Summer Wedding Outfit Jeopardy

Because Wedding Season has only just begun.


Cady Heron became a star the moment she provided the Mathlete state championship-winning answer: “the limit does not exist.”

We could then take that very same answer and turn this into a game of Jeopardy, with Cady’s quote as Alex Trebek’s clue and the correct response being, “If it begins in May, when does wedding season end?”

Get it? Because wedding season, like high school math class in general, seems to never, ever end. It, like the hopeful love we celebrate, is eternal.

(I’m not sure I know how Jeopardy works, btw.)

But I do know how clothes work! So what in the hooternanny are you supposed to wear come mid-July when you’ve worn through every slip dress, Zara frock and repurposed bridesmaid gown in your wardrobe repertoire? (If this looks familiar, that’s because it is, by the way — thought we’d remind you…)

What are: culottes, midi-skirts and flats.

Wide Leg Pants That Are Just as Dressy as Your Dang Dress

My guess is that by now you own at least one pair of culottes, right? Seize the wide leg! Counter it with a blouse that could be worn off the shoulder. You can DIY your own helicopter wings or forgo them all together. Wear really tall, fun heels because all wedding shoes should make your feet look like a Pinterest board.


(Pictured: Rosie Assoulin top and pants, Charlotte Olympia wedges)

The Bottom-Wear Equivalent of Three-Quarter Length Sleeves

In the event you have not started collecting straight ankle length skirts, may I politely recommend that you get your ass to it ASAYesterday. If 2014 was year of the roomy pant, 2015 is on track to become year of the cropped maxi skirt. That sounds paradoxical, but that’s only because it is. Counter the pin straight nature of your skirt with a voluminous top that may or may not allude to your being pregnant. Drink a lot of alcohol to throw the bridal party off.


(Pictured: Rosie Assoulin skirt, Vika Gazinskaya top, Olympia Le Tan clutch, Christian Louboutin-by-way-of-the Real Real mules)

Shoes That Give You Happy Feet

This look is much more about the region south of the ankle. If you’re looking to wear flats to an imminent wedding, don’t ask questions, just do. The best way to achieve this is by opting for a dress that hits your ankle in a capacity similar to the above skirt but perhaps does so in a slightly more formal fashion. The con: You’re a bit shorter. The pro: You’re the most comfortable maid in the room.


(Pictured: Alessandra Rich dress, Michael Kors sandals, Shourouk basket)

You won! Now take your prize money to the nearest open bar and run!

Oh god, did the bride ask you to “say a few words,” but you have zero? Let us help. And check out our latest office apropos, for more summer styling tips. 

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  • Ari Camacho

    Love the last two looks!!

  • Stephanie

    “Drink a lot of alcohol to throw the bridal party off.” = The best line of the morning! Seriously, though, great inspiration for summer wedding looks.

  • Natali

    First outfit is SO amazing, it’s totally red carpet worthy, while the 2nd outfit is something I would totally wear to a wedding. 🙂

  • monkeyshines
  • The sleeves on that Alessandra Rich dress are killin me

  • I am going to a wedding in September and have already decided to wear a co-ord short suit. For example; OR a short version of this ACNE suit; which I have stashed away in the back of my wardrobe – OPINIONS ALWAYS WELCOME WITH OPEN ARMS xoxo

  • thank you for dressing and prepping me for these summer events coming up. AND best part, i don’t have ta shave the legs.

  • Carooo

    what about what to wear to your own summer wedding when you’re not sure your dress will be ready on time ? 🙂

    • Amelia Diamond

      oh no. is this happening to you right now?? what’s your max budget and are you open to slip dresses because i’m about to go duck hunting but by that i mean dress hunting for you

  • Catalina
  • Taffeta culottes! Huzzah! I had to wear a flower girl dress in 1992 that was made out of approximately the same fabric

  • parkzark

    I want those charlotte olympia wedges UGGHGHGHGHGH

  • Kenns

    Leandra-all three looks are gorgeous and totally unique! I am definitely going to incorporate them in whatever dressy occasion presents itself. The Alessandra Rich dress is amazing!

  • Lua Jane

    Rosie Assoulin is a pure genius. And so is Vika Gazinskaya..seriously first two outfits slay! And I need those mules in my life, because pastel and the dainty bow is exactly how I feel at the moment.

  • Restless Blonde

    The star dress *.* Loooove it! And what a pity I don’t have any wedding this summer 😛

  • Bella Charlwood

    Where can i find these Michael Kors sandals!!

  • All of these outfits are amazing, but I loooooove the Alessandra Rich dress.

  • AlexaJuno

    …And the hunt for a silhouette Leandra can’t pull off continues. Slay.

  • Quinn

    Thank you for this post!!! I’m obsessed with the Alessandra Rich dress. Any chance you need to get rid of some of your amazing stuff? Man Repeller second hand shop? doooo it.

    • @disqus_Dlqy0Z4j4i:disqus YES!! I totally second that!!!

      MR: WE WANT YOUR CLOTHES!! haha. xx

  • Lauren at adorn la femme

    I am falling off my chair over those wide culottes! The Charlotte Olympia wedges are the quintessential shoe that will put the bride’s shoe to shame!!

