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

By Kelsey Stoskopf
November 26, 2018

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.

A Fact Finding Mission

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As a girl who rarely dresses up, except occasionally for work or a special occasion, my boyfriend has come to learn that it’s a miracle if he sees me in a wear with booties or my hair down.

Letting My Boyfriend Pick Out My Outfits For A Week

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

Day One: Super Bowl Sunday

Luckily, since he had no preference for either team this year, I didn’t have to wear a huge jersey. He picked out yoga pants, a jersey style shirt (bought in Minnesota), and Nike high-tops, which I hadn’t dug out of the closet in what seemed like years.

He Matches Clothes Better Than I Do

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

Day Two: The Beginning Of My Work Week

For the start of my work week, my Monday attire consisted of leggings and shoes I hadn’t worn in years. Maybe he’s trying to tell me something here. Are we getting at at something new?

Day Three: Inspiration From An Unexpected Place

The inspiration for this look came from Grease because we had watched it earlier in the weekend. He again picked certain items I hadn’t worn in years: my leather jackets, yoga pants, and black wedge booties. I’m beginning to see a theme.

Day Four: Another Day, Another Sweater

I guess it’s sweater weather, but I’m pretty sure I used up all of mine during this fun, experimental week. Seems like he likes the bundled up and comfy look? Sounds good to me.

Unnecessary Cruelty

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

Day Five: Another Inspirational Look For Thursday

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

Cat Lady Wardrobe

I sure got off easy with the cat-inspired wear though, because he almost dressed be in jeans and a denim shirt–a traditional cowgirl suit. There’s no way I would have been able to pull that off. The fashion gods were surely looking out for me.

Day Six: His Methods Were Improving

When it came to picking out my outfit each morning, he would lay out everything on the bed to see if it all looked good together. He would even stick the pants into the shoes to make sure the outfit all matched. Now that’s dedication.

He Likes The Sweater Look

If I’ve learned nothing else from this experience, it’s that my boyfriend likes me in sweaters, yoga pants, and boots (at least in the winter). And I’m definitely not complaining.

Day Seven: Our Journey Comes To An Early End

Shutterstock / Dean Drobot

As day seven rolled around, he gave up. He threw in the towel, waved his white flag, and forfeited. What he lost, I’m not sure. Even though my boyfriend is undoubtedly better at matching and picking out clothes than I am, he said he hated choosing my outfits since “I had nothing cute to wear.” Time for a shopping spree?

Some Lessons Learned

Taylor Schmidt

At least I learned a few things from this journey, despite its abrupt end. The most important lesson is my boyfriend would rather eat, play video games, work out, or do absolutely nothing than worry about what I’m wearing. And maybe that’s for the best.

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