I Let My Boyfriend Dress Me for a Week
11.28.17

I can name a number of fun stress tests for your romantic relationship.

You two can go to IKEA to test your emotional endurance. You guys can get lost while driving in a city with lots of one-way streets and restrictions on turns to test your conflict resolution skills. One of you can get food poisoning while the other has a cold to test compassion. To test trust, you can ask your partner to dress you for a week.

I asked mine to dress me for the sake of a story. I was trying to find a casual, low-key way to let the world know I had a boyfriend and this seemed the obvious solution. What I thought I’d get were six days of meta-vicarious dressing: that he’d put me in a combination of the wackier, more fun “fashion” stuff I tend to relegate to the back and side corners of my closet until an opportunity permits and the sexier stuff I don’t always have the guts to wear, because where am I even trying to go?

Seven years in this industry has led me to accrue some real star-spangled snazzers, but I rarely wear them. I’m too practical. I hate to be uncomfortable, overdressed, overheated or cold. I have a strong, deep-rooted equestrian aesthetic that keeps me on the straight and narrow. Embracing it feels like home, but part of why I find styling stories for Man Repeller cathartic is because I can dress all the other personalities in my head. I can be so boring when it comes to my own clothes.

Looking into someone else’s closet has the same appeal of eyeing your partner’s meal. It’s magically more appetizing than your own. I hoped my boyfriend would open my closet doors to reveal all the things I secretly want to wear at once and go, “Holy shit! There is giant yellow faux-fur coat and a pair of red cowboy boots in here! Hand me a pair of underwear! Bingo!”

I prayed for it.

Instead, it turns out that my boyfriend, who I am not at liberty to name (he’s not a celebrity or Voldemort, he’s just not “an internet person”), has impressive taste. Halfway through, Leandra said she preferred his style to mine. All outfits he crafted were appraised by various fashion industry friends. It was an event-and-meeting heavy week; his looks got a lot of face time. I’d call the overwhelming majority of response “aggressively positive,” and when I asked each person what it was they liked, many noted his attention to color-coordinating. Straight men, I’ll go out on a limb and generalize, have internalized that shoes must match belt must match watch — and I think that kind of put-together intentionality is really having a “thing” in fashion post-90s grunge redux, which the public responded to.

The process itself was like a sartorial trust fall. I had no idea how scary it was to hand the keys to your wardrobe over to someone else and couldn’t predict how vulnerable it would make me feel. A person’s individual organizational system is a very private thing! More than that, I had to trust he’d pick something wearable, work-in-able, professional, that I liked, that I felt comfortable in, secret hopes aside. We agreed I would tell him my day’s schedule, but that I couldn’t chime in otherwise unless he asked for help. “Do you have [insert kind of item here]?” was the only question he asked throughout. (According to him, I am missing a red suede skirt in a very specific shape — sort of like an A-line tube, if that’s possible.)

Meanwhile, he had to trust that I’d wear what he picked out. Most mornings I wasn’t there for his creative process. He worked without supervision while I was at the gym and laid the outfits out (!!!!! I know !!!!) on my bed, accessories and all.

Of all the outfits he put together — my approval rating of his week’s worth of styling an ascending line from first look to final — I loved the last outfit the most. It was designated for my family’s Thanksgiving dinner with consideration for stuffing consumption, so note that extra points were awarded. The Diamonds are a casual dining bunch, no festive attire required to attend the table. I take advantage of this rule often by showing up to holiday meals in not-the-cool-kind of athleisure. On this day, however, I surprised everyone by wearing a plaid ankle-length skirt and an open-back navy turtleneck with kitten heels thanks to my nameless partner. Can you imagine? It brought the house down. I felt like the favorite child; he got the people’s choice award.

What I learned is that my boyfriend knows me well. Some of these outfits were reminiscent of things I’ve worn before, but tidier, more coordinated, more formal iterations with accessories I likely wouldn’t have picked out. His choices made me realize just how much of a crutch jeans are for me, and how nice it was to try something new. It also never fails to shock me how differently people respond when you wear heels versus flats, as though it’s a sign you mean business. Per him, in addition to not owning enough “pants-pants,” I have abused leopard, could use more color, should not worry about what day of the week it is when it comes to dressing up and could stand to think more about how to “match” my clothes to my hair.

