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Do You Know The Difference Between Pretty And Cool?

You know those formative moments when the whole way you view the world changes? I had one of those my freshman year of college. This is when I realized you could look good (great, even!) without looking pretty. This is when I learned the difference between pretty and cool.

I grew up in a world where pretty and preppy was the overwhelming ideal. It wasn’t until I went off to school a plane ride away from my childhood bubble that I realized there was an alternative to the look that never quite suited me. It wasn’t that I wasn’t exposed to cool style when I was growing up, but it was a hard thing for me to articulate. Like, I knew that Gwyneth Paltrow was so pretty with her pretty blond hair and pretty pink Ralph Lauren dress at the Oscars. I also knew that that ensemble definitely wasn’t something. Years later it clicked: sure, she looked pretty, but she definitely didn’t look cool.

When I arrived on campus, pretty was not the norm. There wasn’t a whole lot of the pink/bows/pearls I had grown up with. Girls wore a lot of black. They wore loose-fitting tops, edgy accessories, and other such things that were the antithesis of all I had been accustomed to. They looked cool, not pretty, regardless of their actual physical beauty. This changed my life! Cool is a thing I can strive for in my personal style. Cool is achievable and interesting and unique. Pretty is not. Some ladies do the pretty thing very well! I don’t. It looks too sweet, too saccharine, too too on me.

Pretty and cool don’t have to be mutually exclusive, but more often than not they are. Rei Kawakubo makes cool clothes. They are rarely pretty. Oscar de la Renta makes pretty clothes. They are rarely cool. But really, it generally comes down to styling. On its own, a Chanel tweed jacket is straight-up pretty. Style it with something quirky and unexpected like a Christopher Kane space dress and a Pamela Love talon cuff? The look as a whole instantly morphs into cool. Cool has a lot less rules than pretty does. Cool is about taking risks. It’s about juxtaposition. This is a freeing thing! Being pretty is much harder!

Anyway, my style evolved quite a bit during my college years. I learned that super skinny jeans and oversized men’s sweaters paired with an excess of costume jewelry and big glasses (my go-to look) wasn’t pretty, but it still looked good! But to further drive the point home, allow me to share a brief anecdote. I’ve worn glasses since I was 18 months old, and have worn nothing but plastic frames since middle school. It wasn’t until sophomore year that I went a little wild and got almost-comically big frames. A few months later, my mom asked me if I wanted to get another pair.

Not one to turn down some specs, I said sure, but asked her why she offered. Her answer? “You know, to get a pretty pair. I like the pair you have now, but they aren’t pretty.” My mom usually knows what’s up, so this was disconcerting! I politely explained that glasses were never, ever meant to be pretty — that’s what contacts are for. (Remember, we’re talking pretty in terms of style, not pretty in terms of beauty!) Glasses, obviously, could be cool though.

Of course, I can’t solely credit my location change for my fashion epiphany. Interesting fashion has become way more accessible in recent years. And this doesn’t make it any less cool! It just means the girls who have a tough time with the pretty have plenty of other options. And this is a very good thing.



  • Idylle Idea

    I love stylite, and this article is even more brilliant than normal!
    I’ve just started college and I’ve noticed exactly the same thing, though I’m finding it harder to give up the “pretty”! 

  • Tiffany

    This is so funny. When I was in high school I always tried to dress cool. For me that meant a lot of Ralph Lauren Polo, Nautica, and Tommy Hilfiger. This was the late 90s/early 00′s and I went to an all black high school. But I’ve always had a curvy shape so those things made me look like a linebacker. Once I embraced more feminine things I started to feel way more comfortable, and I look a hell of a lot better! 

  • Anonymous

     Great article,cool is the way to go.

  • Anonymous

     Great article,cool is the way to go.

  • saley50

     Iris Apfel is the epitome of “cool” as opposed to “pretty”.  

  • Kathy K

    This is probably one of the best things I’ve read on Styleite. 

  • Kathy K

    This is probably one of the best things I’ve read on Styleite. 

  • http://www.styleite.com Verena von Pfetten

    Yes! Exactly!

  • Anonymous

    Growing up in an urban NY setting, cool was the standard. The whole beatnik, black leggings thing was my mantra. Still is, to a degree. But now, it’s called cool, man, cool. I went thru a pretty phase for a nano-second but realized it just wasn’t me. Cool is achievable. Pretty’s way too hard to live up to on a daily basis. Besides, who wants to iron ruffles?

  • guest

     I am a fairly pretty woman, however, when I was in high school I had such bad acne that I felt very un-pretty. In addition to that I also was pretty poor and worked odd jobs to make money to buy clothes, which were always second hand from thrift stores. Because of these two factors I tried to dress cool and express my inner self rather than try to impress everyone else. The creativity I found through dressing is the reason I work in fashion today. By dressing for yourself daily in a way that you think is cool, makes the times you get dolled up pretty for someone else more special. 

  • Bethany Frissel

    I’m on the opposite side of this.  I’ve tried my whole life to be cool.  I cannot.  Cool is not in the cards for me.  So I aim for pretty, because I feel like it’s easier, and like it’s attainable for almost anyone.  Clean hair, a smile, and flowers.  All of my attempts at cool land in the world of ridiculous!

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