Before It’s Too Late: 3 Unexpected Holiday Party Looks

Or alternatively, 3 outfits I would wear if I were not pregnant-as-fuq


Have we over-indexed on holiday party outfit recommendations? My sense is that you can never have too many, particularly because around these parts, holiday party outfit recommendations are essentially everyday outfit recommendations. Fine! Maybe not every day. But certainly every weekend. I, for one, like to put on pearl earrings and pair them with a headband (one of the Carrie Bradshaw-on-her-30th-birthday variety) while I sit on my couch in camp socks, eating yogurt, watching Father of The Bride Part 2.

Also, though, once vacation ends and we enter the true dead of winter, we’re going to need red turtlenecks and velvet hair ribbons and feather accents and shiny-ass earrings and a wrist that could be mistaken for the accouterments of a Christmas tree. I just know it. But we’re not there yet; on the contrary, we’re still in the thick of party season and in the event you’re sick of the most unoriginal and frequent outfit recommendation (see: the little black dress), here are three unexpected holiday party looks to try for yourself, or as I like to call them, three outfits I would wear if I were not pregnant-as-fuq.

For When You Want to Wear Pajamas to the Party

Have you ever considered layering your nightgown (I recommend linen over silk because of the static factor) over a turtleneck? In this look, I marry a printed Sleeper dress to a striped J.Crew turtleneck and ask one Maison Michel flat top hat with a pearl chain for a chin strap (!) to officiate the ceremony. There are sparkly socks to accommodate your holiday cheer, and while the pictured shoes are Manolo Blahnik, the footwear offerings of satin and green are vast. I trust you to make your own decision on that front.

For When You Want to Wear Your Jeans to the Party

I maintain that layering a peasant or Victorian-style blouse over a long sleeve white t-shirt and tucking both into a pair of white high waist jeans is an incredibly easy canvas to play with. Missing ingredients? Crystal-embellished sandals (yes, your toes will be cold, yes, it will be worth it — and in case you’re wondering, the photographed sandals are now 60% off on Net-a-Porter), dramatic earrings to catch the bows on your feet and a headband that adds at least two inches to your height.

For When You Just Can’t Get Out of Your Leggings

No sweat, my pet! They don’t call it athleisure and I don’t call it blathleisure (black tie athleisure) for nothing! Keep your leggings on. Have a field day with them. In fact, if you’re wearing a matching bra, keep that on too; I’m just going to ask that you style it over a button-down shirt (a silk or striped or plaid or leopard print one is fine if you’re not nuts about feathers) instead of under one. The real pièce de résistance here is three-fold: wacky boots (also 60% off!), a matching hair ribbon and those Christmas-tree accouterment wrists I’d mentioned earlier.

Now, are you thinking what I’m thinking? That the real magic of a great outfit is not so much in the actual clothes (though they’re great, don’t get me wrong) as it is in the way you wear them? Yes. Sure. Confidence and gumption are great, but more superficially, me thinks it’s time we (MR) make accessories — the true soul of any great outfit.

Photos by Edith Young. Modeled by Alisha Bansal

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  • Adrianna

    My work holiday party said “festive attire” which I interpreted as “cat print.”

  • Moe

    I would be asked if I was mentally stable if I wore the first or third outfit…

    • Gina

      I was thinking the same thing. Normally MR outfit recs are just cray enough that I can appreciate the ~creativity~ and ~cutting-edge-ness~ of them, but those two just went a taaaad overboard for me. Fine line between “ooh look at her!” avant-garde/free-wheeling and just I-feel-awkward-for-you, your-outfit-is-head-scratch-inducing-in-a-bad-way.

      • Caroline Christianson

        Ladies!!! When I see someone wear something outside the box, I’m only inspired and in awe of their self-assuredness and/or playfulness during this short time of youth/life/existence. I encourage you to take more risks in an arena that is temporary and fun (and, more importantly here, to only embrace those experimenting along these lines!!!)

    • Leandra Medine

      Hard disagree!

      • Leandra Medine

        Puhlusssssss, it’s the HOLIDAYS! you’re supposed to take a RISQUE!

