Chandler was mainly known for his wit and awkwardness, but he had a very underrated sense of style as well.
The best Chandler Bing outfits from Friends serve as a reminder of how surprisingly stylish the character was. Friends is considered to be a pinnacle of 1990s fashion. While Rachel Green is usually highlighted as the fashion trendsetter of the group with her memorable looks, the other characters definitely have some great outfits as well, especially Chandler Bing. With the tragic passing of Matthew Perry, fans have been revisiting Chandler Bing’s best moments, including some of his memorable outfits.
Chandler is generally more known for his wit and awkwardness, but he has a well-considered sense of fashion too. He often has a very 1940s-esque style, especially in the earlier seasons. While there are obviously a lot of dated ’90s looks that don’t hold up well, this vintage aesthetic allows him to stand out and look pretty timeless, and it often leads to him having a number of iconic looks that are worth revisiting.
Pink Bunny Outfit
“The One With The Halloween Party” (Season 8, Episode 6)
It’s hard to deny that this is one of Chandler Bing’s most memorable outfits even if it is not something he would want to wear on an everyday basis. However, when it comes to a Halloween costume, the giant pink bunny is not as bad as Chandler lets on. It is an instantly funny look that draws a lot of attention while also being original and stylish with its bright colors. While Chandler suggests he is embarrassed wearing it, he doesn’t start complaining until he is already dressed, hinting that he might see the stylish nature of it as well. It is certainly a better costume than Ross’ “Spudnik” choice.
Brown Vest And Pants
“The One Where Everybody Finds Out” (Season 5, Episode 14)
Although Chandler could certainly be childish, his fashion choices, especially in the earlier seasons, suggested he at least took a mature approach to his wardrobe. When it came to the outfit he chose to wear for his big “date” with Phoebe, Chandler made a wise selection of this vest and pants ensemble, giving him a sophisticated professorial look. Although Chandler’s nervous and forced flirtation with Phoebe betrayed a lot of the appeal this outfit gives off, Chandler does pull off the sharp look surprisingly well.
T-Shirt Over Long-Sleeve
“The One With The Baby on the Bus” (Season 2, Episode 6)
Some of the best Chandler Bing outfits are the ones where he seems to be taking a laidback and casual approach to his wardrobe. When he and Joey are looking after Ross’ son Ben while out in the city, Chandler rocks this classic 90s look with a large white short-sleeve shirt overlayed on top of a gray long-sleeve shirt. While it would be a bold fashion choice to pull off now, in the era of the early seasons, it was seen as a classic skater look. While Chandler doesn’t fit into that culture necessarily, it comes off as a great nonchalant look.
Beachwear
“The One With The Jellyfish” (Season 4, Episode 1)
Certain Friends destination episodes led to Chandler’s fashion looks to expand to suit the new environment. Perhaps the most memorable example of this is this stylish beach outfit. While Joey fails to embrace the beach lifestyle with a fairly simple T-shirt and shorts, Chandler stands out with a white Hawaiian shirt and blue shorts. It is a simple look that is the one Chandler Bing outfit most likely to be seen today. The Hawaiian shirt look has come back strongly in recent years with Chandler looking ahead of the curve with a fun summer look.
New Year’s Eve Outfit
“The One With The Monkey” (Season 1, Episode 10)
In season 1, Chandler was able to stand out at a holiday party. At Monica’s New Year’s Eve party, he wore a white collared shirt with a light golden tie, a crimson red sweater vest, and a forest green blazer, along with some smart pants. The look is a classic one for Chandler in the earlier seasons, as he liked to dress with a dapper vintage twist. This look adds a cozy professorial vibe, and it is perfect for the Christmas period with its festive colors. While he didn’t enjoy being at the party with Janice, the two of them together looked like a very stylish couple.
Vintage Work Wear
Multiple Episodes
Chandler always aimed for a 1940s-style vibe in the earlier seasons, and nowhere was this more obvious than with his workwear. He always wore a suit and tie, but he managed to give it a vintage spin that helped him stand out among the many other men in his office. This outfit in particular is great, with its cream shirt and brown tie and vest, as the colors and silhouette are still on-trend to this day. Even the funky pattern on the tie doesn’t ruin the impressive ensemble. Granted, dressing so professionally and sophisticatedly doesn’t stop Chandler from acting as immature as always, but he managed to pull off an adult look at least.
Plaid Blazer
“The One With Five Steaks And An Eggplant” (Season 2, Episode 5)
Oversized blazers are a popular modern fashion trend now, especially ones that are patterned, so Chandler is somewhat of a style icon for this outfit. He is wearing a brown checked blazer in what appears to be a tweed material. It’s a dark academia sort of look and something that might seem more fitting for Ross as a character, but Chandler pulls it off nicely. He also has a white t-shirt and black sweater vest underneath, further cementing it as a classic Chandler outfit. The blazer adds a nice new element, so the whole outfit ends up looking new and fresh while still staying in his comfort zone.
