I thought it’d be a fun segment to do fashion breakdown for both Angelina and Jen through the years and how their style has developed over the course of their history as well as relationships.  The two very interesting and dynamic fashion icons have very distinctive styles true to their character. I always say, ‘style should reflect your inner voice and persona’ so these two women are fabulous examples of that. Although they don’t happen to share much in common other than their taste in men, they always stand out in a crowd no matter what. I know you wanna know what’s up with that, so lets extract their secret.

Angelina Jolie – rocking the Grunge and the glam

Angelina is the kind of girl who grew up having a face you knew, the type you could remember forever. Her beauty by no means is conventional, but convention is boring and Angelina is proving fact to that. She doesn’t have the most symmetrical face nor the cute femininity a lot of women are expected to have to be favored. Angelina is a big ‘ Fuck you’ to those people. She has an edge about her and because she’s aware, she makes it work through her style and getup.

The 90’s

Angelina has a kind of Rebellious rock chick vibe about her. By the ’90s and early 2000s, she started to embrace her inner gothic rocker side, wearing graphic tees and black clothing that only seemed to accentuate her pale complexion. During her Relationship with Billy Bob Thornton, she was truly able to embrace her Dark side. Short black hair and a lot of leather. It worked so well for her, one of my favorite looks actually. The Badass vibe did line up with her nonchalant mysterious persona.

In 1997, Angelina had emerged in the public eye as an actor in her own right. And one with a darker side than Hollywood was used to, as evidenced by this shaved ‘do. Her style was actually similar to one of her bigger characters: Lara Croft, which exclusively wore rugged boots and tight-fitting black clothes.

Angelina grows up and steps out Goth. In 1997 the up-and-coming actress hit the red carpet of her film, “Playing God”. Her shaved do was a vital mode of transition to a new her.

By this time, we thought we had her style figured out. But, surprise, she makes another unexpected change.  She turns up with a blonde style that was much more Marilyn Monroe than downtown punk. We see Angelina in Angelina Jolie in’ Gone in 60 Seconds’ taking big bold steps to experiment with her look. Although this lighter hair on her is not my favorite, her confidence makes her look godly.

Angelina’s has had a lifelong love for menswear and occasionally shows in her Androgenous style. Maybe it reflects her inner masculinity?. There several ways for women to express who she is, Angelina is ballsy enough to do it through fashion.

Angelina Jolie

Angelina finally enters the Glam scene, dressed in gorgeous gowns with a little bit of shimmer. She begins to embrace this mature womanly version of her still dynamic and powerful. It’s important to note that Angelina transforms into a new style that reflects her new persona instead of hiding it. This is a fabulous evolution that has taken place.

After Angelina picked her second Golden Globe for her role as the damaged supermodel Gia in 1999, she celebrated her win by diving into the Beverly Hilton Hotel pool wearing her glamorous Randolph Duke gown! ‘Gia’ definitely did have some type of an influence on her later outfits- really taking glam to the next level.

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I think Angie’s style truly transformed after she met Brad. All the way from Glam to total Hollywood chic. From a little glitter to lots and lots of it. I think it’s true when they say a relationship can change you and in this case it’s an amazing change into something that truly accentuates her beauty. Brad did her good I guess?


Angelina finally steps into a more couture look, with long gowns and bodycon dresses. I think she’s finally found a balance between her inner rebel with a more feminine touch. It looks complete , hopefully it’s not because I’m excited to see what Angie’s got in store for us next!


Jennifer Aniston-  keeping it boho easy 

If you’re talking about truly effortless fashion, Jen is your girl! Every look feels absolutely natural and unforced as a result of her effortless Californian style. Unlike Angelina she is a true conventional beauty, the simple girl next door. Her California girl look is what defines her style, and not to forget her character ‘Rachel Green’ that set the fashion bars extremely high with yet also a simple girl next door look. Jen proves you can stand out without dressing to stand out, just be you!

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90’s- 2000’s

Her look is a perfect balance of simplicity and femininity. Jen loves her shirts and trousers however occasionally you’ll catch her rocking beautiful floral and Sundresses. Her casual white tees and tanks are really iconic to her beachy Cali look. Like a true child of the 90’s, Jennifer Aniston played into the big hair and oversized tees of the time, sporting a boxy blouse tucked into jeans with a chunky looped belt to pull it all together. 


She’s gone through phases of crochet tops, leather trench coats to bejeweled evening gowns. Although still simple, I love that Jen knows what works for her and what doesn’t- dressing safe is also a way of acknowledging what looks great on you and really brings out that stunning California Tan. Jen is always up to date with the trends yet maintaining her own appeal.

Looking flawless for any decade in a satin midi dress, strappy heels and hair styled in beachy waves, Jennifer Aniston is giving us all the feels of current trends

Her looks with Brad were also consistent to her persona, and her laid back approach.we could wonder if there was really much growth at all? Maybe not. She seems to enjoy her tank tops and occasional florals. Jen may not be as experimental Angie but her style manages to really do justice to her look and complexion therefore I’m still on board with her repetitive looks. Somehow she convinced me every time.

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Her go-to looks included a jeans-and-T-shirt ensemble, and a classic Little Black Dress. “The Rachel” hairstyle also became a huge ’90s trend. We Can NOT forget the Rachel look, probably what really defines her after all. 

Jen was seen in cute mini’s, tube tops and thigh high boots and occasional florals that reflected her true style. Jennifer Aniston as Rachel Green was an influencer before influencer was even a thing so kudos to her!

Lastly, a not so surprising common ground…Blazers and Suits! It’s quite clear that both Angelina and Jennifer love their suits, it really shows them as strong independent women who turned their lives around, made big successes happen and really don’t need a man to influence them in any way or form.

One may show confidence in simplicity while another may show it in bold dressy looks. It’s okay to wear whatever you want as long as you feel like it fits ‘you’ as a person. Both these women are total risk takers and unafraid to put themselves out there, they literally wear exactly what they want and that is simply their secret, it’s confidence. Confidence can turn rags to riches. So own yourself babe, don’t overthink it.