        • LOL at wearing the first outfit to my v. conservative office holiday party.

          Might have been worth it for the reaction expressions alone…

          • TinySoprano

            Though outfit #2 was practically what I wore to my office holiday party and not a single engineer batted an eyelid! Obviously I need to amp up my game and go for look #3.

    • Jo Ho

      Totally agree with you Moe. I’m all for creativity but looks one and three are just plain ridiculous. Is that an actual nightgown or a dress made to look like one? Either way there is no way I’d wear any of these unless I was going to bed.

  • Natty

    thank you for confirming that i can, indeed, wear strappy sandals to a holiday party in December. I felt self conscious about my outfit choice for this evening.

    • lateshift

      I mean, you CAN…but sweet jeebus, why would you? #realtalk time: If the nightly lows in your part of the country are in the high 50s-low 60s: you do you, I guess. Live your best life. But if the temps are any lower…sorry, but no event – NONE – is worth risking frostbite over. And even if the outdoor exposure is minimal – like, cab to front door and back – the fact remains that 100% of people who look at a sandal-wearing human inside a holiday event, even the ones who give mad props to that person’s styling skillz, will be staring less with a gaze of admiration than with one of confusion, pity, or some combination of the two. In other words, someone who bares their feet in public between November and April will almost certainly be uncomfortable (as a red-blooded human who can feel temperature and pain), but will not actually look stylish or cool (since I believe a sandal-wearing 20-something is the image that appears in textbooks as the echt-illustration of the phrase “trying too hard,” and trying too hard is never attractive or cool.) I’m all for going against the grain, but the laws of nature are the laws of nature.

      (And no: tights with strappy sandals don’t do jack by way of protection… although I guess they might push the doable temp range maybe 10 degrees lower.)

      tl;dr. yep, strappy sandals DO look weird at this time of year. That is because, unless you live in a California- or Florida-like climate, they ARE weird. Everyone should live their best lives, but know this: a person who does this will not be trading comfort for style, because in this context, if they live in the Northeast or Midwest, they will almost certainly look both uncomfortable and unstylish. #TheMoreYouKnow

      • snakehissken

        This is really a matter of perspective. I’m from a place that’s so cold that people have “outdoor shoes” and “indoor shoes” and no one would ever be so rude as to bring their outdoor shoes into someone’s home. We weren’t even allowed to wear our outdoor shoes inside at school growing up.

        Over there, if someone is wearing sandals then she brought them with her and her enormous winter boots are sitting somewhere with the snow dripping off them.

        But I suppose you’re right that most people would still think that’s trying too hard, at least for a party at someone’s home. People just walk around in their socks.

        • Hil

          I love the idea of outdoor and indoor shoes! It’s what I do at home and I’ve thought about doing that for work even though it’s not normal and people would find it amusing. Where are you from? I need to know where this is the norm!

          • snakehissken

            Nowhere too exotic – Canada 🙂

            I live in the northeast US now, and I got the shock of my life when I went home for Thanksgiving with a friend my first semester of college and she walked right into her house and up the stairs without taking her shoes off.

          • Hil

            Yep, that’s where I am. Wish we could all learn to take our gross dirty shoes off!

      • TinySoprano

        You can if you’re in Australia 😉 In fact, anything short of mules is going to give you the worst hecking blisters…

  • Outside the box , doesn’t have to lack taste ! The second outfit is not only tasteless, but looks like you’re probably on the lamb !
    Dress The Part

  • Harling Ross

    TYSM for making white nightgowns a year-round, 24/7, night-to-day affair

  • Selena Delgado

    I need green satin anything, now

  • Amazing, the party looks has charmed me a lot. It’s really dashing.

  • Áine Hegarty

    I love the first two outfits!!! Amazing, Leandra!!! The hat and the dress in outfit one are so great, plus sparkly socks and Emerald green Manolos= Dream outfit. And then the red lipstick pop with all the white and tall headband. So well styled and fun. muchas praises.

  • Andrea

    You are absolutely insane and I love it.

  • That hat actually made my day!

  • DATowpe

    I could pull off #2 but it takes a special kind of person to pull of #1 and #3. That person is not me.