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

Photo: courtesy of the author
i let my dad dress me for a week

I traveled around the world for three years, and now, I’m living back at 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 of it off to move out again.

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

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

So, I was pretty interested in the kind of 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 with no commitments. He shuffled over to my closet and started sliding around the hangers.

He pulled out a tan, button-up romper covered in flower 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, either.

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

Day 2: Dress For Me A Party

It was party time and I hoped my Dad would pick something that I wouldn’t feel totally embarrassed in. 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 that I did have one hat, and rummaged through my closet to pull out a black turban that I bought from China. He took one look at it and said, “I can’t imagine that hat with anything... Well, I guess this hat will work since it’s all that you have.”

The hat was actually the only thing I liked about this outfit choice. As soon as the party was over, I took that dress and donated it — 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, letting me know that, “I’m feeling blue jeans today.”

Sadly for him, I don’t own a single 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 that I got on sale at a store I can’t even remember the name of.

“Would you wear this?” he asked.

“No,” I replied.

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

I told him that I obviously would wear the shirt separately, but not together with the jeans. Then, as I looked in the mirror, I started to realize that I HAVE worn this outfit before. It was the kind of frumpy get-up that 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.

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 real 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" that I could drape over my shoulders. He thought he was going crazy and then 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 I only wore it once to a funeral. The dress was cute, but I don’t think I would ever wear it on a date. Nice try, Dad.

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 then said, “Well, I wanted to choose jeans but those jean shorts 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 him why he chose that skirt, his reply was, “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, one that I actually wear all the time. It was a hand-me-down from a friend (actually, 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 black skinny 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. 

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