No arguments. Which is surprising, I guess, but it means the relationship stress test worked. Onward, then! To IKEA we go.

Get more Fashion ?
  • Lauren Caudle

    You’re a brave soul, Amelia!

  • Bmo

    these are so good???

    I have a lot of calf/ankle length skirts that I love but can’t seem to make myself wear. It doesn’t help that my office is SUPER casual (like there are people walking around with no shoes).

    • Bmo

      That get’s me thinking! I don’t know if you guys have done this before, but an article about how to feel okay with dressing up/cool when everyone else is in cargo shorts would be amazing.

      • Whitney

        I second this

      • Amelia Diamond

        okay!! like how to feel okay.. EMOTIONALLY.. or a style post [with a literal dressing how-to?] or a combo? also know you guys want to see a style story about “what the fuck do i wear at an actually corporate office where you can’t wear your bra outside your suit jacket for pizazz”)

        • Bmo

          For me it’s definitely more of an emotional problem. I could wear literally ANYTHING to my office but it’s hard to get past jeans/leggings when everyone else is super casual. I think this would also apply to college students who are looking to dress cooler while surrounded by people in hoodies. Any combo of what you mentioned is good, too!

          Thanks!! 🙂

          • Amelia Diamond

            ok!!

          • Amelia Diamond
          • Olivia Black

            This would be so great! !hard not to feel silly dressing up in college when everyone else is in yoga pants !! (no hate to yoga pants, I just wanna go all out some days and not feel silly!!)

        • CarlyC

          Please do this! I work in a medical office and my options are very limited as to what I can wear.
          My restrictions are reasonable given the circumstances (no jeans/leggings, no short-anything, must be wearing sensible shoes, must be wearing some type of blue/black/gray cardigan or sweater) but because work takes up most of my time,whenever I have additional funds for clothes I have to think pragmatically and less creatively which I think is taking a toll on my personal style because I can only really justify purchasing things that are also wearable to work. HELP!

          • Kristin

            are these personally established restrictions or does your dress code actually use the word “sensible” and impose cardigans?

          • CarlyC

            Established restrictions. Our “uniform” (as someone working in the front office) is considered business casual and does require us to wear some type blazer, sweater, or cardigan.

          • Kristin

            That is such an intense dress code! Part of me feels like you should hire a lawyer—Dr Mindy Kaling did not limit herself to blue black and grey and nor should you have to. And what if it is not sweater weather?
            I guess there can still be textures and embellishments …but sounds pretty restrictive, good luck !

          • Kiks

            See my comment above — Dr Mindy Lahiri’s style is my biggest inspiration at work!

          • CarlyC

            Well I know what show I’m binging next. 🙂

          • Kristin

            Would love a pic. I wear so many secrets under my labcoat and it is kind of the best worst thing. But i can’t believe that an office dress code can be so specific and strict . It feels unamerican.

          • Kiks

            I guess you can’t trust people to know what’s acceptable for workwear.

            The last pharmacy I worked in, we had co-op students who showed up for placement literally wearing leggings-as-pants and a crop top.

            At my current job we had a short-lived assistant who came in every morning with her (nearly waist-length) hair soaking wet and flying all over everything.

            Actually at my job they also have rules about what sort of shoes the assistants are allowed to wear (sneakers cannot be “bright colours”???) and only solid-coloured sweaters can be worn over scrubs. No patterns.

          • rachel

            I work at a bank so I have similar requirements, with the added restriction that I can’t wear bright colors or most patterns since I have to be on video. Something like this would be a huge help for me as well!

          • Kiks

            I am a pharmacist and wear a lab coat every day. I’ve felt similarly restricted because I LOVE weird and dramatic shapes — super full skirts, asymmetrical hemlines, giant sleeves, ruffled shoulders. Obviously none of these things works under a lab coat. For a while I just bought super basic shift dresses and pencil skirts, and it was so boring. Plus I really can’t afford to have two completely distinct wardrobes.

