I Wore My Boyfriend's Clothes All Week & Here's What Happened

When I started this piece and made the decision to wear a piece of clothing from my boyfriend’s closet every day, I thought it was going to be a piece of cake. Ushaia, my handsome and loving boyfriend (ily bb) was a bit resistant because of his love for fine suits and keeping his clothes unwrinkled. Unlike him, I typically can be seen wearing the same outfit three times a week and there’s also a high chance that by Friday my shirt will have some sort of stain on it. All that being said, he was hesitant to let me rummage through his closet until I found the outfit pieces of my dreams. 

I started on a Monday—a day that also happened to be the coldest day of the week—with a simple pullover sweatshirt from his closet. I should also probably mention that I bought this sweater for him for our anniversary. Needless to say, I was a fan already. 

I got dressed at 6 a.m. in all black, as one does, and went to my 8 a.m. class. Because most people were probably asleep and it was environmental science (sorry Prof) no one commented on the sweater that may or may not have been mine. After class ended I took the subway to my internship at Cosmopolitan.com and right away I got a few comments. My boss told me she loved my sweater and when I told her it wasn’t mine, she was surprised. Because it’s Cosmopolitan.com there was a photo shoot already set up so I asked the fantastic photographer, Reuben, to take my #ootd pic and he did not disappoint. 


A photo posted by Isabel Lara (@isabelcalkins) on

I paired my sweater with some basic American Eagle jeans and some booties and a bright lip to complete the look. It was casual and comfortable but still appropriate for the office. Day 1 was a success. 

Day 2 was a bit trickier. So tricky, in fact, that I only ended up wearing some of his cologne and didn’t even get photo evidence! I had my three other classes and two job interviews so I was trying to look as normal as possible. I didn’t want to show my ‘try it all’ attitude quite yet, might scare them away. 

Related: I Let My Brother Dress Me For a Week & Here's What Happened

On day 3 it was 75 degrees and sunny in Manhattan yet I had to go to Cosmo again and that meant I would be sitting in a heavily air-conditioned office. I paired one of my boyfriend’s work shirts with some classic American Eagle boyfriend jeans and my new Steve Madden heels. This look was a bit trickier because although my boyfriend is taller than me, (I’m 4’11 so everyone is taller than me but that’s a different story), the shirt was in between being long enough to be a shirt-dress and normal shirt. So I wore it normally but it kept untucking throughout the day... and I also kept sweating. I have no idea how men wear this kind of stuff all day every day. Once again I paired it with a bright lip because that’s my go-to outfit addition. I am a huge fan of Mac Matte lipsticks, I have like 15 different shades because I wear it everyday. 

The next day it was even hotter than before and I had a few breaks in between classes so I knew I was going to be outside for some of the day. But because of my logical fear of being cold, (I know I live in NYC, I am crazy) I wanted to layer up. I took one of my boyfriend’s hoodies that he wears to the beach (he's from Miami) and paired it with a classic Brandi Melville button up skirt with some simple white Adidas. This was my favorite look by far because I looked cute (at least I think so!) and I was comfortable both inside and outside. I got a few glances because the shirt was a little baggy on me and smelled like a boy, but still no one said anything. I am really starting to think that my boyfriend and I have similar tastes in fashion. 

Related: I Let My Boyfriend Style Me All Week & Here's How It Turned Out

On day 5, the last outfit for my week, I knew I needed to keep it simple. I had lots of homework to do so I would be inside and sitting. I took one of his t-shirts; I also think I bought this one for him. I paired it with some Urban Outfitters skinny jeans and booties. I added on a vest that I got from Marshall’s on top and that was that. The shirt was very baggy and the sleeves were too long but by Friday, I was so over it that it didn’t matter. Also, my boyfriend left that morning for Florida so I was kinda out of luck. 

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Overall, the only thing that really stood out to me about this week is that none of his clothes actually fit me. I cannot stress enough the importance of getting clothes that fit well, whether it’s a shirt, jacket, anything. Dressing in all oversized stuff for a week was comfortable somewhat, but it made me sweaty and by the end of the week I was seriously missing my own t-shirts. And my boyfriend didn’t like sharing too much. Sorry, not sorry. So am I going to wear his clothes again some other time besides to bed? Sure, why not. Will I consciously do it? Probably not. But at least now I know it’s an option!