Aniston catapulted to stardom after landing her inaugural television role on the hit show “Friends.”

At the Primetime Emmy Awards in September 1995, Jennifer Aniston was spotted on the red carpet alongside her “Friends” colleague, Matthew Perry. While her fashion choices were typically laid-back, she often opted for a simple yet stylish combination of jeans and a T-shirt. Moreover, she effortlessly rocked the iconic “The Rachel” hairstyle, which quickly gained popularity during the 90s.

Fast forward to 1997, and Aniston once again graced the red carpet, this time donning another timeless and elegant Little Black Dress (LBD). Her fashion choices continued to captivate audiences as she effortlessly showcased her effortless style and fashion sense.

Aniston effortlessly sports a timeless updo, reminiscent of the iconic hairstyle her popular character Rachel Green would often flaunt in the hit show “Friends”. And she’s not alone in her fashion choices, as other members of the beloved cast have also donned elegant black dresses.

Jennifer Aniston and Lisa Kudrow made a joint appearance at the “Friends Helping Friends” party back in November 1997. On this occasion, Aniston chose to complement her knee-length strapless gown with a hairstyle that shimmered under the lights. It seems that Aniston ventured to try out different looks during her relationship with Brad Pitt, showcasing her willingness to explore and embrace new styles.

Brad Pitt and Jennifer Aniston make a glamorous entrance at the 51st Annual Primetime Emmy Awards. The actress surprises everyone by opting for a sequin-embellished dress, showcasing a completely different style from her usual fashion choices. In addition to that, she also flaunts a new hairstyle, adding an extra element of surprise. Aniston enhances the elegance of her little black dress (LBD) by accessorizing it with a modest necklace, effortlessly elevating the overall look.

At The 10th Annual Fire Ice Ball, Courteney Cox, Jennifer Aniston, Lisa Kudrow, and Renee Zellweger were seen posing together, radiating elegance and charm. The event showcased Aniston’s new trendy and chic shorter haircut, proving her versatility and willingness to change up her style. Surprisingly, in 2001, rather than her usual black dress, Aniston opted for a different, yet equally stunning outfit that she effortlessly flaunted on the red carpet, solidifying her status as a fashion risk-taker.

Matching outfits were a common sight for Aniston and Pitt back in the day, as they strolled down red carpets together. One particular example from the early 2000s stands out, where Aniston flaunts her midriff in a stylish ensemble, sans the crop top.

Brad Pitt and Jennifer Aniston caught everyone’s attention as they graced the red carpet for the premiere of “Rock Star.” In a striking ensemble, Aniston’s skirt hung gracefully, though it was not accompanied by a dress. This captivating look provided a glimpse into Aniston’s evolving and renowned edgy fashion sensibility.

It was quite surprising to see Jennifer Aniston’s bold fashion choice during NBC’s 75th Anniversary Special in 2002. However, she effortlessly pulled it off and looked stunning. Another instance where Aniston proved her style prowess was when she won an Emmy for her role in “Friends.” She donned a beautifully adorned blush pink gown that was truly ahead of its time.

With a joyous grin, Jennifer Aniston lovingly embraces her well-deserved Emmy award for her impeccable performance as the Outstanding Lead Actress in a Comedy Series. Captured by the lens of Robert Mora/Getty Images, her radiant personality shines brightly as she holds the renowned accolade in her hands.

Interestingly, while fashion trends may come and go, there is something timeless about Aniston’s choker necklace. It effortlessly exudes a trendy aura, captivating hearts both in the past, back in 2002, and even in the present day.

When it comes to fashion, Aniston has an undeniable knack for effortlessly styling a pair of black dress pants. With her innate sense of elegance, she knows precisely how to showcase their versatility and sophistication, elevating any ensemble she adorns them with.

Jennifer Aniston proudly clutches her well-deserved People’s Choice Award for her outstanding portrayal as a beloved female TV performer. A snapshot captured in 2003 reveals her flaunting a timeless all-black ensemble, accentuated by a fashionable thick choker that adds a modern twist to her overall look. Stepping onto the red carpet at the Golden Globes in 2004, Aniston radiated elegance in a stunning floor-length black gown boasting a daring deep V-neckline and a captivating statement buckle intricately adorning her attire.

Jennifer Aniston made an appearance at the 61st Annual Golden Globe Awards, flaunting her bold fashion choices during the mid-2000s. Embracing the trends of that era, Aniston confidently donned a mesmerizing sequin dress with a plunging neckline.