One of the highlights of the mega-hit sitcom Friends is Rachel’s iconic fashion sense and flawless taste in clothing. From popularizing the Rachel hairstyle to showing fans how to carve a niche in the fashion industry, she did it all.
In the show’s finale, Rachel was offered a well-paid job in Paris with Louis Vuitton but she chose to stay back in New York with Ross. She chose love above all and, in the process, dated extremely fashion-forward men. Here’s recalling Rachel’s dating history with a view to honor the best-dressed men she dated throughout the course of Friends.
Chip Matthews was someone Monica and Rachel went to high school with and frankly, he was pretty much unimportant. He was on-again, off-again with Rachel during their time at Lincoln High. Their romance came to an end after he abandoned her at the prom for Amy Welsh.
The one and only good thing about Chip is that he wore nice jackets. In high school, he was known for his letterman jacket, and on his date with Monica in “The One With The Cat,” he sported a classic blue oversized jacket. Much to Rachel’s delight, Monica dumped Chip at the end of their date and that was it for him on the show.
Shortly after Rachel’s ugly breakup with Ross, she dated a college student to get back at him for dating Amanda. The guy was named Josh and he ended up stealing money from her and jewelry from her roommate, Monica.
There was nothing commendable about Josh except his cool casual style. Since he played soccer, he was dressed in comfortable athleisure pieces. Once seen in activewear, and the second time in a chic blue sweatshirt, Josh’s sport-specific clothing complemented his athletic body well. The current athleisure trend shows no signs of slowing down, and therefore Josh is one of Rachel’s best-dressed exes even today.
Rachel’s first and only date with Joey’s Days of Our Lives co-actor, Kash didn’t go so well after she told him she was pregnant. All things aside, he did dress up well – the first time on the set of DOOL and another time when he arrived at Rachel’s to pick her up for the date.
Kash looked elegant in his striped V-neck sweater and pants on the date night. The outfit was a perfect blend of sophisticated yet playful, and a good choice to make the first impression on a woman who worked in fashion.
Once Danny shaved off his beard, and cut his hair, he was no longer the “hairy beast-man” as Rachel had described him before. He turned out to be a good-looking person with great style. Danny called out Rachel for obsessing over appearances and she defended her snap judgment about him.
After a while of flirting back and forth in the hallway, Monica set them up and they seemed happy together. Danny mostly wore black and grey on the show and topped off the outfits with a leather jacket. His abnormally intimate relationship with his sister became a solid reason for Rachel to dump him and to never look back again.
Rachel and Joey’s romance flopped for various reasons but their friendship did wonders for his wardrobe. He wore what he liked, and, more often than not, it suited him well. Of course, it always helped to have Rachel around as she worked for one of the biggest fashion houses in the world.
Rachel once dressed Joey in a dark olive shirt and tie at Bloomingdale’s for his audition. She also sent him a bag of 10 free Ralph Lauren shirts. All in all, Joey looked suave in leather jackets, straight-legged jeans, and incredibly nice GAP shirts.
Everything seemed okay between Rachel and her Italian boyfriend Paolo until she learned he’d made a move on one of her closest friends, Phoebe. After Rachel was done throwing Paolo’s clothes off the balcony, Ross spoke for everyone when he shut the door in his face.
Paolo wasn’t a great guy or even a decent guy for that matter, but he sure was a great dresser. A fit bloke in tight clothes, he dressed well for his body type. Fans remember him for his leather jacket, voluminous curly mane, and for gifting Rachel a cute pair of black Italian shoes.
Rachel was Joshua’s personal shopper at Bloomingdale’s and by the end of the week, they were completely was smitten with each other. He preferred a relaxed style of office wear and yet, he bought 6 suits from Rachel just so he could see her. As for her, she organized a fake goodbye party to spend time with him.
Joshua looked quite good in both formal and casual wear. He mostly wore blazers, and white t-shirts underneath solid-color sweaters, and Rachel was won over.
In season 3, Rachel was able to break into the fashion industry thanks to Mark who got her an interview at Bloomingdale’s. At first, the two were friendly co-workers, but after she broke up with Ross, he finally gathered the courage to ask her out.
Being as Mark worked in the fashion industry, he was a well-dressed man. He wore elegant suits to work and his casual outfits were deeply influenced by his unique personal style.
Gavin filled in for Rachel for while she was on her maternity leave in season 9. After she rejoined, she felt insecure about his presence in her office and wanted him out of there. Once Gavin and Rachel were done being frenemies, he went ahead and confessed his feelings to her.
Gavin was usually dressed in smart suits and elegant ties for work. His casual outfits were equally fashionable. His off-duty look on Rachel’s birthday was nearly perfect. Gavin was easily one of the nicest guys Rachel dated on Friends.
The first time Tag walked into Rachel’s office, she mistook him for a male model and redirected him down the hall. Yes, he was that well-dressed and charming. They had a fun-filled relationship which sadly came to an end on Rachel’s 30th birthday because she felt she needed to be with someone more mature.
Tag dressed well for a job that required him to look professional and stylish. He was equally debonair outside of work. He and Rachel looked splendid every time they stood side by side.
NEXT: Friends: 5 Reasons Rachel Should Have Been With Tag (& 5 Why Ross Was The Right Choice)
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