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23 Of The Toughest “Would You Rather” Style Questions Ever

Is it better to be underdressed or overdressed?

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  1. Would you rather...

    Burn your favorite leather jacket rescuing a puppy from a fire?
    Via nastygal.com
    Burn your favorite leather jacket rescuing a puppy from a fire?
    Or burn your favorite jean jacket rescuing a puppy from a fire?
    Via urbanoutfitters.com
    Or burn your favorite jean jacket rescuing a puppy from a fire?

23 Of The Toughest “Would You Rather” Style Questions Ever

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Would you rather...
  1. Burn your favorite leather jacket rescuing a puppy from a fire?
     
    vote votes
    Burn your favorite leather jacket rescuing a puppy from a fire?
  2. Or burn your favorite jean jacket rescuing a puppy from a fire?
     
    vote votes
    Or burn your favorite jean jacket rescuing a puppy from a fire?
  1. Would you rather...

    Wear a funny/scary Halloween costume?
    Via Paramount Pictures
    Wear a funny/scary Halloween costume?
    Via Paramount Pictures
    Or wear a sexy Halloween costume?
    Via Paramount Pictures
    Or wear a sexy Halloween costume?
    Via Paramount Pictures

23 Of The Toughest “Would You Rather” Style Questions Ever

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Would you rather...
  1. Wear a funny/scary Halloween costume?
     
    vote votes
    Wear a funny/scary Halloween costume?
  2. Or wear a sexy Halloween costume?
     
    vote votes
    Or wear a sexy Halloween costume?
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  1. Would you rather...

    Wear heels that are kinda ugly and old but super comfortable?
    Via us.asos.com
    Wear heels that are kinda ugly and old but super comfortable?
    Or wear gorgeous heels that everyone loves but torture your feet and give you blisters?
    Via us.asos.com
    Or wear gorgeous heels that everyone loves but torture your feet and give you blisters?

23 Of The Toughest “Would You Rather” Style Questions Ever

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Would you rather...
  1. Wear heels that are kinda ugly and old but super comfortable?
     
    vote votes
    Wear heels that are kinda ugly and old but super comfortable?
  2. Or wear gorgeous heels that everyone loves but torture your feet and give you blisters?
     
    vote votes
    Or wear gorgeous heels that everyone loves but torture your feet and give you blisters?
  1. Would you rather...

    Get matching shirts with your pet?
    Via Imgur
    Get matching shirts with your pet?
    Via Imgur
    Or get matching shirts with your significant other?
    Via Twitter: @coliegestudent
    Or get matching shirts with your significant other?

23 Of The Toughest “Would You Rather” Style Questions Ever

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Would you rather...
  1. Get matching shirts with your pet?
     
    vote votes
    Get matching shirts with your pet?
  2. Or get matching shirts with your significant other?
     
    vote votes
    Or get matching shirts with your significant other?
  1. Would you rather...

    Buy something cute and cheap from a big retailer even though you know they're ripping someone off?
    Via Instagram: @tuesdaybassen
    Buy something cute and cheap from a big retailer even though you know they're ripping someone off?
    Or buy the original design from the original designer even though it might be a little pricier?
    Via instagram.com
    Or buy the original design from the original designer even though it might be a little pricier?

23 Of The Toughest “Would You Rather” Style Questions Ever

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Would you rather...
  1. Buy something cute and cheap from a big retailer even though you know they're ripping someone off?
     
    vote votes
    Buy something cute and cheap from a big retailer even though you know they're ripping someone off?
  2. Or buy the original design from the original designer even though it might be a little pricier?
     
    vote votes
    Or buy the original design from the original designer even though it might be a little pricier?
  1. Would you rather...

    Wear something covered in cat hair all day?
    Via how-to-get-rid.net
    Wear something covered in cat hair all day?
    Or wear a stained shirt all day?
    Via ThinkStock
    Or wear a stained shirt all day?
    Via ThinkStock

23 Of The Toughest “Would You Rather” Style Questions Ever

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Would you rather...
  1. Wear something covered in cat hair all day?
     
    vote votes
    Wear something covered in cat hair all day?
  2. Or wear a stained shirt all day?
     
    vote votes
    Or wear a stained shirt all day?
  1. Would you rather...

    Be deathly allergic to leather?
    Via ThinkStock
    Be deathly allergic to leather?
    Via ThinkStock
    Or be deathly allergic to lace?
    Via ThinkStock
    Or be deathly allergic to lace?
    Via ThinkStock

23 Of The Toughest “Would You Rather” Style Questions Ever

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Would you rather...
  1. Be deathly allergic to leather?
     
    vote votes
    Be deathly allergic to leather?
  2. Or be deathly allergic to lace?
     
    vote votes
    Or be deathly allergic to lace?
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  1. Would you rather...