            Lately I have been into metallic or pleated (or both) midi skirts (I have one from Anthro that’s turquoise and shiny, it looks like a mermaid); Victorian-inspired high necklines; super bright coloured blouses; and semi-sheer thin knit tops that I wear with a nude bodysuit underneath.
            After six years of this profession, I’ve finally gotten to the point where I still feel like my fab self at work, and my kicky outfits always get compliments from both colleagues and patients. 🙂

          • CarlyC

            I took a screen shot of this and I’ll definitely be using it as inspiration next time I go shopping. THANK YOU.

          • Kiks

            Yay! I’m glad you found it helpful.

  • Ciccollina

    Wow, he did super well! Once, I couldn’t decide what to wear to a party so I asked my bf to choose something whilst I was in the shower. When I came out he was like “ok, so I picked this top, and this skirt.” My response? “That’s a boob tube*, and so it that.”

    * This was back in the day when boob tubes were a real thing.

    • Amelia Diamond

      oh i had a boob tube – from BP if i remember correctly

  • LOLOL I sent this line to about 15 people on my gchat…
    “I asked mine to dress me for the sake of a story. I was trying to find a casual, low-key way to let the world know I had a boyfriend and this seemed the obvious solution” you crack me up gurl. thumbs up to your stylist, i hope to see more of his werk in the future!!! fashion week?! that would be BRAVE.

  • This was fascinating and v enjoyable to read, mostly because the outfits are SO GOOD but also because I’ve seen your bf on instagram stories (that felt creepy to write I’m sorry!?) and he seems like a delightful human.

    Days 2 and 6 are my faaavorites. Never thought I’d like the styling of a Canadian Tuxedo so darn much.

    • Amelia Diamond

      yayy i’m the creepiest love when others join me!!

      • Teresa

        Also semi-creepy, the new apartment looks beautiful. Please give us a “real cool people, real cool apartments” for yourself!!!!

        • Amelia Diamond

          thank you!! i want to – the wall you see is the only finished part so once i finish, I’ll do it. I’m currently trying to get Emily Zirimis to do hers!

    • Adrianna

      I’m here to one up your creepiness – Amelia, your boo’s drawings are impressive!

      • Excellent we are all just creepin on instagram. Party at Amelia’s stories!! (also yes would fully agree w the above statement)

      • Amelia Diamond

        i’m gonna read this to him!

  • Charlie

    6 is so good!!

    Also, quickly wanted to say that your father’s jingle on IG stories was the best thing I’ve seen this entire Thanksgiving! (Really catchy too… my sister caught me humming it a few times haha). And that his enthusiasm for MR and what it stands for was just incredibly nice to see!

    • Amelia Diamond

      omg thank you!!! that was so fun. he is happiest at a piano so that was really fun to film. (it’s stuck in my head too which has fast become a nightmare)

      • Charlie

        “Tell her ManRepeller!” 🎹💃🏻!

  • He did such a fantastic job!!

  • I think he excelled! I got my husband to dress me once, he dressed me like Mrs Claus (!), I blogged about it here: http://www.porcelinasworld.com/2015/11/first-snowfall.html

    • Charlie

      ” In the end I appeased him by finding a pair of tights with red seams, but he still seemed quite miffed that my entire legs weren’t going to be bright red. I wasn’t allowed gloves, despite it being only a little above freezing.
      “No pain, no gain!” he declared.
      “You’ve dressed me like Mrs Christmas!” I complained.

      The smile told me that’s what he was going for.”

      Haha! Brilliant

      • You’ll note that the blog post is two years old and I haven’t invited him to repeat the experiment…!

      • Amelia Diamond

        hahah

    • Amelia Diamond

      so funny

  • ValiantlyVarnished

    Your boyfriend has killer style and taste! I would wear every single one of these outfits. And although he wasn’t happy with the burgundy sweater/skirt combo I think it looked really cool.

    • Amelia Diamond

      thank you!! you can borrow them

    • Yes! I loved that one too!

  • tmm16

    Living for Look 4 but also everything? He should really consider freelance styling tbh

  • MAX

    this might be the best story you’ve ever filled. he’s a keeper.

