I'm Determined to Get In On This Baseball Cap Trend Even Though Hats Frighten and Confuse Me

You know those looks that you love on other people but can’t figure out how to incorporate into your own day-to-day life?

Apr 24, 2014 at 9:00am | Leave a comment

You know those looks that you love on other people but can’t figure out how to incorporate into your own day-to-day life? Do they eat away at your soul like they do mine?
 
For instance, I love bright pink lipstick but I just don’t know what to do with my face when my lips are painted neon. Here I sit, day after day, scrolling through my Instagram feed and seeing dozens of seemingly normal humans pulling it off, and yet when I try it, my face morphs into perma-duck face. I’m just not used to it, but I’ve promised myself I’d ease into it this season (stay tuned if you like to laugh at the misfortune of others).
 
However, my biggest issue is hats –- specifically baseball caps. And by “issue” I mean, “thing I so desperately want to conquer and need to figure out because I am a grown women and I can do whatever I want.”
 
I own exactly three hats (plus a couple that I stole from friends years ago so I guess they’re mine now) and I never wear them because I’m too scared and confused by them. I am literally too chicken to wear a hat. I know it’s just a thing that sits on your head and protects it from the sun (shout out to sun safety) but I’ve always found it pretty hard to wear one and not have the hat wear me.
 
The only time I actually wear a hat is when I’m on vacation but that’s because I don’t want my brain to fry underneath the sweltering sun, and also because I’m in vacation mode and am therefore fearless and drunk in love for two weeks. 
 
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Exhibit A. Melting in insane heat in Rome / melting in the presence of this puppy.

 
That being said, seeing as how sportswear is officially the chicest trend for the summer (according to me…) it’s about time I figure this out. I refuse to let another beautiful trend pass me by (military jackets, we will meet again someday). For now, I want to start with the hats I have in my closet and begin to incorporate them into my everyday wardrobe. Here’s what I’m working with:
 
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Eventually, I’m hoping to look less scared when I wear these. 

 
Once I get more comfortable in these three, I’ll branch out into the baseball caps that have been calling my name. My strategy is simple: Find hats that are too damn cute to leave behind. If I’m going to do this, I aim to be in statement hats like the ones below by the time summer rolls around. And so, I present to you my ambitious (yet affordable) wish-list: 
 
 
Are you a hat connoisseur who wants to impart some wisdom and advice upon me? Your advice is not allowed to be “brush your hair” because OH MY GOD MOM, MESSY HAIR IS KIND OF MY THING, OKAY? Also, what trends do you need help conquering?