What I’d Wear to My Wedding If I Could Have a Do-Over

I got married five years ago in a dress that I found two weeks before my wedding. I was 23 and living at home; the entire ordeal was essentially a party that my parents were throwing for themselves, but at which I would be the guest of honor. I served exactly no purpose throughout the planning process, but graciously elected to find my dress. It was the single responsibility I maintained. Two weeks before the wedding, my mom marched into my room with a thick-ass folder titled “Leandra’s wedding” and asked when she could see the dress. I had an idea of what I wanted: something delicate and light at the top that would explode into layers and layers of tulle around mid-thigh. I wanted to wear a leather jacket over the dress. There would be a flower crown (It was 2012! This was still a novel idea back then!), and so many gold necklaces. Technically, I did not have a dress yet. I told this to my mom, who proceeded to throw her folder at me, papers flying everywhere. “Fine! You deal with your wedding,” she shrieked, which seemed like such a disproportionate reaction to my response, but I recognize that she’d been busting her ass for months to plan this wedding when all I had to do was find a freaking dress, which I didn’t.

Anyway, I’d been writing Man Repeller for two years and had accrued a large enough cohort of friends who were publicists to feel like I’d be okay, even in spite of the time crunch. I emailed someone at Marchesa and asked what they had in a size four. In return, I received exactly two photo options, so I picked one (beggers can’t be choosers!) and bought it over email. There was a bit of tailoring needed, which we did in about 72 hours, and by the time the “big day” came around, I was not naked.

I didn’t look like MY BEST SELF, but who cares/I wasn’t naked. On this: people are always so shocked when I tell them I didn’t like how I looked at my wedding, that I didn’t care so much about the dress and that I just wanted it to be over with (one good indicator that you’re marrying someone you like is when you’re more excited about the binding contract than you are about the binding dress). But it’s the truth. I look at pictures now and roll my eyes, but I’m also grateful that — you know what? I have a story running next week about the six things I wish I knew when I got married, so I’ll just finish that sentence when I get to writing that. Until then, here are four outfits I would wear to my wedding if I were getting married now.

If I were getting married at a hotel in New York City (which is what I did)

What I'd Wear to My Wedding May 2017 Man Repeller1.0 (8 of 51)

Houghton dress, Rachel Comey blazer, Chanel shoes, Laura Lombardi earrings and necklaces

Isn’t this dress something? I know it might seem like I have massacred it with the introduction of a plaid jacket, but I am who I am — a maximalist at best, and someone deeply disinterested in full looks at worst. I also just love the idea of buying things for your wedding that could be easily worn after the fact. This blazer, for example, by Rachel Comey — not cheap by the regular standards of buying stuff just to have, but a complete and utter deal when you’re buying it for your wedding.

If I were getting married at a hotel in New York City (part II)

What I'd Wear to My Wedding May 2017 Man Repeller1.0 (44 of 51)

Rosie Assoulin skirt, Hanro cami, Veda leather jacket, Chanel shoes, Aurélie Bidermann bracelets

This is basically what I did wear, but the products that I selected in real life were not as smart or meditated. Sure, the dress was beautiful, but it also didn’t really fit me. And the jacket? Made from organza with layers of tulle shooting out of it? What the literal fuck was I thinking? If I could do it again, I’d wear Rosie’s comforter of a skirt with a very plain white tank top (this was the real idea back then, but my mother aggressively vetoed it and I guess I didn’t have the agency not to care). For the ceremony, I’d wear a real leather jacket and add fabric bracelets for color. In real life, I wore atrocious platform Superga sneakers. In fake life, I’d prefer black-and-white Chanel mini heels.

If I were getting married on a large sailboat  

What I'd Wear to My Wedding May 2017 Man Repeller1.0 (22 of 51)

Fame and Partners dress, Olivia von Halle robe, Stalvey fanny pack, Aquazzura shoes, Gucci glasses, Jennifer Behr headband, Roxanne Assoulin bracelets

My very own Goldie Hawn circa Overboard moment. Or the artist formerly known as Amelia Diamond. But we would fish! This is why I’m wearing a fanny pack; you never know when you might need to dip into it for bait. The robe is great because it’s extravagant without meaning to be.

