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Updated: Apr 19, 2016 @ 11:52 am
Nick Wiesner/Courtesy xojane

There is some sort of mystical street style lore about vintage tops. The "he/she wore vintage shirts" descriptor is one of those overly repeated tropes that is seemingly meant to connote bad-assery, a devil-may-care attitude, and effortless style.

I literally have none of the above traits. I spent last night Googling literary dog name possibilities and making red velvet cake pops from a Valentine's Day Pinterest recipe. Vintage t-shirts and the subtext of effortless cool isn't really my jam. So, in order to see how truly cool I could become in merely one week through the power of aged cotton, I decided to only wear true vintage shirts for seven days. The only rules were that the shirts and sweatshirts had to be legitimately "vintage," which I rather arbitrarily defined as over 10 years old.

Here's what happened.

Day One

On the first day I decided to wear an old favorite — a vintage purple Dinosaurs t-shirt that I borrowed (indefinitely) from my ex, John. Sorry for stealing so much of your clothing John, and also sorry for writing about it (twice...). 

Nick Wiesner/Courtesy xojane

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This shirt was a Goodwill find that is most likely from the early 90s — Dinosaurs originally aired from 1991 to 1994 — and it's one of those perfect old t-shirts that is indescribably soft from year after year of washing machines. This shirt even has small dryer holes dotting the sleeves and the hems, which only serves to make me love it more because authentic vintage, am I right? I wore it to work on a Monday and was actually shocked by the complete lack of reaction it received. It was only after work, at happy hour with a few coworkers, that a guy at the bar drunkenly slurred that he "loved my look." 

Was it because of the shirt? I ran away, so I guess I will never know.

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Day Two

On day two, I woke up to an unseasonably cold and gray day (silly unpredictable spring weather), so I decided to wear my friend Nick's vintage Duke sweatshirt, also from the early 90s. (Nick is also, coincidentally, the amazing photographer behind these photos). I didn't go to Duke, so I was slightly concerned about repping another school so blatantly, but no one took any note of my sweatshirt. 

Nick Wiesner/Courtesy xojane

I wore it with medium wash blue jeans and my favorite ankle boots, but given the very gross weather outside, I don't think anyone found my comfy look abnormal. I personally loved wearing a big comfortable sweatshirt to work — it made me feel cozy, but the vintage top made the sartorial choice seem deliberate and not lazy (at least, I hope it did!).

Day Three

For my third day of vintage looks, I decided to wear my father's old Cleveland Browns Champion long-sleeve shirt. I've seen my dad wearing this shirt in photos from when I was as young as five, so I have to assume it's from the early 90s, predating the whole Baltimore-Cleveland-Art-Modell-debacle. 

Nick Wiesner/Courtesy xojane

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When I asked my dad when he got the shirt, he was confused, and asked me when I stole it, as he barely remembered that he once owned it, so that was patently not helpful. This sweatshirt is an old favorite of mine — I've worn it notably while camping, hiking, and playing beer pong at a lake house — but it was certainly weird to wear it to work. I received a couple of comments, most notably from my boss, who asked me if I was a Browns fan. (I'm less into sports than maybe 99% of people I know, so he was understandably confused).

Most notably, it was really nice to wear something that reminded me of my dad all day because my dad is the best.

Day Four

On the fourth day I (hyperbolically) tempted fate and wore the most extremely unfashionable shirt I'd worn thus far. The early 2000's Clockwork Orange shirt I wore is not only a thrift store find but is also bright orange and a men's size medium. 

Nick Wiesner/Courtesy xojane

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I was uncomfortable and borderline embarrassed wearing the shirt, and I felt dressed for a hangover I didn't actually have (which, given that it is not completely unheard of for me to go to work slightly hungover, seemed like a waste of an outfit!). No one commented on my strange oversized t-shirt, but that was probably for the best because I would have cowered in the corner totally mortified if they had and would have blurted out something like "I'm doing this for an article I'm so sorry omg let's go to H&M right now!"

Day Five

Nick Wiesner/Courtesy xojane

On day five I decided to accessorize my vintage children's Costa Rica vacation shirt from 2001 with a tan leather jacket so I didn't look like a total psycho who inexplicably wore old t-shirts all week (yessss, I know that was kind of the point of this experiment, but it had definitely started to make me feel a little groddy by Friday). 

I can't lie, I was really over this whole "wearing actually vintage shirts" thing by this point.

Day Six

That's why, on day six (aka Saturday), I wore my late 80s Lacoste v-neck sweater, even though I very well knew that the acrylic material was sort of scratchy against my sensitive-as-all-hell skin. 

Nick Wiesner/Courtesy xojane

It was tailored, gosh darnit, and I wanted the world to know I still had a body underneath the shirts of so many different ages. As it was Saturday, no one really commented on my outfit. I spent the evening at dinner with a few friends and then ended the night with some casual drinks at a Williamsburg bar. I wasn't exactly comfortable the whole time (my skin was borderline freaking out by 9 PM), but I felt more put together in the sweater than I had in the sweatshirts and t-shirts I wore during the work week.

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Day Seven

I didn't do anything on Sunday except for clean, write, binge-watch House of Cards, and sleep, so I didn't wear anything (other than my PJs). I know, I know, I kind of failed. But lest you judge me for failing (again), my PJ shirt was from my high school graduation in 2007, so I'm pretty sure it counts.

So, what did I learn? I learned that despite editorial descriptions of what defines "cool" and "rockstar" styles, constantly wearing actual vintage t shirts — while occasionally comfy, fun, and personally nostalgic — isn't really my cup of tea.

Photo credit: Nick Wiesner