There are many things I am terrible at - but one of the ones that fills me with the most self-doubt is the fact that I do not know how to dress myself.
I don't know how I missed this particular boat, but I did and so here I am - precariously close the age of 30 without the knowledge of how to make clothes work.
I will say that I am trying. In the past few years I have made a concerted effort to try more than I ever have. I try more now than I did in New York. New York was over my head and not in my budget. My poor feeble-minded mind could barely wrap itself around RCN bills - and I once spent $30 on a tank top. A. Tank top. Granted, I still own and love it. But $30 then was a whole week's worth of lunch and dinner.
I have this vivid memory of visiting New York when I was still living in Maryland and seeing a tee-shirt for $29 in Dylan's Candy Store. My mother and I were aghast. $29 for a tee-shirt?! Who would ever pay such a price? Me (it turns out).
Anyway - I am finally at a point in my life where I not only have some expendable income to put towards my wardrobe, I also have developed a sense of giving a sh*t. Its weird and I'm trying to embrace it, but man it is a struggle.
Back in the day, my fashion of choice was always a funny tee-shirt and jeans. Always. I don't know why I never thought to try any harder than this. But I was happy in my tee-shirts that were essentially wearable comedy bits.
PS - I still own most of my favorite tee-shirts. I cannot bring myself to get rid of them despite the fact that I am trying extra hard to move onto bigger and better things. Some day I might become a hobo again and I at least want to be a funny hobo.
Now that I am making a conscious effort to see beyond the tee-shirts, I am running into some problems. First of all, I immediately hate everything that doesn't look like it like it came directly out of Grace Kelly's closet. My "style" can only be described as classic meets impractical meets out of your price range.
And so I am left just trying on everything, which then becomes trying on nothing because when you go into a Forever 21 or Urban Outfitters, everything can be super overwhelming. Also, primarily atrocious. Which is why when things like skinny jeans and leggings started being propagated at these stores - I resisted. Hard. These were the people who tried to also get me into bubble skirts and vests. They were not to be trusted.
Turns out skinny jeans and leggings are both excellent wardrobe staples that should be accepted and appreciated for their value of making your legs look longer and making it so you can still go on the monkey bars in skirts. If they were right about this, what else were they right about?
I've started trying to find out and its hard. Example - I need a wide brown leather belt to wear with a few different dresses I already own. I've made it past the first step - I know I need the belt, now I have to figure out where the eff to buy it and what it is supposed to look like.
I've developed this idea in my brain of "wide brown leather belt" that may not actually exist in the known universe - and if it does, I'm not sure I'll know it when I see it.
This example can also be used for just about everything - including but not limited to black knee-high boots, button-down shirts, and skirts that fit a bill more varied then "its too hot for pants."
So, I've decided that I either need to start living with girls who will tell me what to wear again, or hire a personal shopper. Or maybe just go back to the tee-shirts.