If I were getting married in the backyard of a Hampton home among rolling hills and peonies and one long table decorated by tea lights

flying georgia may 2017 man repeller

Viva Aviva skirt, Vita Kin blouse, Foundrae necklaces, Assya bracelet in hair, K.Jaques shoes

This is really what I wanted to do — set up a table for 50 people in the backyard of a summer home in Long Island, where you could smell pine emanating from the trees around you. Yes, it would be literal to pair a big white skirt with a peasant blouse, but who cares? It’s your wedding.

I should really renew my vows.

Special thanks to our model Georgia Hilmer, follow her on Instagram @georgiahilmer. Thank you to Genuine Liquorette for hosting us, follow on Instagram @eatgenuine. Shot by Edith Young, styled by Leandra Medine with market assistance by Elizabeth Tamkin.

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  • meme

    “I just wanted it to be over with (one good indicator that you’re marrying someone you like is when you’re more excited about the binding contract than you are about the binding dress)”. THIS. Maybe it’s because we were also not living together so marriage meant an actually visible change in life, but I just don’t get it when people obsess about the wedding and get sad after it’s over.

  • Ashlee

    I am so with you on this! I got married 4 years ago and, as a last minute choice, wore a simple knee length lace dress from Topshop (also had a flower crown ha). I didn’t love the look but I didn’t really care that much either. If I had a do over I would chose something that reflects more of my personality, probably a jumpsuit!

    • Aydan

      Yessss!! I think jumpsuits are sooo awesome!! I’d probably do it with a crazy yellow satin heel or something!

    • Cristina

      SERIOUSLY. Just read an article on bridal jumpsuits and I was like “I didn’t even know that was a THING” and am so mad about it.

  • Emily

    LOL what an insufferable article. “Well, I couldn’t be bothered to find a dress for the expensive wedding my parents were kind enough to organize, and I didn’t really like the Marchesa gown I wore when I was 23…”

    • I’m not sure if you’re married, but often times a wedding is more about the family than the bride and groom. We wanted to have some modicum of control over ours since we were paying, but it just doesn’t pan out that way because it just means SO MUCH more to your parents than it does to you and you’re like ok whatever.

      • Cristina

        That was definitely one of those LOL’s people use when they are trying to soften being the jerk haha

      • Seriously! I don’t really give a shit about a lot of wedding planning but I’m practically forced to care because my mom/his mom/the venue coordinator ask me a million questions and don’t take “I don’t care, pick what you like” as an answer. At this point I just want to can it and elope, ugh.

        Also, Leandra worked HARD to get MR set up and it would have been ridic to not flex her professional contexts. Hell, I’m doing the same for smaller stuff where I can!

    • mapillski

      um…are you lost?

  • My venue went out of business before my wedding, I had this whole intimate little bar-party envisioned and I would just wear a lace version of what I always wear (cropped tee + a line skirt with pockets+ leather jacket) and there would be balloons and dark corners and bourbon cocktails. Then I got an even better wedding (a garden cocktail party in my in-laws backyard with fall foliage and apple pie!) but ohmygod my wedding-outfit was not a good fit since I was the same color as the tent and blended right into it. I loved my wedding outfit, but I wish I had picked something else when the original venue fell through. Ah well, you can see the relief in my face that the whole thing was over in every single picture of the day if nothing else.

  • Cristina

    Aw man, I was looking forward to a pic of the actual dress!
    I’m with you though. The only reason we even had a small ceremony was because my husband wanted his family there. I could care less. I was just ready to be married and start our lives! And I think it showed in my dress. It wasn’t fun “shopping” for it (gawd, they made me ring a cowboy triangle thing and I wanted TO DIE.). It was flattering, but it wasn’t really me. My hair ended up not cooperating, but surprisingly, the mess that it ended up is me haha. I would love a do-over. Not even a wedding. But a new dress. Maybe for an anniversary, we’ll just re-do our wedding photos!