    Wear a velvet tracksuit with bling every day for a year?
    Via juicycouture.com
    Wear a velvet tracksuit with bling every day for a year?
    Or wear an Ed Hardy shirt every day for a year?
    Via veqas.us
    Or wear an Ed Hardy shirt every day for a year?
    Via veqas.us

23 Of The Toughest “Would You Rather” Style Questions Ever

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Would you rather...
  1. Wear a velvet tracksuit with bling every day for a year?
     
    vote votes
    Wear a velvet tracksuit with bling every day for a year?
  2. Or wear an Ed Hardy shirt every day for a year?
     
    vote votes
    Or wear an Ed Hardy shirt every day for a year?
  1. Would you rather...

    Get terrible tan lines because of a cute bikini top?
    Via missguidedus.com
    Get terrible tan lines because of a cute bikini top?
    Wear a long-sleeve bathing suit top in 100-degree weather?
    Via lollicouture.com
    Wear a long-sleeve bathing suit top in 100-degree weather?

23 Of The Toughest “Would You Rather” Style Questions Ever

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Would you rather...
  1. Get terrible tan lines because of a cute bikini top?
     
    vote votes
    Get terrible tan lines because of a cute bikini top?
  2. Wear a long-sleeve bathing suit top in 100-degree weather?
     
    vote votes
    Wear a long-sleeve bathing suit top in 100-degree weather?
  1. Would you rather...

    Dress like an '80s girl forever?
    Via ThinkStock
    Dress like an '80s girl forever?
    Via ThinkStock
    Or dress like you're 80 forever?
    Via ThinkStock
    Or dress like you're 80 forever?
    Via ThinkStock

23 Of The Toughest “Would You Rather” Style Questions Ever

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Would you rather...
  1. Dress like an '80s girl forever?
     
    vote votes
    Dress like an '80s girl forever?
  2. Or dress like you're 80 forever?
     
    vote votes
    Or dress like you're 80 forever?
  1. Would you rather be...

    Underdressed for an event?
    Via Kevin Winter / Getty Images
    Underdressed for an event?
    Via Kevin Winter / Getty Images
    Or overdressed for an event?
    Via MGM
    Or overdressed for an event?
    Via MGM

23 Of The Toughest “Would You Rather” Style Questions Ever

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Would you rather be...
  1. Underdressed for an event?
     
    vote votes
    Underdressed for an event?
  2. Or overdressed for an event?
     
    vote votes
    Or overdressed for an event?
  1. Would you rather...

    Only be allowed to wear caps for the rest of your life?
    Via unifclothing.com
    Only be allowed to wear caps for the rest of your life?
    Only be allowed to wear beanies for the rest of your life?
    Via us.asos.com
    Only be allowed to wear beanies for the rest of your life?

23 Of The Toughest “Would You Rather” Style Questions Ever

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Would you rather...
  1. Only be allowed to wear caps for the rest of your life?
     
    vote votes
    Only be allowed to wear caps for the rest of your life?
  2. Only be allowed to wear beanies for the rest of your life?
     
    vote votes
    Only be allowed to wear beanies for the rest of your life?
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  1. Would you rather...

    Wear cargo pants forever?
    Via ThinkStock
    Wear cargo pants forever?
    Via ThinkStock
    Or wear your collar popped forever?
    Via Twitter: @AspiringRegular
    Or wear your collar popped forever?

23 Of The Toughest “Would You Rather” Style Questions Ever

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Would you rather...
  1. Wear cargo pants forever?
     
    vote votes
    Wear cargo pants forever?
  2. Or wear your collar popped forever?
     
    vote votes
    Or wear your collar popped forever?
  1. Would you rather...

    Run into your sworn enemy wearing an outfit you hate?
    Via Christopher Polk / Staff
    Run into your sworn enemy wearing an outfit you hate?
    Via Christopher Polk / Staff
    Or run into your ex looking like shit?
    Via Jag Gundu / Stringer
    Or run into your ex looking like shit?
    Via Jag Gundu / Stringer

23 Of The Toughest “Would You Rather” Style Questions Ever

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Would you rather...
  1. Run into your sworn enemy wearing an outfit you hate?
     
    vote votes
    Run into your sworn enemy wearing an outfit you hate?
  2. Or run into your ex looking like shit?
     
    vote votes
    Or run into your ex looking like shit?
  1. Would you rather...

    Have an unlimited supply of the perfect white t-shirts?
    Via ThinkStock
    Have an unlimited supply of the perfect white t-shirts?
    Via ThinkStock
    Or have an unlimited supply of the perfect little black dresses?
    Via ThinkStock
    Or have an unlimited supply of the perfect little black dresses?
    Via ThinkStock

23 Of The Toughest “Would You Rather” Style Questions Ever

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Would you rather...
  1. Have an unlimited supply of the perfect white t-shirts?
     
    vote votes
    Have an unlimited supply of the perfect white t-shirts?
  2. Or have an unlimited supply of the perfect little black dresses?
     
    vote votes
    Or have an unlimited supply of the perfect little black dresses?
  1. Would you rather...

