Friends: Chandler’s 10 Best Outfits

Friends is considered the pinnacle of 1990s fashion. While the title “fashionista” often goes to Rachel Green, the other characters also have great outfits. This includes Chandler Bing.

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Chandler is generally best known for his wit and goofiness, but he also has a keen sense of fashion. It often has a very 1940s style, especially in the early seasons. This vintage aesthetic helps him stand out and look quite timeless, and it often leads to him having a number of iconic looks, which are worth discussing.


New Year’s outfit – “The one with the monkey”

friends chandler janice

In season 1, Chandler was able to cause a stir at a holiday party. At Monica’s New Year’s Eve party, he wore a white collared shirt with a light gold tie, a crimson red sweater vest and a forest green blazer, along with smart pants.

The look is a classic for Chandler in previous seasons, as he liked to dress with a dapper vintage touch. This look adds a warm professorial vibe and is perfect for Christmas time with its festive colors. Although he didn’t enjoy being at the party with Janice, the two together look like a very stylish couple.

Vintage Workwear – Multiple Episodes

Chandler Bing sitting on a couch in Central Perk in Friends

Chandler has always aimed for a 1940s-style vibe in previous seasons, and nowhere was that more apparent than with his workwear. He always wore a suit and tie, but he managed to give him a vintage touch that helped him stand out among the many other men in his office.

This outfit in particular looks stunning, with its cream shirt and brown tie and waistcoat, as the colors and silhouette are still in style to this day. Even the funky pattern on the tie is something viewers can find at Urban Outfitters. Granted, the fact that he dresses so professionally and sophisticatedly doesn’t stop Chandler from often coming up with quotes that make him the worst, according to some viewers.

Plaid Blazer – “The one with five steaks and an eggplant”

Oversized blazers are hot right now, especially patterned ones, so Chandler is something of a style icon for this outfit. He wears a brown plaid blazer in what appears to be a tweed fabric. It’s kind of a dark academic look, and something viewers might expect Ross to wear, but Chandler can still pull off.

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Viewers can also see that he’s wearing a white t-shirt and a black sweater underneath, which is obviously a classic Chandler outfit. The blazer adds the right amount of jazz so that the whole outfit ends up looking new and fresh while still staying in its comfort zone.

Pajama T-Shirt – “The One with the Stoned Guy”

Friends, Mr. Costellic offers Chandler more money and he gives in

This look occurs as he teases Joey and Ross about their dirty talk and also accepts his own work, two situations that result in some of Chandler’s most memorable quotes. He’s wearing pajamas, but the outfit still manages to stand out for the graphic tee. The 1990s are famous for their funky vintage printed tees, and Chandler is no exception.

He pairs the look with simple dark sweatpants to make the t-shirt stand out, and overall, it’s a perfect look for chilling out. Also, while it’s not exactly part of the outfit, his hair looks great and many viewers wished he kept that hairstyle after season 1.

1980s look – “The one with all the Thanksgiving”

Matthew Perry, Jennifer Aniston, David Schwimmer and Courteney Cox as Chandler, Rachel, Ross and Monica in Friends

Chandler definitely figured out what decade he was in with this outfit. Granted, this episode has Chandler doing a lot of things wrong that some viewers choose to ignore, like belittling Monica about her weight. His crazy outfit almost seems to hint at how crazy he acts. The oversized blazer and pants are one thing, but it’s his Flock of Seagulls haircut that really takes over.

Plus, even though people like to think of the 1980s as a brightly colored era, brown was actually an immensely popular color, so Chandler’s outfit seems quite fashionable for the era. Brown is also a trendy color today, if any viewers want to recreate that look.

Denim shirt and green waistcoat – “The one Rachel discovers”

Friends - Chandler and Joey

Chandler looks great here in a green plaid cardigan, a mandarin collar denim shirt and his slicked back hair. The outfit looks like a very classic Chandler, but also slightly elevated, since Chandler is dressing up for Rachel’s birthday. Perhaps the green of the vest is a nod to Rachel’s last name, which is a thoughtful touch.

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Since Chandler is located near Joey in most scenes in the episode, it’s as if the costume designers wanted them to contrast each other in outfits, with Chandler in his colorful fancy look and Joey in his fully casual outfit. black. He 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 Thanksgiving”

This episode had an amazing Friends flashback moment that viewers may have forgotten. This includes a tribute to the 1980s show miami vice, as Chandler and Ross dress in outfits very similar to the show’s main characters. Chandler goes for a faded white and red look, which definitely drives home the statement these outfits are meant to make.

Although Chandler doesn’t object to wearing a costume with a t-shirt, the colors make it look very different from what fans usually expect Chandler to wear. But it’s set in a different time than the show usually takes place, so it’s great to see how Chandler’s style has evolved over the years.

According to Ranker, it is one of Friends‘ best episodes, and he definitely has one of Chandler’s best outfits. He wears a crew-neck sweatshirt over a long-sleeved shirt, along with black sweatpants and white sneakers. The outfit is dark and a faded color which is very autumnal, making it perfect for a Thanksgiving football game.

Chandler often wears oversized clothing, which allows him to move around in the comically fast manner he often does. It also makes him look younger, which works because he’s probably the most emotionally immature of the bunch, which is emphasized by the backwards cap. Overall, it’s a casual and comfortable look, yet fun and boyish.

Crew Neck Sweater – Multiple Episodes

Joey and Chandler at Monica's apartment in Friends

Sometimes less is more, and Chandler has always kept it simple. In several episodes, he wore crewneck, long-sleeved sweaters or sweatshirts. He wore them in a variety of colors, but this dark color helps his tanned skin stand out. He also layered a white t-shirt underneath, making the look perfect for the colder months.

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He usually paired the look with jeans, which are a classic wardrobe staple. Overall, the outfit is simple, yet timeless and suitable for any age. The style is still popular today, so Chandler could still be considered a style icon.

Oversized Shirt and Sweater Vest – “The One with the Thumb”

This outfit is the pinnacle of Chandler Bing’s style in previous seasons. He wears an oversized denim shirt, along with a black sweater vest and cream pants. The colors suit her well and they complement each other well. The look is comfortable and casual, yet still very trendy for the 1990s. The 90s edge of the look is of course underscored by his hairstyle, which styled the heads of many men during that decade.

Viewers often wish Chandler kept that kind of style for longer, but they can at least go back to the early seasons of the show to get a good look at great outfits like this.

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