  • Alba B.

    The first is my favorite, but on my pencil your choices find their paradise…@least they are far better than those outfits of the MET GALA!!!

  • Alba B.

    The first is my favorite, but on my pencil your choices find their paradise…@least they are far better than those outfits of the MET GALA!!!

  • All of the options are super cool, but the second one stole my heart. I love how far it is from the regular wedding guest style. I mean it certainly depends on the wedding, but at most that I attended the dress code was tacky and way too shiny dresses, which seemed to say ‘I tried way too hard, but the outfit still sucks’. And that ‘nude’ thights that are actually visible. Ugh.

  • Emily Valentine Parr

    the last look is a beauty!! love the shape and playful star print xx

  • some of my favorite looks of yours to date! and that is saying a lot bc i love pretty much all of them. you look so happy and pretty and simply diVINE, dahling. i need rosie assoulin in my closet so bad.

  • Hannah Cole

    I just LOVE that Alexsandra rich – every day is a happy day with a dress like that

  • vzukelman

    I LOVE the second outfit–the top by Vika G is beautiful!

  • Marianne Ronsse

    Hi team MR, I have a question for you: do you have any advice on what to put on top of a wedding outfit? I know it’s supposed to be a summer wedding, but sometimes, despite summer, it’s cold and rainy, and it can get cold during the evening as well… So what would you pair such an amazing outfit with? Without ruining it entirely of course.
    Thank you

  • Sarah Keller

    Those ginko leaf earrings are too legit to quit. Where do they come from?

  • Josefa Santander

    amazing! genius!!!

  • Ashley Harris

    Okay, that Vika Gazinskaya top and long skirt. I’ve made it my mission to replicate it for a wedding that my husband is a best man at, and well we all know that I’ll have to make my own while he’s tending to all those various duties and leaving me to fend for myself. So, a killer outfit is needed to avoid small talk and just have “OMgersh your outfit, I leeerrrvvvveeeee it.” And jump into a better convo about blogger style and stuff instead of “how’s your dinner that is the exact same as mine why did i bother asking that i know the answer” convo. So. All that to say is, I can’t spend over a grand on a top. I’ve got the perfect skirt. But i need a more wallet conscious option for that top please. Or since you’ve worn that one a few times, can I borrow it for a night? Cool , thanks. -Ash

  • Great tips Leandra, love what you have done and as a result are fabulous photos that we can see at your article. Well done!
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  • The star dress suits my personality. I like comfortable and clean look, so it is my kind of dress. I would match sapphire or emerald ring and bracelet to it instead of a funky stacking. The flats are exactly my choice.


  • DMC

    I’d give anything for that Vika top.

  • lexi

    Love all of these – especially the black tops. Really cute!
    xx Lexi @glitterinclexi | Glitter, Inc.

  • Selina Moses

    I find that a jumpsuit and kimono or a 50s style dress and kimono works perfectly for a hot weather wedding. I like the idea of culottes though

  • itllbealrightonthenight

    Too white. But gorgeous.

  • Wedding season most definitely IS here. I just went to one last weekend myself. I enjoyed this post =)

  • Hereshoping Themayanswereright

    Love 2 and 3 – That little black top is absolutely darling on you! The last look is just gorgeous and dreamy.

  • ktbkes

    u look amazing, and these all rock, but how about some cool options that are a little (or a lot…) more affordable? We need your help!

  • The only thing I can think about now is making sure my feet feel like a Pinterest board. Thanks, Leandra!

    Hannah | The Outfit Repeater

  • Those green pants are TDF

  • I cannot put into words how much I love this website. I laugh out loud every time I read an article. Pair fashion humor with Mean Girls references? Good God I’m in. xx

  • Cropped maxi!?!? And I thought math was confusing…Loving them looks! 😀

  • ”Wide leg pants that are just as dressy as your dang dress” Yes!!! And more comfortable.

    Julia xx

  • I still can’t accept culottes! Just no…

  • LOVE THE BLACK SHIRTS AND THE DRESS!!! I would tot wear that dress – and I absolutely love that you don´t overproduce your hair or make up – you look stunning – its SO cool that you are so natural and just have fun with fashion. LOVE IT. #inspiration. thank you

  • Hollene

    Those KORS sandals are DOPE. They’re not on the page they’re linked to, though! Help?!? I heart them so much.

    • Leandra Medine

      I think they may have sold out! Let me do some investigating.

      • Hollene

        Muchas gracias!

  • monkeyshines
  • I love ALL looks, but I wont wear white dress to a wedding 😉

  • love that black top

  • Jenny

    All dresses are very beautiful. Thanks for sharing such a useful blog with us.
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  • Nikawa

    All of these outfits are amazing

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  • 2tekvn

    Love 1 and 3 – That little black top is absolutely darling on you!
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  • alex anderson

    I like you because pharse “the limit does not exist”. Thank you very much! I give you a “điện thoại cho người già”, i like it

  • alex anderson

    I like you because pharse “the limit does not exist”. Thank you very much! I give you a điện thoại cho người già (details:, i like it.