Friends: Chandler’s 10 Best Outfits

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

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. This vintage aesthetic allows him to stand out and look pretty timeless, and it often leads to him having a number of iconic looks, which are worth discussing.

New Year’s Eve Outfit – “The One With The Monkey”

In season 1, Chandler knew how to make a big splash at a holiday party. To 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 look 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 apparent 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 amongst 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 is something that viewers can find at Urban Outfitters. Granted, him dressing so professionally and sophisticated 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 super on-trend right 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 viewers might expect Ross to wear, but Chandler can still definitely pull it off.

Viewers can also see that he has a white t-shirt and black sweater vest 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 his comfort zone.

Pajama T-shirt – “The One With The Stoned Guy”

This look happens while he is teasing Joey and Ross about their dirty talk and also accepting his own job back, two situations that result in some of Chandler’s most memorable quotes. He is wearing pajamas, but the outfit still manages to stand out for the graphic t-shirt. The 1990s is renowned for its funky 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. Furthermore, while it’s not exactly part of the outfit, his hair looks great, and many viewers wished he kept this hairstyle past season 1.

1980’s Look – “The One With All The Thanksgivings”

Chandler definitely got across what decade he was in with this outfit. Granted, this episode has Chandler doing many things wrong that some viewers choose to ignore, such as belittling Monica over her weight. His crazy outfit almost seems to be hinting at how crazy he acts. The oversized blazer and pants are one thing, but it’s his Flock of Seagulls haircut that really takes the look over the top.

Also, as much as people like to see the 1980s as a brightly colored time, brown was actually an immensely popular color, so Chandler’s outfit seems right on trend for the time period. Brown is also a trendy color today, if any viewers wish to recreate this look.

Denim Shirt And Green Vest – “The One Where Rachel Finds Out”

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”

This episode had an amazing Friends flashback moment that viewers may have forgotten about. This 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 gets across 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 fans usually expect Chandler to wear. But 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.

According to Ranker, this is one of Friends‘ best episodes, and it certainly has one of Chandler’s best outfits. 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 likely the most emotionally immature of the group, which is emphasized by the backwards cap. Overall, it’s a casual and comfy, yet fun and boyish look.

Crew Neck Sweater – Multiple Episodes

Sometimes less is more, and Chandler always knew how to keep it simple. In multiple episodes, he wore crew neck long sleeve sweaters or sweatshirts. He wore them in a variety of colours, but this dark coloured one helps his tanned skin stand out. He has 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”

This outfit is the pinnacle of Chandler Bing’s style in the earlier seasons. He is wearing an oversized denim shirt, along with a black sweater vest and cream pants. The colours work well on him, and they all compliment 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.

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