Style Me Struggling

If you know me well – and perhaps if you’ve been following this blog at all – you know that I have a sort of ridiculous amount of trouble getting dressed in a very basic way.  I am well known by my fiancee and college roommate for wearing my famous “I can’t figure out what to wear today” outfit: starting from the bottom and moving up, we have slippers, socks, underwear (that’s right, no pants), and my Vassar sweatshirt.  Depending on how cold it is, I might also be wearing a hat.  It’s sort of like this picture, minus the sunglesses, and in just socks, slippers, and underwear.  To be completely honest, it’s usually just one sock.  I’m not sure why.

also, i'm usually not in a car during this process.

Sometimes I think I have spent so long working in the veterinary field because I know what I’m wearing every single day: scrubs.  They are comfortable, they are interchangeable and all match each other, and they require no thinking whatsoever when getting up in the morning beyond, “Is this clean enough to wear?”  Yes, I just admitted that to the general public.

When we were little, my sister and I were polar opposites when it came to clothes. I’m really, really sorry I don’t have pictures to illustrate my point, but here it is: While my sister spent a good couple of months (at least!) insisting on wearing her pink headband and her pink necklace and frilly dress or other nice-looking clothes, I wanted something that was comfortable, and I would happily wear it every single day until my mother made me wear something new.  I didn’t care how it looked, as long as I felt good.  My sister, on the other hand, wanted earrings so badly that she wore the clip-ons until her ears turned red (my mom finally decided that if she wanted them badly enough to put up with that pain all day, she could probably handle actual piercings).  In retrospect, my attachment to comfort rather than style, and my pleasure in wearing the same thing until it was taken away, probably factored into my not being one of the popular girls.

Now that I’m all grown up… not much has changed.  I still don’t want to wear anything uncomfortable – at all.  I find a pair of shoes that fits and those are the shoes I will wear until they are dead.  I don’t do well with heels, no matter how pretty they are.

The problem is, I have no idea what my sense of style is.  Sometimes I feel attractive and confident – but it’s often in completely different kinds of clothes, and I can’t find a pattern, and I have no idea what I want to wear.  Case in point: Today we went to a consignment shop and I bought a very pretty dress.  It looked lovely on me, and I know I’ll wear it a lot.  It is kind of like this one:

see? i can look nice in a dress!

Now, in the exact same shopping trip, I bought pants and a shirt from the guys’ section.  And I look and feel totally hot in them, if I do say so myself.

Here is a picture of me dressed in my (male) friend’s clothes, feeling totally attractive (though I realize I didn’t look as good as I felt – and also this was about 5 years ago):

dressed as my awesome roommate for a costume party in all his clothes - convincingly, if i may say so

I am perplexed.  How is it that I love feeling dykey in my boy’s jeans and polo shirt AND I love feeling pretty in my dress?

I mean, yes, I know that this is totally allowed, but I have no idea where to start looking for something to wear when it’s time to dress up: a button down shirt? A dress? A button down dress?  I can’t figure out what I’m entirely comfortable it  – sometimes it’s the dress, sometimes it’s the pants.

And don’t get me started on shoes.  If I can wear Chacos with it, I’m happy, and if I can’t, then I am lost.  As Kate commented yesterday, “Just because we’re girls doesn’t mean we can’t fail at footwear. Shoes are hard!”

Does anyone else have this complete fashion struggle?  This is why I am wearing a suit and a dress at my wedding.*  How do you know what your “style” is? How many of you spend a good chunk of time in your socks, slippers, and underwear throwing various clothes around the room? What is the key to looking good and feeling comfortable, if it is even possible?

*I ordered those shoes I liked! The ones that you all said you liked too!  But, um, they’re heels, so we’ll see what happens.  They shipped today! Look at me, being all decisive.
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