  • This spoke to me on so many levels. I just got married, and while I loved my dress and it was perfect – I also cringe every time I see a bridal ad on Facebook or get an email from a designer about their new bridal collection – I couldn’t figure out why at first, and then it hit me – I didn’t really like what I looked like at my wedding.
    In the year I was engaged, I had no interest in going to bridal salons to try on a multitude of dresses and be fawned over and drink copious amounts of champagne. I searched online – Reformation, Net-A-Porter, Moda Operandi, J. Crew, Grace Loves Lace, Self-Portrait… I ultimately decided I wanted something affordable and classic, but still a little sexy, so I went with Reformation.
    I think it was a combination of being into this whole non-traditional, Bohemian wedding thing AS WELL AS being really uncomfortable with my weight (I didn’t lose as much as I wanted to), that made me play it safe, and not be true to myself. Yes, I look pretty and my husband couldn’t stop staring and I was oooh-ed and ahhh-ed over, but the whole look wasn’t really me.
    It’s funny, because we came back from the wedding and I chopped off 12″ of my hair, pulled out all of my all-black/neutral toned clothes, and went back to my black eyeliner; I haven’t used any of my shimmery makeup, and I cringe sometimes at some of the wedding photos, especially when I see how big that flower crown was.
    While my wedding was gorgeous and had non-traditional aspects, and was literally one of the best nights of my life (it was small, family only, on the beach, we basically partied and danced all night), I do wish I hadn’t gotten in my head so much about my appearance, and just stayed true to my actual IRL sense of style, and let that translate into my wedding dress/look.

    • “stayed true to my actual IRL sense of style, and let that translate into my wedding dress/look”

      This is SO what I’m trying to do with my upcoming wedding. What’s true to me is something designer that’s off-the-rack. However, what I’m struggling with is that huge pressure to “look like a bride”. While no one says anything, it’s still there. Like, I wonder if guests will be disappointed that my dress is casual and not very bridal, even if I love it myself.

  • Leandra, I am surprised that you didn’t like the way you looked at your wedding! Yes, the outfit looks 2012, but why should it be a bad thing?
    I think it’s the fact that someone reposted that pic that made me discover The Man Repeller for the first time! And I went back several times since 2012 to contemplate this beautiful picture of a happy bride. I think you looked gorgeous and radiant 🙂

    More generally, I try to embrace going with the trends and playing the fashion game: sure, if you don’t follow trends your outfits will never look dated, but then where’s the fun?
    Except for my tattoos, I research my ideas IN DEPTH to make sure I’m not following a trend, but to me tattoos are the opposite of fashion: it’s forever. Maybe that’s the approach that the brides have to the concept of getting married? (I don’t want to get married. I want more tattoos though.)

  • Coralie

    I also got married five years ago and while I did love my dress (Delphine Manivet boho lace etc etc), it was a stupid price and I didn’t feel like it was my favourite thing that I’ve ever worn or anything. A couple of years ago I found a white silk dress from the 30s in a vintage shop in Glasgow for less than $100 and I wish I had got married in that. I just wear it on random days now and people ask me if I’m a runaway bride.

    Btw you looked beautiful at your wedding and I also like the sailboat and Hamptons looks here though I am a city wedding girl all the way

  • Emy M

    Timely for all the spring brides! Why am I only just learning about Fame and Partners now? what a find! My wedding is in 30 days, totally would have worn their Bisette dress !! 🙂

  • Vanessa

    I ❤️ formalwear! I loved your look in 2012 and I love all these looks now.

  • Amber MB

    Please renew your vows every year (at LEAST).

  • AC

    AMAZING first wedding dress, mediocre first husband.
    Mediocre second wedding dress, love of my life second husband.

    • Rheanonn Perez


  • Rheanonn Perez

    i love the first look!!


  • Abby

    I wasn’t bonkers over my wedding dress either. I only went to one store and bought the first decent thing I found in my budget. I’m just not a dress person and in the end I guess I looked fine (my makeup was on point!) but I don’t think I’d pick that dress again.

  • Amy

    The Rosie Assoulin skirt in the link isn’t the one in the picture…. anyone have a link to the one in the photo? I’m into the quilty-looking texture.

  • “the entire ordeal was essentially a party that my parents were throwing for themselves, but at which I would be the guest of honor.”

    YES. this is exactly how i felt. when i think about my wedding, i still feel such a sense of anxiety about all of it–the dress, the venue, the flowers—and because of this, i harbor a little bit of resentment for people who say it was “the most perfect day of their lives.” that said, the day AFTER my wedding really WAS one of the best days of my life. i was so excited to be married to my husband and to begin our life together (still am!), and was so so sooo excited that i was no longer trying to plan a wedding with my mother.

    definitely need to renew those vows and have the late summer in the berkshires dinner party of my dreams.

  • me

    It’s been FIVE YEARS already ?! Damn…. tempus fugit.

    Congrats, sis !

    p.s. your wedding outfit was way better than any of these : )

  • mapillski

    I can’t be in the minority that was in deep love with Leandra’s 2012 wedding look??

    • Nope. I find it the best of them all, too. Much better.

