I let my Hawaiian-shirt-wearing fiancé choose my outfits for a week.


Editor’s note: To start the new year, CharlotteFive writers and staffers committed to 7-day, 14-day and 30-day challenges through January to shake up our norms and lifestyles. Other challenges included the Minimalist Game, 14 days of veganism, 14 days of talking to strangers, 7 days of classic Charlotte things, and Whole30.

I’ve resolved to stop sweating the small stuff (and to be less like Monica from Friends) in the New Year. That resolution extended itself into a challenge: allow my fiancé, Andrew, to dress me for a full week. 

Fine, I’ll admit it: I’m kind of a control freak.

If you ask Andrew, my co-workers, my close friends or pretty much anyone I know, they’ll tell you I’m a bit obsessive compulsive — particularly when it comes to aesthetics.

This detail-oriented obsessiveness extends to things like my cubicle or our living room,  where all visible items are organized evenly in a straight line — as well as my closet, where my clothes are organized first by color, then by sleeve length.

It also extends to my outfits themselves. I wouldn’t call myself particularly fashionable, but I know what I like. Most of my clothes are neutral in color, and I know which items I prefer to pair together. I tend to wear the same outfits in a cycle, because I know what matches and what I feel good in. Boring? Yes. Comfortable? Also yes.

First, we set a few ground rules.

So, the idea was that I’d give up control and allow Andrew to style me for a week, wearing whatever clothing and accessories he chose for a full seven days. I couldn’t reject any of his choices.

He agreed not to choose any of the “default outfits” he’d seen me wear over the course of our five years together, but he also promised not to make me look intentionally ridiculous (although he did eye my Halloween costumes wistfully before making that promise).

I hoped to come out the other side of this challenge a little more relaxed, and obsessing a little less over what I wore and how I presented myself to the world.

His first question: “Do you own a vest?”

I was screwed.

Shockingly, there was a method to his madness.

It’s worth noting that Andrew is best-known by his co-workers and friends as someone who has willingly grown a man-bun and has worn Hawaiian shirts every Friday since he’s entered the work force. So you can imagine how concerned I was about his wardrobe choices.

We began this challenge on the first day back to work after the holidays, which happened to be a four-day work week. So, Andrew picked all four of my work-week outfits out on New Year’s Day.

As he dug through my closet, he picked four items around which he’d base each ensemble. The first was the only vest I own, a drapey taupe sweater vest with thick black stripes at the bottom. The second was a bright orange kimono. The third was a pair of maroon pants. And the fourth was an Alex and Ani bracelet with my birthstone, an emerald.

Starting with each of these items as the foundation, he was able to build up the rest of the outfit to go with the vibe he was aiming for.

“All of your clothes are pretty simple,” Andrew noted. “There aren’t enough different colors and textures to pair together. I like how you dress normally, but I want to find some different stuff that you haven’t worn in a while.”

Let the games begin.

Outfit 1: Stripes on stripes.

The outfit: 

  • A black sweater with thin taupe stripes
  • A taupe sweater vest with thick black stripes
  • Black jeans
  • Cognac boots
  • Cognac crossbody bag
  • Gold moon necklace
  • Black stud earrings

His reasoning: 

Andrew chose the vest first, then he chose the sweater beneath it because it had the same colors in it. He didn’t really think about the stripes; he just cared that the colors matched. Same with the boots and purse, which he added because “there wouldn’t be any color otherwise.” He chose the moon necklace to remind me of our dog, Luna.

The reaction: 

I usually wouldn’t pair two types of stripes in the same outfit, but it weirdly kind of worked with this one. I liked that the whole outfit was made up of neutrals, because that’s my usual. It was also warm and cozy, ideal for the frigid weather.

This felt like he was easing me into the week, which I appreciated. My co-worker Caroline told me I looked chic, so I counted this one as a win.

Outfit 2: Lots of statements.

The outfit:

  • A bright orange, paisley-patterned kimono
  • A white cotton tank top
  • Blue jeans
  • Flat grey boots
  • A navy statement necklace
  • Bronze feather drop earrings

His reasoning: 

He started with the kimono. Since it’s bright and it has a lot of patterns, he chose a plain white tank top for underneath it, a pair of dark blue jeans, and simple boots that would blend in with the jeans so the kimono could stand out. He also thought the dark necklace contrasted with the bright pattern of the kimono — plus, it matched the jeans. The earrings just seemed hippie-ish, so he paired them with the also hippie-ish kimono.

The reaction: 

I hadn’t worn this (very thin) kimono since summer, because it didn’t offer any warmth — so I wasn’t thrilled to wear it on a 20-degree winter day. I also usually let one item be the focal point of an outfit, so wearing a statement necklace and drop earrings with the kimono felt like overload to me. I usually pair a dressy item like this kimono with a heeled boot, so the flat boots made me feel sort of like I was about to go exploring.

My co-workers, however, had no complaints. They thought this ensemble looked fun.

Outfit 3: Color rush day.

The outfit: 

  • Maroon pants
  • A maroon shirt with thick mauve stripes and thin multicolored stripes
  • A mauve cardigan
  • Taupe boots
  • Maroon and mauve drop earrings

His reasoning: 

“You know how the NFL does color rush?” Andrew asked. (Full disclosure, I did not. But Wikipedia told me it’s when two teams wear matchup-specific uniforms that are primarily one solid color with alternating colored accents.) “This outfit is like that. The color is maroon.”

