What to Wear Where: Unexpected Holiday Looks

I love sharing my What to Wear Where posts and this month I wanted to make it extra special. We are all busy running around and trying to decide what to make for holiday dinners, what white elephant gift to purchase, and who on earth picked ours names in the grab bag. Not to mention that you’re also busy playing Santa and your kid’s list is filled with the must-have items that are sold out everywhere! What to wear is the least of your worries… until your holiday work party rolls around and you feel disheveled and uncomfortable. But don’t worry, because I am here to help!

Here are 10 looks meant to inspire your holiday attire this season and they’re all just a little quirky and unexpected!


  • Unexpected Holiday Looks 1 of 11
    shorts main

    These 10 looks will have you thinking twice about how you dress this holiday season. 

  • Lumber Gal 2 of 11

    Plaid, fur, and leather are all working together here and yet, the look is anything but rustic. It's all pure chic.

    Shirt available at J.Crew, $89.50

    Boots available at  at Forever 21, $39.80

    Skirt available at H&M, $99

    Vest available at  Aeropostale, $31.80

    Earrings available at Monsoon UK, $68

  • Little Black Outfit 3 of 11

    Head to toe black? Couldn't get anymore glamorous than this insanely inspired 60s outfit.


    Dress available at Zara, $49.90

    Boots available at Macy's, $159

    Earrings available at Aldo, $12

    Sunglasses available at Karma Loop, $23

    Bag available at Asos, $46


  • Kimono Style 4 of 11

    Look extremely stylish, and stay completely comfortable, as kimonos feel just like lounge wear. Try it with a fun hairstyle like this one


    Kimono available at H&M, $79.90

    Tank available at Yoox, $59

    Joggers available at House of Fraser, $155

    Heels available at Forever 21, $36.80

    Nail Polish available at Net-A-Porter, $15

    Lipstick available at Etsy, $7.50

  • Winter Boots 5 of 11
    fur booties

    A simple belted dress works for almost any occasion, but add fur booties and a tartan scarf and you have a fun, powerful holiday outfit. 

    Boots available at Forever 21, $42.80

    Dress available at Forever 21, $15

    Belt available at Old Navy, $10.50

    Watch available at Fossil, $95

    Scarf  available at Amazon, $33

  • Short Shorts 6 of 11

    Shorts in the winter? Yes, because some places (like Miami) are not cold and if you're in a climate with colder temperatures, then you can easily wear tights. This is no different than wearing a skirt. Try it out!


    Sweater available at Madewell, $98

    Shoes available at Opening Ceremony, $200

    Shorts available at Oasis, $65

    Bag available at Aldo, $35

    Ring available at Aldo, $10

    Lipstick available at Elizabeth Arden, $25


  • Inspired Glam 7 of 11

    I've loved the look of a dramatic maxi skirt and sweater since I saw Jenna Lyons on the red carpet at the Met Ball. Her style is an odd, yet perfect combination and you should definitely try and put it to use this holiday season.


    Sweater available at TopShop, $60

    Shoes available at Macy's, $165

    Skirt available at TopShop, $136

    Bracelet available at 2B, $17.95

    Smokey eye image source

  • Casual Denim 8 of 11

    Denim might seem too casual for the holidays, but not all parties are that elegant. Holiday attire is not necessarily required. A bold, bright-colored clutch and metallic heels dress up the look just enough to make it party worthy. Take it up a notch with an up-do and some red lipstick. 


    Watch available at House of Frasser, $220

    Jeans available at Burlington, $19.99

    Bag available at Gap, $40

    Heels available at BCBG, $225

    Shirt available at H&M, $29.95

  • Plaid Blazer 9 of 11

    A plaid blazer, crushed velvet heels, and statement earrings just scream holidays. But pair them with a dark denim and the look becomes more casual, unexpected, and fierce. 


    Clutch available at Daily Look, $50

    Shoes available at Modcloth, $45

    Blazer available at Target, $34.99

    Earring available at Asos, $29.40

    Shell available at Piperlime, $79

  • Boy Meets Girl 10 of 11
    boy meets girl

    A school boy blazer and a girlish mini is the perfect combination for a very feminine boyfriend-inspired look. 


    Shoes available at ModCloth, $40

    Blazer available at J. Crew, $198

    Bag available at Maggie Bags, $149

    Skirt available at Forever 21, $40

    Nail Polish available at Sephora, $18

    Top available at H&M, $17.95

  • Blue Suede Shoes 11 of 11
    Plaid skirt

    The shoes, lips, and nail polish are bold while the outfit remains easy breezy. Surely not something one would expect during the holidays, but it will be very refreshing for all those party-goers to see you so relaxed. 


    Shoes available at Nordstrom, $180

    Skirt available at Madewell, $98

    Sweater available at Topshop, $60

    Nail Polish available at Macy's, $15

    Necklace available at Amazon, $79

    Lipstick available at Etsy, $7.50


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