I’ve seen this challenge online and always thought it looked fun, so I figured I’d give it a go! My boyfriend, Tyler, was on board so we picked a week and let the experiment unfold. He was thoughtful and would double check the weather for the day and ask if particular clothes were warm or if certain shoes were comfortable. I was impressed! I was nearby as he picked out the outfits in case he has questions where things were. I got a laugh when he paused after starting the first night and said, “wait, do I have to pick out your bra and underwear, too?” I told him I’d handle the undergarments, so he didn’t need to worry. There was definitely a look of relief as he smiled at me and continued going through my closet.
I think he did pretty damn well, if you ask me! But see for yourself…
The first day was Monday and I was back to work. He put together Monday’s and Tuesday’s outfits on Sunday night before we went to bed. He spotted this flannel first thing and decided to start from there. He exclaimed, “I’m going to dress you like me for the first day!” Next he found the “dibs on the drummer” shirt and chuckled as he selected it. Then he went with black jeans and some fancy knee high socks for added warmth. Tyler noticed my bin of shoes that I’ve yet to find a place for and rummaged through that until he found the wedge, spiked sneakers that he settled on. He was admiring his work hung up together and then said he wanted a scarf and asked where those were. I pointed to their location and he went through several before deciding on a black scarf with white cameras on it. I thought we were done with this outfit, but he went out to the hallway closet and got my tried-and-true (p)leather jacket and told me this was for tomorrow, too, because he knows how cold I get, but didn’t want me to wear my Northface jacket.
The starting peice for this outfit was the cross cardigan. He pulled that out immediately and started going through shirts to go under it. I expected just a tee, but he actually pulled out a red and grey flannel. Then he said he wanted this one to be a little more dressy for work, so he asked where my work pants were and I pointed to the drawer. He pulled out the first pair and I let him know that those were capris, so he went for the next one and settled on those – black, skinny pants from Forever 21. Lastly, he needed some shoes and went through a few and visited several locations of the house to look at the selection before bringing back some ballet flats that I bought when I worked at Macy’s at the cosmetic department. He asked if they were comfortable and I told them they were. And then he asked what kind of socks do I usually wear with these shoes and I chuckled and told him that I didn’t. He expressed that my feet would be cold, though, without socks! I reassured him that as long as there’s not snow on the ground, these shoes were fine without socks. He said okay and put that outfit in it’s location so I could put it on in the morning.
For Wednesday’s outfit, Tyler saw that it’d be colder out and decided a beanie was a must. After going through my hats, he chose a purple one. Next, he went straight for a galaxy print scarf that he got me. He wondered about pants and I reminded him that jeans were allowed at my job. He dug through the dresser and found some black and grey skinny jeans. Then Tyler grabbed the short combat boots he had almost picked on Monday for that outfit. Last was a shirt. He pondered our loud what color would go and settled on a long sleeved grey shirt. He spotted a purple cami and threw that on the pile, as well. So far, this is my favorite, but that could be because it’s got a lot of purple.
I was completely absent when Tyler picked out Thursday’s outfit. He had told me there was a STL Blues game on that night, but I didn’t connect the dots until I got home and saw what he had laid out. I just went “ohhhh,” because I should’ve seen it coming. I liked his choices and that it was still stylish while being sporty. Can’t beat that! Oh, and my hair is red now. :D
On Friday, Tyler and I drove up to Chicago for our little weekend away, so Tyler made sure my daytime look could easily transition to our plans of seeing a concert for the night. I just had a regular black tank top on and buttoned the flannel up for work. We were going to the Bottom Lounge to see I the Mighty and Hands Like Houses perform, so I told him to try to make me look show-worthy. He had started with the purple flannel, then some jeans, and combat boots. He took his time looking through my tops and pulled out several before deciding on this one. I think Tyler did well! I love this simple, black crop top and the flannel kept me warm for the walk there and back. I took it off at the venue and tied it around my waist. Overall, 10/10 for this look, I think!
We spent all of Saturday walking around Chicago. We did the Sky Deck on the Willis Tower, stopped by the bean, and just explored the city. It was fun and consisted of lots of walking. He picked out a comfy sweater and jeans, but I had my coat on the entire day, so I figured I’d take a photo of the “going out” look he put together. After walking about 8 miles throughout the course of the day, we headed for the hotel and arrived about 8pm. We relaxed for a bit and leisurely got ready. We found out that Tyler doesn’t know much about skirts, which I would expect. He asked what were considered more dressy skirts, so I showed him what I considered dressy or what was flexible and could be dressed up or down. He settled on this maroon and black high-waisted skirt. He then picked out a plain black, 3/4 sleeved dress that I said I could layer that skirt over if he wanted. He liked this option for the added warmth option. Then he said the fleece-lined, black tights would be good, too. While we were out shopping that day, he helped me pick out a necklace and earrings at Forever 21 to spruce it up a bit. Loved this one!
Tyler did pick out Sunday’s outfit, too, but in our IKEA shopping adventure, I forgot to photograph it. It was a easy and comfortable jean + thermal top combo. Nothing too fancy, which was fine after a week of picking out my wardrobe for him and a jam-packed weekend in Chicago for me. Comfy and easy sounded fantastic. I thought this whole challenge was fun and Tyler got a kick out of it, too. I think if we did it again, I’d maybe encourage him to choose something he thought was “fashionable” or some sort of objective for the day instead of just whatever he wanted. I mentioned doing the makeup challenge at some point in the future and he said he’d try, but I don’t think we’ll have as amazing results as we did this time… Until next time!