Any woman who’s ever wondered what to wear knows that styling can be trickier than it looks. You have to consider where you’re going, what it’s like outside, what you’re in the mood to wear, what’s clean, what matches, and what fits. It’s why it can take me a ridiculously long time to pick a relatively basic outfit.
My live-in fiancé David doesn’t get it. And because he’s the kind of guy who’s long worn a uniform — a plaid button-down and a hoodie with skinny jeans and Vans sneakers — he isn’t much help when I ask (on the regular): “Ugh, what should I wear?”
Because David’s always been pretty vocal about the kind of women’s clothes he hates (i.e., my animal print romper, anything sparkly) and complimentary when I wear something he likes, I thought he might have some fashion chops if he were put on the spot. So I challenged him to dress me for seven days straight. In the best-case scenario, I thought, he’d pick my sexiest, most flattering clothes, so I’d look awesome all week and confirm which clothes look best on me. At the very least, I imagined, his help would save me a few minutes in the morning and relieve me of the stress I sometimes feel when getting dressed — particularly when I’m rushing off to work and up against an admittedly disorganized closet.
Because David could not give less of a shit about fashion, I was pretty floored when he agreed to style me — no questions asked. “Great,” he said. “You’re going to look like a Bushwick architect!” While his comment simultaneously confused and terrified me, I was excited to see what he’d pick out. Here’s what I ended up wearing:
Day 1: Chambray Dress With Khaki Jacket and Tan Slip-Ons
David says: When I first went into the closet, I caused a few avalanches. Every time I would grab a something from a stack, 10 things above it would fall down on me. I was ready to quit on the spot. So I wouldn’t have to deal with finding a matching top and bottom, I settled on a dress. I know I took the easy way out, but I had to get my feet wet. I felt like the colors in the dress and jacket worked. I considered a few different necklaces, but ultimately skipped them. I don’t change my wallet to go with different outfits, so it didn’t cross my mind to pick a bag.
My take: This was an outfit I probably would have picked out myself — I mean, David may have even seen me wear it a few times before. But the baby doll silhouette, in my opinion, is the opposite of sexy — and I didn’t even know David liked this dress.
Day 2: Black Pants With Light Denim Shirt, Black Cutout Oxford Shoes, and Three Bangle Bracelets
David says: I love these black shoes so I decided to plan the outfit from the bottom up. I got pretty frustrated trying to figure out what matched with them and just wanted to get the shoes on and be done with it. I think the shirt looked good and I liked the outfit. I like when women wears things that are less restrictive and flowy — it sends a relaxed vibe that says, “I’m chill and laid back,” which makes me feel comfortable. I also found some bracelets that looked good together. I guess I’m a bangles man.
My take: I was actually glad that David put me in these shoes because I’d bought them a few weeks ago and was still kind of unsure of whether I liked them and how to style them. He didn’t do so badly.
That said, I stopped wearing the pants he picked two seasons ago because they’re a weird material and have an awkwardly low waistband. I actually meant to throw out the shirt because it has a subtle-but-still-present permanent mustard stain on the front. (Just goes to show I shouldn’t keep garbage in my closet.)
I really wasn’t into the bracelets: David picked three random, I-really-shouldn’t-waste-jewelry-box-space-on-these-nor-wear-them-together bangles. They clinked around on my wrist all day and generally annoyed the shit out of me.
What made me most uncomfortable was going out in this outfit after work. I went straight to a chic rooftop press party full of well-dressed A-listers. I looked just glamorous enough to make a name for myself finger painting. I felt super out of place and stupidly enjoyed myself less because of it.
Day 3: Gray Skinny Jeans, Black Printed Tank Top, Leather Jacket With Short Boots and Gold Cuff
David says: I had a lot of trouble anticipating what different clothes combinations would look like on. With this outfit, I was going for Brooklyn hipster, but I think missed it by a few decades because it ended up looking more like ’80s punk rock. If I could do this outfit over, I’d do darker pants because they felt too light against the boots. I picked the gold bracelet because I really like it.
