has a deep V neck in the front and let’s be honest Aniston has always had nice breasts so she can pull these dresses off with very little effort. Despite what the media says on occasion Aniston is one girl that always looks at the bright side of things. “You can undo a lot of things. If you're not happy, you can become happy. Happiness is a choice. That's the thing I really feel.”

4 Lady In Red 

We don’t see Aniston in ball gowns too often, but when we do, it offers a pretty big wow factor. This is quite the dress and she looks amazing in red. Judging by how amazing she looks, we’re not sure why she doesn’t wear red more often. The gown is full, the color is amazing, and Aniston has never looked happier. This is of course at the Oscars where you can’t show up just wearing any old thing. There’s no doubt about it, you can’t have the body that Aniston has without a few sacrifices, but there’s a balance she says. “I eat really well and I work out, but I also indulge when I want to. I don't starve myself in an extremist way. You're not taking away my coffee or my dairy or my glass of wine because I'd be devastated.”

3 A Casual Style That Is All Her Own

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It’s true, Aniston can still look amazing even though she is wearing the most casual attire. We love her in jeans and a tank top because it looks comfortable, but she’s still so foxy. She’s wearing a racerback tank top and by itself, it’s a pretty plain top, but all she does is add some jewelry to the look and that basic tank top is brought up to a whole new level. The tank top always shows off her amazing midriff as well. When it comes to her career choice, she’s never had any regrets. “I was told to avoid the business altogether because of the rejection. People would say to me, 'Don't you want to have a normal job and a normal family?' I guess that would be good advice for some people, but I wanted to act.'”

2 Rocking A Style That Everyone Wants

These photos are some of her most recent and it’s often shocking to realize that the girl on the right is in her late 40s. She looks better than most 20-year-olds. We love her sense of style and both of these outfits are totally her because they look comfortable and they are casual. Aniston has certainly been someone that people want to emulate. They want to copy her amazing style because it’s perfectly comfortable while being foxy all at the same time. When it comes to working, she gives us a different outlook on her life as an actor. “When you accept a role in a pilot, you automatically sign up for five years. You think it's scary to walk down the aisle? Try signing a five-year contract for a show you may not want to be part of down the road.”

1 Her Cool California Style

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When she made an appearance in this gorgeous dress, many people called it her “cool California style.” We especially love how her hair is pulled up in a high ponytail. The top of has a small peek-a-boo design to it that’s quite foxy and shows off the black waistband. Her earrings are understated which is perfect for an outfit like this. Whether Aniston is having a bad fashion day or not, she always looks amazing and it’s rare that she makes the worst-dressed list. When it comes to her youthful appearance, she attributes it to how she feels inside and maybe that’s what a lot of us need to work on. “I feel young every day.”

 

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