The reaction: 

I honestly laughed out loud at this. Maroon on maroon? Was he joking? But for some reason, no one at work saw any issue with this. In fact, they thought the whole thing just kind of went together. And of course, my male co-worker Tyler was particularly appreciative of the NFL roots behind the wardrobe choice.

Outfit 4: Army-inspired.

The outfit: 

  • Army green pants
  • Black combat boots
  • A black blouse with a white and kelly green floral pattern
  • A black cardigan
  • A silver Alex and Ani bracelet featuring my birthstone, an emerald
  • A silver geometric necklace

His reasoning: 

It started with the Alex and Ani bracelet. “You haven’t worn this in a while,” he noted, placing it on the bed, the emerald stone glittering. He pulled out a pair of army green pants (to match the emerald, apparently), then paired them with a pair of black combat boots “because that’s what army people wear.”

He pulled out the black shirt with the pattern because it also had green in it, then a black cardigan to “tie it all together.” The silver necklace was because the bracelet was also silver.

The reaction: 

This was my least favorite outfit. I don’t love wearing those combat boots unless it’s with a pair of black leggings, because they make my legs look even shorter. The green in the shirt and the bracelet was a different green from the pants. The masculine “Go Army” vibe on the bottom didn’t go with the floral, feminine feel on top.

But my co-workers rolled their eyes at these complaints, saying the whole thing looked fine (though they did laugh at it all starting with the bracelet).

Outfit 5: Farmer Alicia.

The outfit: 

  • A flannel shirt
  • Blue jeans
  • A pair of (very worn) brown combat boots

His reasoning: 

“You’ll be comfortable, and it all goes together.” Yup. That’s it on this one.

The reaction: 

Listen, I’m all about comfort. I usually wear this flannel, open and with a white v-neck under it, paired with the same jeans and my white Chucks, out to breweries in our neighborhood. But when you button the flannel up and pair it with what look like literal working boots, the effect is very “home on the range.”

Top that off with the fact that Andrew was picking out an outfit for me to wear to a work party (to which I’d usually wear something nicer like black jeans, black heeled boots and some sort of blouse) and I was not particularly pleased.

My co-workers (who were dressed like normal people at a party, in outfits like the one I described parenthetically above) thought this outfit looked fine. Are you noticing a pattern? I think they were just impressed that Andrew hadn’t put me in a Hawaiian shirt yet.

Outfit 6: Cozy neutrals.

The outfit: 

  • Black jeans
  • A marled grey-and-black sweater
  • A white, black and grey blanket scarf
  • A black beanie
  • Grey boots

His reasoning: 

We were heading to a bonfire at a friend’s, and he wanted to make sure I was warm. I think he also knew I was missing my beloved neutral colors by this point in the week.

The reaction: 

No one seemed to notice that I hadn’t dressed myself, which I took as a positive thing. I liked that the greys and blacks all went together, plus I’m a sucker for a blanket scarf. And I was very warm at the bonfire.

Outfit 7: Flowy, with an edge.

The outfit: 

  • A pinkish-tan, open-front, flowy cardigan
  • An sleeveless, ivory, chiffon blouse
  • Blue jeans
  • Cognag boots
  • Pinkish-tan stud earrings
  • A bronze, layered, geometric necklace

His reasoning: 

This was another color outfit. He started with the pinkish-tan cardigan and decided to keep that the main focus of the outfit, while keeping the rest of the pieces in the same warm color family (aside from the jeans).

The reaction: 

This was probably my favorite outfit of the week. These neutral colors were right in my wheelhouse, and this is one of my favorite necklaces — but I never would have thought to pair it (or the casual cardigan) with this somewhat business-y blouse. My co-workers saw it and actually thought I was back to dressing myself, which again, I counted as a win.

I left this challenge with a few main takeaways.

First and foremost: this could’ve been a lot worse. I’m grateful that Andrew actually put thought (and a weird amount of logic) into planning these outfits, and tried to choose what he thought would look best.

I also learned that (I’ll go ahead and generalize here) men seem to care a lot more about colors than any other part of the outfit selection process. They want the purse and the shoes and the accessories all to match precisely. The rest seems to be secondary.

Andrew obviously wasn’t looking at the components of these ensembles and reflecting on past experiences wearing them. Of course he couldn’t be like, “Oh, that’s that shirt I only wear with a very specific sweater because otherwise it makes my hips look wide.” I actually wore a few things I had written off as not flattering to my figure, and I ended up not hating it. Now, those items get a second chance.

The big thing I learned, though, is that other people don’t really care what I wear. No one batted an eye at any of these wardrobe choices, not even the ones that I considered heinous. Once I went back to dressing myself the following week, no one made  comments indicating any kind of big difference between Andrew’s choices and my own.

It seems that all of that effort I put into making sure every part of my outfits match isn’t doing anything for anyone other than me.

But you know what? That’s the main thing I learned.

I guess don’t really care how other people think I look, I care how think I look. I care if feel confident and comfortable in an outfit, not if other people think I look good in it or not. And I think that finding what I feel confident and happy wearing is a good enough reason to be particular in my wardrobe choices.

So, if you’ll excuse me, I’ve got some meticulously matched outfits to pick out.


  1. This had a surprisingly deep ending that I can associate well with. Also, guy here who has a hard time getting past the color-matching thing. lol cant help it. (ps: neutrals are the best)


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