  • Jenna Birch

    “All outfits he crafted were appraised by various fashion industry friends. It was an event-and-meeting heavy week; his looks got a lot of face time. I’d call the overwhelming majority of response ‘aggressively positive,’ and when I asked each person what it was they liked, many noted his attention to color-coordinating. Straight men, I’ll go out on a limb and generalize, have internalized that shoes must match belt must match watch — and I think that kind of put-together intentionality is really having a ‘thing’ in fashion post-90s grunge redux, which the public responded to.”

    Hahaha. This. I love it.

    • Amelia Diamond

      it messed with my mind today because i mixed brown/black and was like oh god… BREAKING THE RULES

      • Jenna Birch

        the shame

    • Adrianna

      My Polish mother coordinates all her accessories. A bag goes with a pair of shoes because they’re the same color

  • meme

    This is great, he’s got good taste! If I did this with my husband I would wear jeans and t-shirts for a week. Think normcore only not in the least cool.

    • Amelia Diamond

      you should try it you never know!!

  • gail.

    Boyfriend did a great job, but I must admit that Day 5 is my favourite with its splash of Amelia’s own styling. I feel like I finally know what to do with the plaid pants that have been tucked in my closet for 2 or 3 years now (fun fact: I don’t own a plain white t-shirt).

    Also… how have I gone my whole life without a plaid maxi skirt!?

    • EmUhLee

      I highly recommend a plaid maxi skirt. You’ll wear it way more often than you think.

  • Caroline Christianson

    Wow this guy is TALENTED and I find it really sweet that he took the project seriously. I asked my bf to dress me on his birthday just because I think it’s fun and funny, but now I may earnestly ask him to step in when I have no inspo (and hope he does as good of a job!!!!)

    • Amelia Diamond

      this week has been very annoying getting dressed myself!! SHOW ME PICS IF HE DOES YOUR OUTFIT

      • Caroline Christianson

        Ok I will! On his birthday, I also got the “you don’t have many *real pants*” comment btw

        • Aydan

          ha this is so my closet as well!!

  • Lauren Carlson

    I literally got cold sweats when I read the title of this article. I can’t imagine what my boyfriend – a loyalist to J.Crew, Banana Republic, and Brooks Brothers – would select for me! But yours did SO GOOD! I also cracked up over his strong opinions about what items you are missing and your lack of “pants-pants” hahaha. #4 is my favorite, but maybe because I also recently came in possession of a fur coat and now feel inspired to make it work on a Monday versus the gala/ball I was obviously planning to wear it to (but have not yet been invited to) when I made the purchase.

    • LazyLogLady

      I kind of want to get a sense of your boyfriend’s regular style for reference, Amelia! Mine lives in t-shirts and ratty jeans and I THINK I would be horrified if he picked my clothes!

    • Kiks

      I wore a vintage fur coat to my work Christmas party on the weekend and one of my coworkers declared me the Lady Gaga of our company. I was like, “I accept!”

  • Leandra Medine

    inSANE how much better his style is than yours. genuinely mind blowing!

  • Marie-Eve

    LOVE Days 1, 4, 5, 6! I want to try this now!

  • G De Siena

    I was dying to know if Amelia had a boyfriend! Best way to tell the world in my honest opinion. I am sure you guys will pass the IKEA test with flying marks too

  • I love how he provided analysis, comments, suggestions an such, not just pick something at random. I definitely have to try this with my boyfriend once I get past this thesis time (athleisure and robes with a side of golden slippers and clip-on earrings).

  • Georgia

    oooOoOoo please make this a series and have all MR significant others do this !!!!

  • Harling Ross

    rly need a visual on what an a-line tube looks like if he can kindly provide thank you so much!!!!

    • ashley

      also really wondering amelia if he wanted to pair the red skirt you didn’t own with the burgundy sweater because that’d be fire

      • Kiks

        That’s what I was thinking too!!

        • Amelia Diamond

          he brought it up a few times!! i have no clue?!

          • Kiks

            I guess you know what you’re getting for Christmas!

    • Like a pencil skirt??

  • me

    OMG DOES BOYFRIEND HAVE A BROTHER ????!?

    please advise because i need a bro with this kind of amazing fashion sense ASAP

  • katemcpsf

    Listen i loved this story… best 10 mins of my day!

