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My Boyfriend Dressed Me For A Week And This Is What Happened

My boyfriend, Chris, doesn’t see me the way I see myself. So I wanted to see how someone who doesn’t have my insecurities would dress me for a week.

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Hey guys, Nina here. I enjoy fashion, but I'm no style queen. When I find something I like and it looks good on me, I stick to it. FOREVER. My daily look is usually a crop top, skirt, gold jewelry, curls, and a jacket.

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I want to diversify my style portfolio. My closet is full of unworn, riskier clothes. But being in a rut means I don't have to confront the things I'm insecure about, like showing my bare arms or wearing bodycon or high-waisted anything. I can hide behind my jackets and black-on-black ensembles.

However, my boyfriend, Chris, doesn't see me the way I see myself. So I wanted to see how someone who doesn't have my insecurities would dress me for a week.

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Chris's Thoughts Pre-Experiment: Nina gravitates towards cute, knee-high dresses. If I had to label her default aesthetic, perhaps I'd call it "girl-next-door chic." The only time she ever wears her hair up is when she's working out, but I think it's a flattering look for her. As far as makeup, I've always been attracted to the "less-is-more" approach. I just want her to have the confidence to capriciously change things up and throw on threads she shied away from in the past.

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1. I'd let Chris choose my outfit, shoes, hairstyle, and makeup for seven days.

2. Chris could buy four to five new items and pair them with existing clothes in my wardrobe.

3. I wouldn't tell anyone I was conducting this experiment, in order to get genuine reactions.

4. I wouldn't reveal how I actually felt about the outfits until the end.

Why Chris picked this outfit: I'd never seen Nina wear a collared shirt, so I took this one off the rack to sate my curiosity. She rarely puts her hair up, too, so I chose a high ponytail both to try something different and not to obscure the collar. Seeing as her ears were no longer covered, earrings felt like a natural addition.

Nina's Day 1 Revelations: I was impressed by this one, very casual chic. I'm not a big button-down shirt fan because my boobs tend to stretch them open, but this one actually worked. Let it be known that Chris told me to cuff my jeans, but I rarely wear pants, so he literally SAT ON THE FLOOR and cuffed them for me, like I was a child. I also never wear my hair up because I think it makes my small head look even more shrunken, but so many people stopped to tell me that it looked cute. Maybe he's on to something.


Why Chris picked this outfit: Nina owns an inordinate number of painfully cute dresses and flats, so I wanted to put her in a combination she seems to prefer yet still pick out a piece I hadn't seen her sport before. To my delight, I discovered this lil' floral number, tucked away amongst other long-forgotten clothes.

Nina's Day 2 Revelations: Chris had me wear silvery-blue eyeshadow to "match" my blue dress and blue flats. UGH. I am VERY insecure about my flabtacular arms, so I envisioned people gawking at my jiggly fat. No one seemed to notice. I felt lost without a jacket to double as a security blanket. This hairstyle really emphasizes how bulbous the lower half of my face is, making me all froggy. One co-worker told me I looked "like a 13-year-old going to church." Lord.

Why Chris picked this oufit: Nina defaults to more demure (and lovely) outfits, so I wanted to try something strident. Lo and behold, a black leather jacket jumped off the hanger, the perfect complement to Nina's spunky side. The hat was a gamble, but I rolled the dice and loved it once I put it on her.

Nina's Day 3 Revelations: OMG THE HAT. I may as well have walked into the office and screamed "I AM WEARING A HAT, WHAT DO WE ALL THINK?!" I felt like a tool, but lots of people went out of their way to tell me they liked it. I usually only wear that necklace with high-cut tops because it literally stabs my cleavage. We also had to google "leather jacket skirt" before Chris would believe that women wore skirts and leather jackets.


Why Chris picked this outfit: I didn't want to detract attention from the scarf, so I supported it with all neutral tones. It appeared that the only pair of sneakers she owned were her running shoes; a trip to the mall rectified that. To top it off, I took the previous day's hat success and let it ride, trying out a beanie.

