How to Dress for 3 Unexpected Winter Break Occasions

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When preparing for winter break, most girls think about dressing for New Years parties, Christmas dinner, and cozy evenings by the fire. While these are all important things to think about, here, darling readers, is my top three list of the lesser-known Winter Break occasions you may be faced with before you head back to school.

Night Out with a Group… That Includes Your Ex

Winter break outfit for a night out with a group including an ex

Scarf, Jacket, Tee, Boots, Ring, Brown Bag, Black Bag, Bracelet, Jeans

If you go to school far away or just don’t see your HS friends often, there’s a 90% chance that at some point over break, you’re going to be invited out for dinner or drinks with a big group to “catch up.” This should be fun, but can also be potentially awkward, as you’ll likely run into an old high-school fling (or, like one of my best friends, literally run into them- aaawkward).

My best tip in this situation is to dress simply, but elegantly- no ruffled uber-minis or cleavage-baring tops here! Your outfit should show you off, so stick with timeless, well-fitting pieces, like a great structured jacket paired with skinnies and high leather boots. I love this great black bag from Dooney & Bourke – a staple item! – but, for a more affordable option, this brown bag from ASOS looks luxe at a fraction of the price. Simple gold jewelry and a soft white scarf finish this effortlessly stylish outfit.

The Day After the Night Out

Lazy winter day outfit: Maxi skirt, button-down blouse, cozy cardigan, comfy accessories

Cardigan, Shirt, Beret, Purse, Black Ring, Red Ring, Moccasins, Maxi Skirt

Another occasion no one talks about dressing for is the day after a late night out. When you wake up and wonder why your mouth tastes like a dead raccoon and your hair could double as a bird’s nest, you’re going to have to get out of bed and make yourself look presentable for whatever activities you have planned… and it won’t be fun.

This look mixes preppy polish with a boho silhouette. Instead of slipping on sloppy sweats or constricting jeans, pull on a gorgeous red maxi skirt, and winterize it with a striped oxford and a navy cardi. Comfy moccasins and a cross-body bag are functional, but stylish, and some eclectic rings add a touch of glamour. Add a loose beanie and sunglasses (if necessary) to disguise second-day hair and tired eyes.

Random Party Invite

Winter party outfit: Red dress, statement tights, mary-janes, headband, festive makeup

Headband, Tights, Heels, Lipstick, Black Nail Polish, Gold Nail Polish, Dress

At some point during the holiday season, you will be called upon to attend a random party, whether it’s a friend of your parents’ dinner party, a new years soiree, or a confusing invite from a friend to a ‘festive’ dress party. You’ll want an outfit that’s stylish, but still practical, so you can stand around answering each individual dinner guest’s question: “So how’s college?” (Kill me now.)

Channel a little Gatsby-esque glamour with a flapper-style headband and retro tights. This beautiful dress combines cutouts with rich red velvet for an effect that’s both winter-appropriate and utterly flattering. (Bonus: the dress is on sale right now, as Ashley mentioned earlier this week! ) Little black Mary Janes are comfy but cute, and gold accent nails pop on a black backdrop. A great red lip keeps your look classically elegant.

What do you think?

Have you encountered these occasions? Would you wear these outfits? Got anymore events you didn’t expect over the break? What’s your favorite break activity? Leave any thoughts, questions, suggestions or grade school crush’s initials in the comments below!

9 thoughts on “How to Dress for 3 Unexpected Winter Break Occasions”

  1. THANK YOU for this. My friends and I are planning to meet up for New Year’s, but an ex is going to be there. This basically saved my life.

  2. lol @ “mouth like a dead raccoon”. we’ve all had those mornings… I love the outfit for seeing an ex. I was freaking out this one time about what to wear to see an ex a year after a messy breakup and ended up not going to the party cause I was so indecisive..I coulda used this post haha

  3. @marianne. I saw that red dress from a previous post and decided to get it and use it as my NYE dress and it isnt as bad as it looks, though I still think I’m going to wear some black stockings with it.

  4. @Marianne I would wear those hose under a longer dress so that the top part would be covered MOST of the time

    I’ve also worn that style to school before (in high school, before they got RUNS in the sheer part ugh) and a female teacher I didn’t know complimented me on them, saying she “had to get some for going out”

    You can get away with bold stuff like that when the rest of your outfit is polished! Just keep the rest of your outfit less Ke$ha, more girl-next-door/model off duty/glam.

  5. I actually love the dress in the last spread, but after checking it out – it is SO SHORT! I doubt you could sit down, let alone bend down to pick something up, or dance with your hands above your head….!

    And with those hose… not what I would wear to a family dinner :p

  6. I love this blogpost!
    I always get reeally nervous when I know I am going to see my ex and end up trying too hard with my clothes, which usually looks a bit awkward! This will definately come in handy sooner or later!


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