My take: I wasn’t surprised that David gravitated toward my beat-up boots because he compliments me every time I wear them. But I really can’t tell you why he paired them with an old graphic tee he found in my pajama drawer. (FWIW I do own lots and lots of other shirts.) I would have chosen to wear the leather jacket or boots, and pair it with something more feminine to balance everything out. Oh well!
Still, I thought it was cute that he paired the whole getup with that bracelet — it was an anniversary gift from him. That said, it could have been a passive-aggressive pick because I don’t wear the bracelet very often. (I definitely wouldn’t have worn it with this outfit.)
Luckily Cosmo‘s office dress code is pretty liberal, so no one blinked twice when I came to work looking like I’d just joined a biker gang. I didn’t hate the outfit, but I couldn’t feel father from chic, professional, or sexy, which didn’t exactly stoke my confidence for the day.
And of course the biggest problem was that David didn’t account for the weather when dressed me, so I was stuck sweating through thick jeans and leather in 75-degree weather with a humidity that felt like about 100 percent.
Day 4: Dress, Printed Cardigan With Knit Belt, Hooded Jacket With Tie Waist, Skull-Print Canvas Slip-Ons, Silver and Turquoise Cuff
David says: I picked this dress because I wanted to try something fancier than the first three days, but then I realized it was cold and raining and probably not dress weather. I didn’t want to start over, so I looked out the window to see what other people were wearing and went back to the closet for what looked like a rain jacket. The thin fabric didn’t seem like it would be warm enough, so I also picked out the sweater. The colors seemed to work well with the colors on the dress. I thought this looked good except that there are a lot of straps going on — in retrospect, I don’t know if I should have put them all together.
Choosing shoes was the hardest part. I don’t know how to do heels, so I picked a pair of black and white shoes without heels to match the colors in the dress. I was all about the bracelet I found — I never saw it before but I really like the color. It’s my style.
My take: I wear lots of dresses because they’re typically effortless — all you really need to add is shoes and you’re out the door. So I don’t know how or why David started with a perfectly nice dress and sent me out the door looking like a confused Nordic-rain goddess with two waist-cinching belts and mismatched prints (the shoes and the sweater).
To David’s credit, the colors of the shoes, dress, and sweater were pretty similar, and my upper body was pretty toasty on the bitter cold day. But the only time I’d wear this combo would be on an emergency trip from my office to a ski lodge in the rain — assuming all my other shoes had somehow been incinerated and it was dark enough for no one to see me. The rain soaked through my canvas shoes before I got off my block, and they left me way underdressed at another fancy event after work. I really should have been wearing heels.
The bracelet was a particularly interesting choice because I know for a fact that David had never seen it before — I stopped wearing it when I broke up with the ex-boyfriend who gave it to me. For that reason, the silver was all tarnished. I didn’t have silver cleaner on hand so I had to wear the bracelet in all its tarnished glory.
Day 5: Black Jeans, Plaid Collared Shirt, Striped Wool Sweater, Khaki Jacket, Converse Sneakers
David says: Even though picking out clothes for the weekend felt easier than choosing things for weekdays, after four days of styling I was over this whole thing. I picked the plaid shirt first because plaid is pretty much the only print I wear, and menswear and women’s wear can sort of overlap on weekends. It was cold out so I tried to find a round-neck sweater — I think that goes best with collars. I knew the striped sweater and the plaid didn’t go together, but the colors sort of worked and I didn’t want to go back to square one so I just tucked the collar into the shirt. It was kind of an act of defiance because I know you’re not supposed to do that, but I still liked the look. I didn’t pick any jewelry because it’s a weekend and there’s no need to bother with jewelry on weekends.
My take: I actually don’t really mind mixing plaid and stripes — except in this situation, which involved a lot of colors. Unsure of the print-on-print, David insisted I tuck the shirt collar into the sweater, which made me look like even more of a mess.