Nina's Day 4 Revelations: This may be the first time I've ever worn jeans twice in the same week. *Shudder* This outfit just felt very meh. At least the previous outfit tried to make a statement. The beanie also kept sliding off my head, which I took as a sign from the universe that I should not be wearing hats. The only saving grace was my precious cat eyeliner, which I may have gently nudged him toward.

Why Chris picked this outfit: She hardly ever wears pants and certainly never throws on threads like these. So, for the sake of experimentation, I pulled this blast from the past off the rack, fully acknowledging that it would be a polarizing piece. The gold heels jibed nicely with them and harkened back to the days of Studio 54.

Nina's Day 5 Revelations: Oh lord, these pants are the least forgiving thing I've ever worn. It's exactly the reason I stay away from high-waisted shit. They had a tendency to ride up and scream "HERE IS NINA'S VAGINA." Sill, the pants got a ton of compliments. I was shocked. Do people really see me as a boho babe? I'm still not over the pairing of my ultra-fancy heels with these crazy hippie pants. What the hell, Chris.


Why Chris picked this outfit: A fun evening called for something comfortable but with a little flare. I thought this speckled dress, crumpled up in a heap of clothes in the corner of her room, would do the trick, accompanied by some boots.

Nina's Day 6 Revelations: I bought this dress a year ago, and I've put it on at least 10 times and thought, Eh, nah. I'm not this bold person. Wearing it for a night out made me think, What the hell was I so insecure about? It's not a huge departure from how I normally dress, but it was still different. It's just SO MUCH crazy brightness and pattern for a person who thinks a "pop of color" is some navy or gray. But I felt cute, spunky, and ready to take on the night.

Why Chris picked this outfit: I intentionally constructed this ensemble to be the most low-maintenance. I mean, who's gonna get dolled up for the drudgery of errands or the sweet serenity of Netflix and chill? Tee. Shorts. Jacket. Sneakers. Simple. No makeup — no need.

Nina's Day 7 Revelations: Ugh. UGH. I think I love Chris as much as I hate this outfit; so A LOT. The clothes themselves aren't awful together, but it's the styling. He made me try on every flat shoe in my closet and somehow we arrived at my gym sneakers?! WHY?! HOW?! I absolutely detest going outside without at least a little eyeliner, so this was torture. What Chris doesn't understand is that the ~effortless~ look does, in fact, require some effort.


Chris: I was ecstatic with how Wednesday's ensemble turned out. After assembling the punk rock getup, still in the throes of creativity, I looked down at the hat. Was this the missing link? Had I solved this Rubik's Cube of female fashion? I wouldn't go *that* far, but I sure liked it and felt confident that it would turn heads.

Nina: Saturday's outfit was my favorite by a mile. It's probably the closest to my current style, but it pushed me slightly out of my comfort zone. Sure, I'm wearing colors and a zany print, but I still look and feel like "me." Just a slightly more confident, sassy version of me.

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Chris: Sunday's. Would she wear this for anything but a lax day with bae? Fat chance. But she doesn't have to festoon herself with precious metals or toil at the mirror for eons every day to look good. It's my least-favorite outfit, sure, but it's the best fashion accomplishment in that it shows how pretty she is au naturale.

Nina: Fucking Sunday. I look like I've given up. The top half of me is kind of cute, but the bottom is just so sad. My sneakers still have hiking dirt on them. We bought ~fashion~ sneakers for a reason! I honestly think Chris was probably just exhausted. At least we can both agree it kind of sucked.

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Chris: I had an absolute whale of a time. I got to play with all these fun pieces she cast aside or never considered, and that process taught me a ton about fashion. It also instilled in me a newfound appreciation for the effort ladies go through to look and feel great. I think this week Nina sported some pieces that she never would've considered and owned them. She's a beautiful woman who makes even my mess of wardrobe choices look fantastic.

Nina: I've spent years telling myself I "can't" wear certain things. But, after a couple hours of just living my life in those clothes, I forgot that I was supposed to be embarrassed of my arms or my stomach. I also apparently don't hate attention as much as I think I do. I loved it when people complimented my hat or commented on my crazy pants. I can be loud and bold with my fashion choices, and even if they're stupid, the day ends and life moves on. I'm really glad I got to do this experiment with Chris. I should see and treat my body the way he does: like it can wear anything.