I Let My Dad Dress Me For A Week And Turns Out, Father Doesn't Know Best

Photo: courtesy of the author
photo of author dressed up by her father

I traveled around the world for three years, and now, I live back home with my Dad in his basement. Yes, it’s the typical millennial scenario of coming home to face a mound of college debt while creepily dwelling in the dingiest part of my Dad’s house until I pay enough off to move out again.

But it’s not all that bad, and I like my setup here. I’ve missed much time with him while traveling, so I thought letting him into my life and wardrobe would be a fun idea. While he didn’t exactly feel the warmth and fuzzies at his opportunity to pick out my outfits, I feel like he liked it, at least a little. 

I’ve got to say; my Dad has his own unique “style” consisting of jeans, moccasin loafers, and t-shirts that he cuts the sleeves off of (if he’s even wearing a shirt). 

So, I was interested in the outfit choices he would pull out of my closet.

Here's what happened when I let my dad dress me for a week:

Day 1: Dress Me For A Normal Day

The first day, I asked my dad to dress me for a normal day without commitments. He shuffled over to my closet and started sliding around the hangers.

He pulled out a tan button-up romper covered in floral prints. It’s one of my favorite outfits and one that I bought from a vintage store in Melbourne, Australia.

Why did he choose it? Well, because he thought it looked "comfortable" and "easy."

While holding it up, he looked at it with a confused expression. “Is this the front or the back?” he asked. I’m pretty sure he didn’t even realize it was a romper.

Overall, this is an outfit that I wear all the time because it’s super cute, easy, and comfy! Good job, Dad.

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Day 2: Dress For Me A Party

It was party time, and I hoped my Dad would pick something I wouldn’t feel embarrassed about. As usual, going for the easiest choice in the closet, he picked out a long striped dress with a built-in, sleeveless crop top. It was a hand-me-down from my sister and was not flattering on my pudgy tummy AT ALL!

He did make an effort to try and dress it up.

“Do you have a white sweater?” he asked. No, I didn’t.

“Do you have any hats?” he asked.

I told him I had one hat and rummaged through my closet to pull out a black turban I had bought from China. He looked at it and said, “I can’t imagine that hat with anything... Well, this hat will work since it’s all you have.”

The hat was actually the only thing I liked about this outfit choice. As soon as the party was over, I donated that dress — my pudgy tummy will remain hidden from here on out.

Day 3: Dress Me For Work

Letting my Dad dress me for work could have been disastrous, but I allowed it to happen anyway. Now familiar with my closet, he started cruising through the hangers, telling me, “I’m feeling blue jeans today.”

Sadly for him, I don’t own a pair of blue jeans, so I pulled out a pair of skinny black jeans from Kohl's. Looking for a top, he found my olive green, long-sleeve t-shirt I got on sale at a store I can’t remember.

“Would you wear this?” he asked.

“No,” I replied.

“Then why do you have it in your closet?” he mumbled.

I told him I obviously would wear the shirt separately but not the jeans. Then, as I looked in the mirror, I started to realize that I had worn this outfit before. It was the kind of frumpy get-up I’ve worn hiking or, most recently, under my snow pants and jacket on a dog sledding trip.

Overall, the outfit was frumpy and unflattering, not something that I felt comfortable wearing to work.

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Day 4: Dress For Me A Date

It was date night, and I couldn’t wait to see what my Dad would choose for the big event.

“Do you have a straight jacket?” he asked. He’s a really funny guy.

He started looking through my closet and asked, “Are these all the clothes you have?” He started to dive deep into my boyfriend’s section of the closet, apparently not realizing the difference in size, color, and gender genre.

I redirected him, and he started a mad search through my items, swearing that he saw some "thingy" I could drape over my shoulders. He thought he was going crazy and pulled out a tiny plaid jacket.

Realizing that it didn't go with the flowy, floral dress that he picked out, he put it back and handed me the dress, a little defeated. I got this dress as a hand-me-down from a friend and only wore it once to a funeral. The dress was cute, but I don’t think I would wear it on a date. Nice try, Dad.

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Day 5: Dress For Me A Concert

After finding a few stacks of summer clothes in my closet, I gave my Dad more choices to pick out my concert attire. He gave my jean shorts a good once over but said, “Well, I wanted to choose jeans, but those jeans are way too short.” No surprise there.

He finally settled on a long black skirt from H&M and a polka dot crop top and sweater from Forever21. When I asked why he chose that skirt, he replied, “I chose the long skirt because it looks like something that you would wear to Woodstock, which is a concert.” (Yes, I know that. Thanks, Dad.)

I actually liked this outfit because it was cute and comfortable, but it probably wouldn’t be my first choice for a concert.

Day 6: Dress Me For Sightseeing In The City

I was spending the day sightseeing around Philadelphia (the closest city to my hometown) and asked my Dad to find a good outfit for me.

He pulled a blue, flower-print dress out of the closet that I wear all the time. It was a hand-me-down from a friend (the same friend that gave me the flower dress I wore on date night), and he said, “This just jumped out at me...I’m going for an Annie Hall look. She always wore cool stuff. You would like it.”

I did like it, even though I still don’t know who Annie Hall is. Oh, and although he expressed that he hated my turban hat, he still chose it as the leading accessory for my sightseeing outfit.

Day 7: Dress Me For Going To Class

The last day required my Dad to choose my outfit for class. For this, he seemed to have a vision.

“I’m looking for a plaid button-down and jeans.”

I pointed him in the direction of the shirt that matched his description, but when it came to jeans, all I had were the skinny black jeans from the work outfit.

“The point is, we NEED jeans,” he said.

At the last minute, he set his eyes on a pair of tan Capri pants and whipped them out instead.

“Let’s see what this bad sucker looks like,” he said. That bad sucker? It looked... pretty bad. The whole outfit didn’t really match and was unflattering overall. "A" for effort, though.

I let my dad dress me for a week, and it wasn’t all that bad. Looking back at his outfit choices, I’m not surprised by how mellow and conservative they ended up being. 

All photos: Author

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Shannon Ullman is a freelance writer and journalist who has been traveling the world for over 10 years.