I liked that David threw the jacket in there — turns out he’s actually pretty good at layering! And to his credit, I was comfortable and warm enough to wander around the city all day without complaint. He picked comfortable shoes so the outfit was very practical, albeit a little frumpy.
Day 6: Leggings, White Tank Top, Plaid Button-Down, Long Hoodie, Leather Jacket, and Metallic Slip-On Sneakers
David says: I picked out another plaid shirt but wanted the outfit to be warm enough, so I added a hoodie. I didn’t realize the sweatshirt would be so long and create this illusion of wearing a trench coat. I picked out leggings because that’s what girls wear on weekends, even though I don’t fully understand between the difference between tights and leggings besides the fact that one has feet. I usually don’t like these shoes because they’re a little too sparkly for me, but they worked out against all the dark going on here. This seems like the most comfortable outfit of the week, which I’m all about.
My take: Because I was wearing so many long-sleeved layers underneath a fairly slim-cut jacket, I could barely bend my elbows all day — it was really the worst. You can’t see it from the photo, but the base layer of this outfit was sleeveless tank with open sides (a tank I’d typically wear with a sports bra at the gym). Because I wasn’t going to the gym, I wore a regular bra. But it wasn’t until I got overheated and removed a few layers that David realized he’d put me in this awkward tee with massive armholes that basically exposed both boobs. (He didn’t seem to mind.)
Besides the fact that I usually save these sweat-wicking leggings for the gym, I wasn’t opposed to this outfit — even though David and I basically matched. It was becoming clear he was giving up on women’s clothing and just dressing me like himself. It’s cute, but disconcerting — I mean, he could have just as easily dressed me in the all-time skimpiest outfit. I wondered why he kept gravitating toward my most rugged and least feminine clothing, going out of his way to cover me up.
Day 7: Floral Tee With Skirt, Chunky Cardigan, Leather Jacket, Black Tights, and Metallic Slip-On Sneakers
David says: For the last day of this challenge, I thought I’d get more experimental and playful by picking a patterned shirt and a skirt. Except I realized that I had no idea how the skirt worked and what to do with the shirt — tuck it in? Tuck it out? I still don’t really know. I don’t think the whole black-sweater-under-the-jacket thing worked — I don’t know what’s going on there, I just didn’t want the outfit to be too cold. I think I finally figured out the difference between leggings and tights, so that’s good.
My take: I could tell that David was so over it because he picked a shirt that he’s straight-up told me he hates. He was clearly getting desperate/giving up on creating outfits he actually wanted to see me in. It was pretty funny to see David try to style the shirt and skirt combo. It’s like he was born with the fundamental inability to visualize what different clothes silhouettes look like. It must be a guy thing. I felt super frumpy in this outfit, which really turned me off from every clothing item I was wearing and made me feel immeasurably relieved to reach the tail end of the challenge.
David: Fashion is not my thing. Picking out outfits was fun at first, but ended up stressing me out, especially when I had to pick out outfits before work. It’s probably easier when you’re not racing against the clock. I have more sympathy now — I get why women get frustrated by figuring out to wear. But now I know Liz is lying when she says she has nothing to wear. She has plenty.
Me: Even though David didn’t really take to picking out my outfits, it was an enormous relief — hell, a luxury — to have someone else style me for a change. Still, I was a little disappointed that David didn’t show me the stylish light or seriously shake up my look. On most days of the week, I might as well have picked out my own outfits because I felt just like myself (or like a frumpier, less stylish version of me).
But I lived. And if I learned anything, it’s that it’s silly to stress over what you wear because being a little bit underdressed or uncomfortable isn’t exactly a life-threatening situation. (It’s only clothes!)
The biggest surprise of all was that David didn’t put me in one conventionally sexy outfit. (When I asked him why, he argued that he had — and that we disagree about what looks sexy. He said I looked sexy — to him — all week.)
In hindsight, I’m pretty freaking lucky that David didn’t totally try to dress me like someone I’m not. The poor guy just tried to make me feel comfortable and I can’t help but appreciate that.