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I Let My Boyfriend Dress Me For A Week, I Never Thought This Would Happen

By Kelsey Stoskopf
Flamingo Images

Whether we like wearing yoga pants and a t-shirt or dresses every day, sometimes our style doesn't always line up with what our significant other likes to see us in. I set out on a mission to see what my boyfriend of two years really likes me wearing and this is what I found out about his preferences, style and our relationship. The only two rules were I couldn't change the outfit he picked and I couldn't let him know what I thought about it.

I set out on a very eye-opening mission.

Taylor Schmidt

As a girl who rarely dresses up, except for work or a special occasion, my boyfriend has come to learn that it's a miracle if I'm caught wearing a dress with booties and my hair down. 

I Let My Boyfriend Pick Out My Outfits For An Entire Week.

But he learned from very early on that loving me meant loving my minimal makeup, hair in a bun, yoga pants and t-shirt look. Despite my signature look, I decided I wanted to learn what he actually liked me wearing.  

Day One: We Started This Journey On Super Bowl Sunday.

Luckily, since he had no preference in either team this year, my wardrobe was not decked out in Bronco orange or Panther blue. He picked out yoga pants, a jersey shirt (which he bought me in Minnesota) and Nike high tops, which I hadn't dug out of my closet in years.

I Learned He Matches Clothes Better Than I Do.

Needless to say he sure doesn't mind the yoga pants that I'm always wearing and he seems to like me wearing things he buys. And, for a guy, he has great matching skills.

Day Two: The Journey Continued Through The Work Week.

Again for my Monday attire, he picked leggings and shoes I haven't worn in years. Is he trying to tell me something here? Maybe we're getting at something. 

Day Three: He Even Got Inspiration For My Looks.

The inspiration for this look came from "Grease" (maybe because we had watched it earlier that weekend.) Again a piece of clothing I haven't worn in years, my leather jacket, yoga pants and black wedge booties. I'm seeing a theme now.

Day Four: Another Day, Another Sweater.

I guess it is sweater weather, but I'm pretty sure I used up all of mine during this experimental week. So he likes the bundled up and comfy look? Sounds good to me!

But Sometimes, He Was Just Cruel.

A bunch of snow on the ground? Sure, let's make her wear wedged boots. Sounds like a fabulous idea. Ugh, guys just don't understand the struggle some shoes cause, especially in the snow!

Day Five: Another Inspirational Look Came On Thursday.

This look he called "Tabby Thursday" or in other words, "How To Dress Like A Cat Lady: 101." He switched it up and chose jeans and paired them with my cat shirt and cat Vans. He's definitely not ashamed of my love for cats. 

The Cat Lady Wardrobe.

I dodged a bullet on this day though, because he almost put me in jeans and a denim shirt. There's no way I could pull that off. The fashion gods were sure looking out for me. 

Day Six: His Methods Were Even Better Than Mine.

When it came to picking out my outfit, he would lay everything out on the bed to see if it look good together. He would even stick the pants in the shoes to make sure the outfit matched. Now that's dedication. 

It’s Sweater Weather.

If I learn nothing else from this experience besides one thing, it would be that he likes me in sweaters, yoga pants and boots (in the winter, that is.) And I'm definitely not complaining. 

Day Seven: Our Journey Came To An Early End.

Day seven rolled around and he gave up. I mean he threw in the towel, waved his white flag and forfeited. Despite being better at matching and picking out clothes than I am, he said he hated choosing my outfits since I had nothing cute to wear. Shopping spree?

A Few Lessons Learned.

Taylor Schmidt

At least I learned a few things from this journey, despite its abrupt end. The most important lesson? He'd rather be eating, playing video games, working out or doing absolutely anything else besides worrying about what I am wearing. 

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