Pajama T-shirt
“The One With The Stoned Guy” (Season 1, Episode 15)
What is most impressive about Chandler’s style choices is how he is able to come off so well in even more leisurely ensembles. He is wearing pajamas, but the outfit still manages to stand out because of the graphic t-shirt. The 1990s is famous for its trend of vintage printed t-shirts, and Chandler’s is no exception. He pairs the look with some simple dark sweatpants to let the t-shirt stand out, and overall, it is a perfect look to lounge in. Chandler was always more comfortable hanging out in the apartment, so it is fitting that he still finds great fashion choices in this comfortable setting.
His Wedding Suit
“The One With Monica And Chandler’s Wedding” (Season 7, Episode 23)
Certainly the most important Chandler Bing outfit, this charming tuxedo look is what he wore when marrying Monica. Like many of Chandler’s best fashion choices, the tux is a fairly straightforward look only to be given a nice subtle twist that makes it stand out and become more impressive. In this case, the black tux with the black tie is accented by a nice gold vest underneath. As with most weddings, it is the bride’s dress that steals the show, but Chandler managed to get himself noticed as well when up on the altar in this ensemble.
1980’s Look
“The One With All The Thanksgivings” (Season 5, Episode 8)
Certainly the most important Chandler Bing outfit, this charming tuxedo look is what he wore when marrying Monica. Like many of Chandler’s best fashion choices, the tux is a fairly straightforward look only to be given a nice subtle twist that makes it stand out and become more impressive. In this case, the black tux with the black tie is accented by a nice gold vest underneath. As with most weddings, it is the bride’s dress that steals the show, but Chandler managed to get himself noticed as well when up on the altar in this ensemble.
1980’s Look
“The One With All The Thanksgivings” (Season 5, Episode 8)
Chandler looks great here with a green checked vest, a denim shirt with a mandarin collar, and his hair slicked back. The outfit feels very classic Chandler, but also slightly elevated, since Chandler is dressing up for Rachel’s birthday. Perhaps the green in the vest is a nod to Rachel’s last name, which is a thoughtful touch. Since Chandler is situated near Joey in most of the episode’s scenes, it is as if the costume designers wanted them to contrast one another in outfits, with Chandler in his colorful fancy look and Joey in his casual all-black outfit. It manages to get across how they are both so different, but they still enjoy each other’s company.
Miami Vice Outfit
“The One With All The Thanksgivings” (Season 5, Episode 8)
This episode had an amazing Friends flashback moment that includes a tribute to the 1980s show Miami Vice, as Chandler and Ross dress up in very similar outfits to the show’s main characters. Chandler goes for a white and faded red look, which definitely makes the statement that these outfits are supposed to make. While wearing a suit with a t-shirt isn’t something that Chandler is opposed to, the colors make it wildly different from what Chandler is usually seen wearing. However, this is set in a different time to when the show is generally set, so it’s great to see how Chandler’s style has evolved over the years.
Football Outfit
“The One With All The Football” (Season 3, Episode 9)
Another one of the classic Friends Thanksgiving episodes sees another classic Chandler look. He wears a crewneck sweatshirt over a long-sleeved shirt, along with black sweatpants and white trainers. The outfit is dark and faded in color, which is very autumnal, making it perfect for some Thanksgiving football. Chandler often wears things suitably oversized, which allows him to move in the comedically speedy way that he often does. This also makes him look younger, which works as he is the most emotionally immature of the group, which is emphasized by the backward cap. Overall, it’s a casual and comfy, yet fun and boyish look.
Crew Neck Sweater
Multiple Episodes
Sometimes less is more, and Chandler’s memorable outfits knew how to keep it simple. In multiple episodes, he wears crew neck long-sleeved sweaters or sweatshirts. He wore them in a variety of colors, but this dark-colored one helps his tanned skin stand out. He also layered a white t-shirt underneath, making the look perfect for the colder months. He usually paired the look with jeans, which are a classic wardrobe staple. Overall, the outfit is simple, but timeless and appropriate for any age. The style is still popular today, so Chandler could very much still be considered a style icon.
Oversized Shirt And Sweater Vest
“The One With The Thumb” (Season 1, Episode 3)
This look is the pinnacle of Chandler Bing’s outfits in the earlier seasons of Friends. He is wearing an oversized denim shirt, along with a black sweater vest and cream pants. The colors work well on him, and they all complement each other nicely. The look is cozy and casual, while still being very on-trend for the 1990s. The 90s-ness of the look is of course emphasized by his hairstyle, which donned the head of many a man in that decade. Viewers often wish that Chandler kept this sort of style for longer, but they can at least go back to the show’s first few seasons to get a good look at great outfits just like this one.