    Wear non-prescription glasses as a fashion statement?
    Via ThinkStock
    Wear non-prescription glasses as a fashion statement?
    Via ThinkStock
    Or wear sunglasses at night as a fashion statement?
    Via ThinkStock
    Or wear sunglasses at night as a fashion statement?
    Via ThinkStock

23 Of The Toughest “Would You Rather” Style Questions Ever

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Would you rather...
  1. Wear non-prescription glasses as a fashion statement?
     
    vote votes
    Wear non-prescription glasses as a fashion statement?
  2. Or wear sunglasses at night as a fashion statement?
     
    vote votes
    Or wear sunglasses at night as a fashion statement?
  1. Would you rather...

    Only wear outfits straight out of the 1920s?
    Via Topical Press Agency / Stringer
    Only wear outfits straight out of the 1920s?
    Via Topical Press Agency / Stringer
    Only wear outfits straight out of the 1970s?
    Via Keystone / Stringer
    Only wear outfits straight out of the 1970s?
    Via Keystone / Stringer

23 Of The Toughest “Would You Rather” Style Questions Ever

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Would you rather...
  1. Only wear outfits straight out of the 1920s?
     
    vote votes
    Only wear outfits straight out of the 1920s?
  2. Only wear outfits straight out of the 1970s?
     
    vote votes
    Only wear outfits straight out of the 1970s?
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  1. Would you rather...

    Have a closet filled ONLY with prints and bright colors?
    Via ThinkStock
    Have a closet filled ONLY with prints and bright colors?
    Via ThinkStock
    Or have a closet filled ONLY with black clothes?
    Via ThinkStock
    Or have a closet filled ONLY with black clothes?
    Via ThinkStock

23 Of The Toughest “Would You Rather” Style Questions Ever

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Would you rather...
  1. Have a closet filled ONLY with prints and bright colors?
     
    vote votes
    Have a closet filled ONLY with prints and bright colors?
  2. Or have a closet filled ONLY with black clothes?
     
    vote votes
    Or have a closet filled ONLY with black clothes?
  1. Would you rather...

    Only own one pair of Yeezys?
    Via ebay.com
    Only own one pair of Yeezys?
    Via ebay.com
    Or own an unlimited amount of Skechers?
    Via skechers.com
    Or own an unlimited amount of Skechers?

23 Of The Toughest “Would You Rather” Style Questions Ever

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Would you rather...
  1. Only own one pair of Yeezys?
     
    vote votes
    Only own one pair of Yeezys?
  2. Or own an unlimited amount of Skechers?
     
    vote votes
    Or own an unlimited amount of Skechers?
  1. Would you rather...

    Wear yoga pants every single day?
    Via ThinkStock
    Wear yoga pants every single day?
    Via ThinkStock
    Or wear jeans every single day?
    Or wear jeans every single day?

23 Of The Toughest “Would You Rather” Style Questions Ever

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Would you rather...
  1. Wear yoga pants every single day?
     
    vote votes
    Wear yoga pants every single day?
  2. Or wear jeans every single day?
     
    vote votes
    Or wear jeans every single day?
  1. Would you rather...

    Be friends with someone who only wears trucker hats?
    Via us.asos.com
    Be friends with someone who only wears trucker hats?
    Or be friends with someone who only wears bucket hats?
    Via us.asos.com
    Or be friends with someone who only wears bucket hats?

23 Of The Toughest “Would You Rather” Style Questions Ever

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Would you rather...
  1. Be friends with someone who only wears trucker hats?
     
    vote votes
    Be friends with someone who only wears trucker hats?
  2. Or be friends with someone who only wears bucket hats?
     
    vote votes
    Or be friends with someone who only wears bucket hats?
  1. Would you rather...

    Go shopping with Audrey Hepburn?
    Via Keystone / Stringer
    Go shopping with Audrey Hepburn?
    Via Keystone / Stringer
    Or go shopping with Marilyn Monroe?
    Via Baron / Stringer
    Or go shopping with Marilyn Monroe?
    Via Baron / Stringer

23 Of The Toughest “Would You Rather” Style Questions Ever

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Would you rather...
  1. Go shopping with Audrey Hepburn?
     
    vote votes
    Go shopping with Audrey Hepburn?
  2. Or go shopping with Marilyn Monroe?
     
    vote votes
    Or go shopping with Marilyn Monroe?
  1. Would you rather...

    Wear a pair of these on a first date with a person you really like?
    Via infill3d.com
    Wear a pair of these on a first date with a person you really like?
    Or wear socks and sandals on a first date with a person you really like?
    Via Thinkstock
    Or wear socks and sandals on a first date with a person you really like?
    Via Thinkstock

23 Of The Toughest “Would You Rather” Style Questions Ever

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Would you rather...
  1. Wear a pair of these on a first date with a person you really like?
     
    vote votes
    Wear a pair of these on a first date with a person you really like?
  2. Or wear socks and sandals on a first date with a person you really like?
     
    vote votes
    Or wear socks and sandals on a first date with a person you really like?

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