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.

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