  • Áine Hegarty

    You should renew your vows and wear exactly what you want now! For the record, I thought your wedding garb was really fun.

  • Claire Brockelman

    I just went and looked at your wedding dress, you looked amazing, seriously.

  • Good gosh. Thank you for writing this. I, too, wanted a backyard wedding with twinkling warm lights, a flowing, comfortable dress and about 50 people, but instead I got married in the hottest month of the year in Texas, in a dress I couldn’t sit down in, in front of 350 of our closest friends. I was 25.

    I ended up with that insane discrepancy between what I wanted and what actually happened because I had never dreamed about my wedding day, what I would wear, or what food would be served. I just knew I wanted to marry my now-husband, and that I was committed to our marriage, if not the minutiae of the “big day.” Still, I can’t help but wish I would have done what felt truer to me six years ago, instead of bending to the wills of others.

    I may toss a celebratory vow renewal party in there on some abstract anniversary year to honor the current me (and evolution of the “us” that my husband and I now are), but the fact that “the day” six years ago is what propelled us to where we are now gives me enough grace to honor it (and what I wore) for what it is/was.

  • Claudia Cristina Deveze

    Leandra, there is always vow renewal! Just saying. *wink wink*

  • Kay Nguyen

    Love everything! You look effortlessly beautiful in all of them <3


  • Blythe

    OH MAN this hit close to home for me. My engagement was super quick (about 5 months) and I picked an okay dress, but looking back at photos all I can think now is, “meh”. I have large knockers and went strapless (BIG REGRET). But we look so young and innocent. I want to renew my vows simply to do and wear what I really want. And, I’d look hella different because I have WAY more tattoos than before or as my mother calls it, “the desecration of my beautiful body.”

    Que Bon Jovi’s “It’s My Life”……

  • Harling Ross

    Have clicked through this slideshow no less than 7 times today

    • Olivia AP

      One of the greatest slideshows ever

  • Concerned Mum

    I remember seeing a photo of you and your wonderful wedding dress sometime ago. As someone who had the misfortune to be married in 1986, the worst decade ever for wedding style, I must say you and your dress were so chic. I sent the links to several friends just because I thought it was so fab.

  • Paul Pham

    I remember your dress! I thought it was beautiful, but I had a feeling you were going to regret the jacket looking back. Really felt it should have been leather too.

  • Dale Chong

    these looks are so. me.

  • I’m pretty sure that zebra robe means to be extravagant…. 🙂

  • BDF

    My now husband and I ran away to Rome and got married in front of fifteen of our closest friends. I had a dress & coat made by a dressmaker who makes garments from original vintage patterns and because it was wine-coloured embroidered silk I have worn that coat so much since our wedding! I am so glad we didn’t do anything “traditional” because it just wouldn’t have been us. And our Italian friends tell us we have started a trend for “informal” weddings where the entire wedding party walks together from the wedding, to a bar, to lunch, back to the bar, to another bar…

  • Michelle

    I think most of us would do it a little (or a lot!) differently! My dress was beautiful, but not something I would pick now. It was 2007 and most dresses were strapless. I had a traditional wedding. Really all I cared about was being married to my husband who I just celebrated 10 wonderful years with. I never cared too much about a wedding and just went with what my husband and family wanted. My regret is not having a simpler, back garden style wedding. Alas, there are no real wedding regrets with a happy marriage!

  • Maureen Krezel French

    i loved what you wore the first time. and you couldn’t be more right … its the marriage…not the dress or the party…that you will be living with for as long as you are living with it…I still have my home made dress and my husbandfrom 1996, I wouldn’t change either choice.

  • sin_plomo

    omg “Goldie Hawn circa Overboard” has anyone seen this movie lately?? It’s so disturbing in terms of narrative but also Kurt Russell and Goldie Hawn so….

  • oliviafortune

    Just read the recap on town & country. “Many of her readers were shocked to learn she even had a boyfriend.”

    You must have felt like a total Carrie.

  • Katy

    I’m presently in the same boat. Already wanting to rewind and I haven’t worn my dress. I went to a salon of samples as time had ticked away. I was determined I would leave with a dress and though I’ve dreamed of a Rosie skirt and button up a la Diane Keaton, I, on a pedestal in front of my best new strangers, said “let’s get this one” while I wallowed in internal indecision so that it would “just be over.” In my blinded state I left with a floral lace a line dress…whoops. No returns!