Top 5: The Most Fashionable Comedians

Author: Published: Mar 12th, 2012 Category: Comedians, Serial Comments: 7

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Comedy and fashion both play a big part in making Serial Optimist what it is, but both are rarely paired together. People aren’t looking at comedians for fashion inspiration, but maybe they should. Style has been in comedy since comedy has been comedy. In a variety of ways: good, bad and really bad.  Times have changed from the traditional late 80’s comedy boom and sitcom shows that came from it in the 90’s i.e.: jeans, tucked in button up, blazer, this, and…this. I’m not knocking Ricky Gervais or Louis C.K.’s choice to always wear black shirts or (far worse example) Whoopi Goldberg’s choice to always wear curtains or blankets and whatnot. That is style, and they own it. This is more about fashion, and the comedians SO think showcase it the best. Intentional or not, comedians of late have style for miles. So who are these comedy fashion icons? Read on to find out.

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Comedian (and actor, rapper, writer) Donald Glover not only dresses well, he has a real love for fashion, as you can see on his website iamdonald where he shares his favorite new lines and brands. He can rock a bow tie and suit or t-shirt and glasses and always manage to look…SWAG. See more photos on his site.

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Actor and comedian Aziz Ansari is a foodie, the guy really loves good food, his tweets will make you salivate, so it’s ironic that he pulls off the skinny tie and a always perfectly altered suit (skinny suit) so well. Even when he’s not suited up, wearing a plaid shirt with a zip-up or your basic polo, he manages to make it look cool. I mean he did just have a cameo in Kanye West and Jay-Z’s “Otis” video, which means his style is proper. (That’s what it means, right?) See more photos by Googling him.

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Natasha Leggero is glamorous. Even her name sounds glamorous. You can often see her wearing long gloves, big hats, and lots of jewelry. She knows how to accessorize in ways only she could pull off. She has great taste in the casual and simplistic as well, but if you were to put her in sweat pants and a tee, somehow how I still think she would look fierce. (Do people still say fierce?) See really wonderful photos on her site.

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Nobody, and I mean nobody, pulls of a suit better than Paul F. Tompkins. He has suit range. From three-pieces to colorful mixes to the classics, the guy is dapper. Aside from being one of the funniest comedians in the world, he seriously could be included in any “best dressed” list, (talking to you GQ). See more photos here.

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I’m making up a word to define comedian Chelsea Peretti’s style: cozy-casual-hip-chic. So four words. On stage, in the street, doing an online video, it never matters, she always looks great. She’s not making any kind of bold statement with her choices, but what she does do it make her style seem effortless, comfortable, and her. When you can do that, you make “Top 5″ lists on SO, which I’m guessing was a HUGE goal of hers. See more great cozy-casual-hip-chic photos here.

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SO Note: Photo credits: Donald Glover: Bryan Sheffield | Aziz Ansari: Uncredited from PaperMag | Natasha Leggero: Robyn Von Swank | Paul F. Tompkins: Uncredited | Chelsea Peretti: Evan Sung | All images are subject to copyright.

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7 Responses to “Top 5: The Most Fashionable Comedians”


  1. Mary
    on Aug 15th, 2011
    @ 1:45 pm

    I love how comedians can be so fashionable. Who knew that one day comedians would be fashion icons, the cool kids.


  2. Rob Delaney
    on Aug 16th, 2011
    @ 12:38 am

    Chelsea Peretti does not belong on this list. I mean, hygiene must not have been a factor. This is appalling.


  3. David Dean
    on Aug 16th, 2011
    @ 12:42 am

    What’s REALLY appalling is that you have not done a Serial Optimist interview yet Rob! We love you. Chelsea take a shower or something.


  4. Greg Johnson
    on Aug 16th, 2011
    @ 12:55 am

    I agree with Rob Delaney.


  5. Karen Dean
    on Aug 16th, 2011
    @ 1:02 am

    Love the pictures, love the comments! Fun to read.


  6. Dylan Brody
    on Mar 15th, 2012
    @ 6:17 am

    I’ve got to say, I’m deeply saddened not to have made this list.

    That is all.

    Dylan


  7. David Dean
    on Mar 15th, 2012
    @ 3:13 pm

    Dylan, you are on another level of fashionable. You are the top shelf. Everyone else is just striving to GET to where you’re at!

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