I Let A Teenage Boy Dress Me For A Week

A few weeks ago, I let my 16 year old sister dress me for a week. It was a fun experiment, although it definitely had its pitfalls: some days I was uncomfortably chilly, I felt kind of silly in a really big hat, and one day I was forced to wear a crop top. Overall, even though it wasn't easy giving up control of my wardrobe, it was worth it to see my clothes through another person's fresh viewpoint.

I guess that's why I decided to do it again. This time, I put my teenage brother in charge of the week's outfits. Kieran is 15 years old and, like most of his friends, he likes to spend his time playing video games and wears a typical uniform of t-shirts and jeans. However, he's also into art and has excellent taste in sweaters.

So I had a feeling that he wouldn't just put me in the same T-shirt and jeans all week, although I was curious to see just how adventurous he would get with his 25 year old sister's closet. For the record, my closet contains around 20 pairs of heels, several rompers and jumpsuits, and a ton of dresses — in addition to more normcore items like jeans, tees, and sneakers.

While he picked out my outfits, I was careful not to give him any direction, other than mentioning what I would be doing that day.

Here's how it all went down.

Day 1

The first day started off simple and easy. Kieran picked black skinny jeans, a grey T-shirt, a white sweater, and Converse. This was a comfy and warm outfit for hanging out at home and running errands; nothing fancy, but I felt good in it. I would happily wear this outfit during a normal week (and probably have).

Day 2

I did NOT love this next outfit. I go to a few workout classes during the week and therefore asked Kieran to pick out an outfit for me to wear to my kettlebells class. Since I work from home and my fitness classes are in the evening, I have no problem wearing a workout outfit all day. He picked out black leggings, my one pair of Nike sneakers because it was the only option, and... this top that I could have sworn I hid deep inside the back of my drawer.

Yeah, my mom bought this tank top for me and I have literally never worn it. I don't generally like wearing clothes with text on them (this shirt is the one exception) and this top is a perfect example why: the text is usually really dumb. "Just working on my fitness"? Really? I think if I'm in a gym lifting weights and running laps, I don't need my shirt to spell out exactly what it is that I'm doing. Plus I never wear hot pink.

I felt kind of lame wearing this shirt to my kettlebells class but since nobody came up to me and sarcastically said, "Oh is that what you're doing?" I have to admit that I was probably the only person overanalyzing my shirt.

Day 3

The next day was another quiet day of working at home and taking my dog to the vet. Kieran picked out boyfriend jeans, a striped button-down shirt, my Clueless sweater, and loafers.

I liked this outfit a lot, even though nobody at the vet seemed to notice my awesome Clueless sweater and even though I have to admit that these are not the most flattering jeans that I own.

Mostly I was just really impressed with Kieran's idea to match the sweater with a patterned collared shirt. Bold, and super cute too.

Day 4

The next day I was planning to go out to dinner with some friends. Kieran had me wear a teal tank top, a flowing black cardigan, black leggings, my yellow coat, and gold sneakers. I wasn't sold on wearing the yellow coat with the gold sneakers, plus the teal top — altogether it seemed like a lot of color at once for me. But I think he made the outfit work by grounding it with the black pieces. It was definitely very visually interesting.

I added a gray-brown lipstick that he disapproved of but I told him he wasn't allowed to pick my makeup, so there.

Day 5

I had another workout class this day, so Kieran had me wear black leggings again (a different pair, of course), my Nikes, and... the other workout top my mom bought me that I previously refused to wear. Yeah, she gave me two of these. I think there was a sale. This one says "Push your limit," which definitely isn't anywhere near as annoying as the first shirt. Plus it's not entirely hot pink. So I wasn't too mad at this outfit overall.

It did make me realize that boys don't really have to take body hair into consideration when planning outfits, though. This was the second time this week that I had to make sure my armpits were shaved, which is not my usual mode of operation in the winter. I had no idea why he kept picking tank tops when I had a ton of long-sleeved workout tops. I comforted myself with the fact that at least I didn't have to shave my legs.

Day 6

I was going out to dinner with my boyfriend, so I told Kieran to pick something nice. I was expecting a dress, or maybe even a skirt, with high heels. Instead he chose a long-sleeved black silk top, black pleather pants, a leopard print purse, and my yellow coat and gold sneakers again.

While not what I would have chosen for date night, I still liked this outfit. For one thing, it was warm. For another, I thought it was cool that he made the mostly black outfit have visual interest with the different fabrics of silk and pleather, and I liked the fun touch of leopard print.

By this point it was pretty obvious that my brother is obsessed with my gold sneakers and yellow coat. When I asked him which coat I should wear, he replied, "The yellow one, duh."

Day 7

This was the last day of the experiment and I had a yoga class to go to. Once again Kieran had me wear my Nikes and a pair of black leggings. In his defense, these are the only non-fashion sneakers I own. I cannot, however, defend his obsession with black leggings. I own many other kinds of workout leggings and pants, in colors, I swear!

The good news is that he finally picked a top with sleeves and without any inspirational text. I felt comfortable wearing this outfit to my yoga class and to do errands; it wasn't the most fashionable outfit ever but it didn't make me stick out either.

At the end of the week I asked my brother what he thought of the experiment. He said he had fun picking out my clothes for me and that he was happy to help me by, I quote, "pointing your style in the right direction." Um, thanks, little bro.

When I asked him why he didn't pick out any heels for me to wear, he said he wanted me to be comfortable. Then I asked him why he didn't pick out any dresses or skirts and he said, "Because it was freezing!" I inquired as to whether he knew about the existence of fleece-lined tights. "Oh. No. I didn't know if you had those."

So basically, he explained, he picked outfits that he thought would be comfortable and that he would wear himself if he were me. The outfits were all really comfortable, but I was also surprised and impressed by how stylish some of them were as well. His age showed in some of his choices, specifically when it came to his weakness for inspirational text and shiny sneakers. But Day 3's outfit and Day 6's outfit were particularly well put-together, I thought.

Turns out that having a 15 year old boy dress you isn't so bad. Who knew teenage boys were so considerate and stylish? Or maybe I just got lucky with my brother. When he's done playing video games I'm going to go ask him if he might consider a career in fashion.

Images: Kelly Dougher