It’s fascinating how my brain can easily forget important details such as birthdays, passwords, and names, while retaining an endless supply of irrelevant information. Lately, I’ve been fixated on a mental image of Jennifer Aniston and Brad Pitt shopping together at Rodeo Drive back in 1999. It’s a prime example of how my mind can store useless trivia.
Wait a minute, is this information really outdated? Well, not really when it comes to style (although that doesn’t excuse my forgetfulness in wishing you a happy birthday, Dad – sorry!). Just look at how trendy this outfit from over 20 years ago feels now. The basic tank top, the vibrant yet fitted cargo pants, the understated fanny pack, the slightly oversized but not too funny-looking sunglasses, and the highlight of the ensemble: the flatform flip flops that could easily pass for The Row’s popular Ginza sandals. It’s not difficult to envision several young Hollywood celebrities and fashion icons sporting this exact outfit today.
Take a trip down memory lane and revisit Jennifer Aniston’s fashion choices from the 90s, which are still relevant and timeless even today. Her simple and pared-back approach to style is her signature, and as a true California girl, she effortlessly combines ease and glamour. From mom jeans to slip dresses, sheer shirts to bucket hats, and chunky-soled sandals, her off-duty wardrobe is a treasure trove for fashion lovers who appreciate the vintage charm of the 90s. Don’t be surprised if you’ve seen these pieces resurface on Instagram feeds recently!
Jennifer Aniston’s fashion in the 90s was characterized by simplicity and minimalism, as seen on the red carpet. She often wore slip dresses, neutral-colored outfits, and paired them with barely-there sandals and pouch bags. Her choice of clothing in the past still feels current, as evidenced by the handkerchief top she wore to the SAG Awards in 1999. Her elbow-length gloves and strapless gown from the Emmy’s in 1995 are also timeless pieces. It’s worth noting that Jennifer has worn many black dresses over the years, proving that an LBD is a classic choice that will never go out of style.
The love for bohemian fashion is evident among California girls, and Jennifer Aniston and Courtney Cox are no exception. Although they usually stick to their laid-back style, they occasionally surprise us with fancy crochet cardigans and bras worn as outerwear, as seen in 1995. In 1999, Jennifer wore a dress to the Emmy’s with an intricately embroidered bodice that perfectly embodied the West Coast’s effortless vibe. To complete the look, she styled her famous “Rachel” haircut in tousled waves that appeared as if she had just returned from a surf session. These iconic looks are timeless and continue to inspire fashion trends to this day.
In January, Jennifer Aniston wore a vintage John Galliano for Christian Dior white bias-cut dress to the SAG Awards. The design, from 1999, was picked up from luxury Beverly Hills vintage boutique LILY et Cie. According to owner Rita Watnick, Aniston and her team have sought out special pieces from the boutique in the past. It was a stylish move that seemed meta, as Aniston looked modern and chic while wearing something that could have been from her previous red carpet appearances. Clearly, Aniston has always had a good sense of what works for her.
In an article I wrote for Grazia during Jennifer Aniston’s 50th birthday, I shared my personal encounter with her at The Sunset Tower hotel bar in LA. I used to believe that the expression “lighting up the room” was overused, but Aniston truly possesses a radiant and captivating charisma that immediately draws you in. Although I can’t recall what she was wearing that night, it’s actually a compliment to her incredible sense of style and fashion. Aniston always manages to wear the clothes so effortlessly, making her a true fashion icon.