    • Amelia Diamond

      KATE!!

  • katemcpsf

    (i’m a slow reader ok?)

    • Amelia Diamond

      so am i!!

  • starryhye

    Your BF did a great job! I’m really impressed. Wonder how my husband of 11 years would fare????

    • Amelia Diamond

      you should ask!!

  • hearceespeak

    i just asked my fiance to dress me for a week. will report back.

    • hearceespeak

      aaaaand he said “no because you’ll be cuter if you do it”

      • Amelia Diamond

        hahaha come onnn

  • Emily

    Aww this is so cute! During thanksgiving I wore a pair of charcoal gray boyfriend cut chino pants and my bf told me I looked like I worked on a kibbutz

  • Jessa Gibboney

    I have always wanted to let my husband dress me for a week (or two days) to shake up my style. This has given me the final push to allow it to happen! He finally used the word “jumper” correctly yesterday, and now this article, it’s a sign!

    • Amelia Diamond

      do it!!

  • B.

    I need to try this, it looks like a lot of fun. Not sure how or when as I sort of have a uniform for work so I cannot let him get creative without putting my wage at risk, but I’ll figure it out. Maybe on holidays.

    • Amelia Diamond

      do it! “Free dress” dressing!

  • doublecurl

    this is such an intense DTR and I am here for it

    • Amelia Diamond

      oh yea i don’t fuck around

  • Anna Ferrante

    Obsessed with this story!

  • Kseniia Korotaieva

    Not to sound cheesy, but with every look the same thought popped in my head – your wardrobe staples are so amazing! I bet not everyone’s boyfriend could perform as great in a project like this simply because not every girl can build up a wardrobe like that!
    I’ll steal a few ideas for my own:)

    • Amelia Diamond

      they’re yours to steal!

      • Kseniia Korotaieva

        The cute little striped bench and bedding are on the list too since the small bedroom post:)

        • Amelia Diamond

          that bench thing is my favorite thing in the apartment I think get it get it! (Weirdly comfy too, i sit and write on it all day but I straddle it like a horse so that i sit straight)

  • Damn he is a good stylist!! I’ve always wanted to try this with my boyfriend. I’ve noticed he’s pretty strict about rules too and he’ll make comments if I’m wearing mismatched styles (the last time was when I wanted to wear my faux fur coat in October, because he said the winter fabric looked weird with my lighter summer/fall textures).

    • Amelia Diamond

      hahaha!! do it do it!

  • You got a good one, Diamond. Cheers!

    • Amelia Diamond

      i love when people call me by my last name because i never played team sports!! it makes me feel so cool seriously thank you

      • Of course!! Let’s co-captain a MR dodgeball game lol 😀

  • JT

    I have to say, he did a great job!!! 👍🏼👍🏼👍🏼😳

  • Sarah

    Honestly this sounds slightly scary but mostly fun! I’ll have to try this.

  • rachel

    Its funny that no one liked #3, because it and #4 were my favorites! I think a big part of the reason I was digging #3 is that I love that skirt, I have been looking for a skirt in that faux wrap style that isn’t made of stretch jersey for what feels like forever. All were great though, your BF makes a pretty good stylist. Is he free to visit Missouri any time soon to do some work styling for me?

    • Amelia Diamond

      hahah yes let me ask

  • Izabela Lodangco

    I want an apartment tour from Amelia! or does she already have one?

    • Amelia Diamond

      ahhh i’d love to but i’m still “working” on it — i moved in july and finally unpacked in OCTOBER. only had my closet done for a while. you know who needs to do her apt first? EMILY ZIRIMIS.

      • Helen

        I would love to see your apartment tour, Amelia!

  • Charlotte

    This was one of the most entertaining/uplifting things I’ve read. “Straight men, I’ll go out on a limb and generalize, have internalized that shoes must match belt must match watch” – feel this on a deep level. My boyfriend is king of coordination.
    Too much #relatable content – being over dressed for a Monday? Wearing heels like you’re the queen?
    And thanksgiving outfit has injected new life into my outfit prospects even though its Summer in Australia !!

