My Boyfriend Chose My Outfits For A Whole Week & The Effect Was Amazing

It was a Monday morning and I tore my closet to shreds looking for an outfit to wear that wasn’t totally predictable. Everything was too short, too tight, too wrinkled, or too boring and I sat on the floor wishing that I could go back to my private school days when I sported a plaid uniform five days a week. In a moment short of a mental breakdown, in absolute desperation, I propositioned my boyfriend into dressing me and I have to admit, it was an awesome experiment.

  1. It was clear that he didn’t notice my insecurities. My go-to jeans are high waisted. I hate feeling my love-handles roll over my jeans, and when they rest on my hips, I spend the majority of the day hiking them up. This always results in some weird camel toe situation. Not only did he pick out hip huggers (ugh), he had me showing off my arms almost every day of the week. I wasn’t thrilled and felt the need to hide whiskey in my coffee mug to feel comfortable, but as if it was some form of exposure therapy, I got used to it. He showered me with compliments and couldn’t keep his hands off of me, so that helped.
  2. Apparently, he loves me in literally anything. This is nothing short of an adorable realization. His choices ranged from post-workout Barbie (leggings as pants) to Pretty Woman (a mini skirt with knee-high boots). His style was absolutely all over the place, but somehow it worked. His face lit up like a mad scientist when his pairings came together and I had to remind him that we were only doing this for a week. I also had to remind him that he couldn’t quit his day job to audition for Project Runway. I’m not a dream crusher, but he can’t even thread a needle.
  3. He found clothes that I didn’t even realize I had. At first, I literally thought that he went to the store and bought something for the sake of this experiment. I’m embarrassed to admit that there are clothes hanging in my closet with the tags still on. In my defense, I have this veil of confidence when I’m in the dressing room, but when I get home, I’m never bold enough to actually wear it. What’s the deal with magical dressing room mirrors? It’s like looking at yourself through a Snapchat filter. But when my “stylist” (as he confidently called himself) forced them on me, I was shocked to learn that I felt confident even without the magic mirror.
  4. He took me out of my comfort zone. Like, way out of my comfort zone. If my comfort zone was Earth, he was dressing me out in Pluto – a planet of boldly dressed Martians. A crop top with high-waisted pants? Fine, but I’m not eating all day. I work in a casual environment, but I’ve never had the guts to step outside of my “jeans and a button up” box. It was like dressing Audrey Hepburn in ripped jeans and a Metallica t-shirt.
  5. Other people were digging his choices. I hardly ever get compliments on my style because it’s super predictable. My coworkers could win big money in Vegas if the bets were on my outfit choices. I didn’t tell a soul that I was trying out this little experiment, so any mention of my style was totally unsolicited. I didn’t tell my “stylist” that his work was a hit because there wasn’t room for that kind of ego in our tiny apartment.
  6. “Your hair is your most important accessory.” Those words actually came out of his mouth. I created a monster but dammit, he was right. My hair is always an afterthought in my morning routine. Honestly, I just can’t be bothered at that point because I’m always rushing out the door. He told me that he loves everything from bouncy curls to beach waves, but what he didn’t comprehend was the work behind them. I got up a little early, dusted off the curling iron and got to work. HE WAS SO EXCITED.
  7. Speaking of accessories: guys don’t care. Once he had me dressed and ready to go, thrilled with his handiwork, I had to remind him that I needed a necklace and earrings. “Really, though? I feel like it’s a little much.” This was like a dagger through my heart because accessorizing is the only part of getting dressed that I actually enjoy. He humored me by picking out a pair of studs and the thinnest necklace ever created. It was like wearing a string of floss around my neck for a week.
  8. Apparently, he actually notices what I wear. My assumption has always been that my boyfriend couldn’t remember a single one of my outfits if his life depended on it. I was so wrong. He pulled clothes out of my closet and placed them into a neat pile on the bed. When I asked if there was a bedbug infestation or if he was kicking me out he simply said, “You wear these almost every week and I want to pick out something new.”
  9. He thought of things I’d never considered and my mind is officially blown. He knew that my staff meetings always fell on a Wednesday, so when Tuesday night rolled around, he was laser-focused on finding an outfit that would make me feel confident. He picked out a relatively sexy lace top, for which I gave him a death stare, but then threw a blazer at me. “Just because you’re running a meeting doesn’t mean that you have to dress like my grandma”. Point taken. On Friday he said, “You need a pair of tan heels to tie this outfit together.” I’m sorry, did Tim Gunn just waltz into the room and inhabit my boyfriend’s body? Also, did he just ask me to buy yet another pair of shoes? Yeah, I’ll marry this guy for sure.
Caitlyn is a freelance writer living in Washington D.C.