    • Sarah Martin

      I thought this was just my boyfriend! I got him a watch for his birthday and he was upset because it didn’t match the leather of his favorite shoes.

  • Kackie Cohen

    Wow, your guy has some style chops. I especially love the Thanksgiving outfit, but all of them are terrific. And such a great couples activity- as you said, a real trust fall!

  • Basil

    I love my husband, but I don’t know if I could trust him to dress me, though he seems fine for me dressing him, which kind of happens by default as he only ever wants work clothes. He tends to basic jeans and t shirts, whereas this is more of my ideal https://instagram.com/p/BcDa55WjzhN/

    • Amelia Diamond

      i love this photo / reference so much

  • Elisabeth Bass

    Amelia, this is precious. I feel like you have the most caring, thoughtful boyfriend, and, while I can’t pick a favorite outfit, I do love the entire process. (You do look like a boss in the fur coat, though.) I read a similar article by a girl who let her grandmother dress her and now I think I may rethink a few of my go-to outfits. Your boyfriend’s comment about matching your hair to the clothes is the cutest thing ever. It never hurts to put your wardrobe on “shuffle.” Hugs.

    • Amelia Diamond

      !!! I can’t wait to read him all of these comments but especially this one! Also I looove the idea of “putting your wardrobe on ‘shuffle’ omg brilliant you and “paradox outfits” above yeesh!

      • Elisabeth Bass

        Thank you! Wardrobe Shuffle could actually be a dice game of sorts if you pre-number the articles of clothing and then “go big or go home” depending on the day. 😂

  • Diana

    uuuuuh on day 4 and day 6 you look glamorous yet made an understatement simultaneously, this are some paradox outfits to die for

    • Amelia Diamond

      i LOVE THE combo word “paradox outfits”!!!!!

  • ashley

    just noticed your riding helmet as shelf decoration – LOVE

    • Amelia Diamond

      that’s from soooo long ago! not regulation! still smells!

  • monochrome

    JEALOUS. Of the boyfriend’s taste, of your amazing wardrobe, of the creativity here. Time to rethink my minimalism – that plaid skirt is amazing.

  • Kattigans

    I freaking loved this! Now i want my bf to dress me just to see what he’d do even though I kind of have an idea. I’m always so surprised and sometimes what he approves when I bring home online shopping items and ask him for a “yay or nay”. Straight men, I tell ya! Some of them are such goodies.

  • “You two can go to IKEA to test your emotional endurance. You guys can get lost while driving in a city with lots of one-way streets and restrictions on turns to test your conflict resolution skills. One of you can get food poisoning while the other has a cold to test compassion.” THIS IS SO TRUE!!! I feel like this is a huge test – and I’m really not sure if my husband could even handle the pressure.

    Also, can we talk about your perfectly styled bookshelf in the background? Care to share the details?

    http://www.shessobright.com

    • Amelia Diamond

      my mom literally “drew out” on paper how to style it because this kind of thing sounds nice to me in theory but stresses me out and I replicated it item for item. sad.

  • dori mondon

    i’m terrified as to what would happen if i did this. i still don’t quite know what my wife’s clothing taste is for femmes (she’s butch).

    • Amelia Diamond

      you two should do it!! more than anything it was so nice not to have to think

  • Pandora Sykes

    hahaha this is so funny – and also so good, love his taste! Wish that Cedric C skirt was myyyyyne

    • Amelia Diamond

      borrow iyt!

  • Owiredua

    “The Diamonds are a casual dining bunch…” with a very glam name! That sentence tickles me LOL

  • Can this be a regular thing? You have got yourselves a keeper! Such cool outfits. In love in 5!

    • Amelia Diamond

      we need to get more team members to do it!

  • Amber

    “According to him, I am missing a red suede skirt in a very specific shape — sort of like an A-line tube.”

    Does he have a brother?

  • I’m kind of jealous that your boyfriend has such great style! Also, that coat is INCREDIBLE.

    • Amelia Diamond

      reformation! get it get it!

  • Dafne Pimentel

    He’s an awesome stylist! Keep him!

  • Susan W

    This story is SO darling! I love his choices and am kind of inspired to ask my husband if he’ll undergo the same challenge with me. He’s an engineer… this could get interesting…