So Many Holiday Parties and Nothing to Wear—9 Looks for Every Occasion

It’s been a minute since I’ve had to prepare serious looks, so this holiday season, I’m looking forward to coming properly to every single event, no matter how casual. It’s been almost three years since I’ve seen so many friends, and this year feels like a reintroduction to the world. The long time away from friends can feel like an obstacle to overcome, but I actually love that we can skip the small talk and get straight into the thick of it. I imagine many of my friends have changed, as have I, and I’m hoping the outfits reflect that.

Being the obsessive shopper that I am, I have plucked nine outfits from Instagram that are worth re-creating for all the parties you plan to attend this month. I'm talking plumage, bling, not-your-average sequins, and beyond, so keep scrolling to see the statement outfits that make winter look fun.

1. Button-Down Shirt + Mini Skirt + Heels
The best 2021 holiday party outfits: button-down shirt, mini skirt, and heels

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What a fresh way to style a button-down! It’s hard to make a feather-trimmed skirt look laid-back, but Mimi nailed it. Keep the jewelry and accessories to a minimum in order to let the star of the show do her thing.

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This is one of the few button-downs that can be equally dressed up or down.

A little bit Cruella, a little bit Cher.

Evidence that Hot Girl Summer is a mindset.

2. Off-the-Shoulder Top + Maxi Skirt + Belt
The best 2021 holiday party outfits: off-the-shoulder top, maxi skirt, and belt

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@raayya

When it comes to dressing up, Raya is my queen. Her ensembles always expand my range and inspire me to step out of my comfort zone. This voluminous skirt is so timeless. Perhaps my favorite part of this look is the heavy metal accessorizing, which makes a classic outfit still feel very current. In case you haven’t heard, the maxi skirt is here to stay, so it’s worth getting ahead of the trend now.

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Cinch all your blazers and sweaters this winter with this statement belt.

Chunky silver jewelry is all I feel like wearing lately.

3. Cut-Out Dress + Statement Earrings + Mini Tote Bag
The best 2021 holiday party outfits: cut-out dress, statement earrings, and mini tote bag

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I'm loving the barely-there cut-outs on this long Jonathan Simkhai dress. A hint is more than enough. Pair your cut-out dress with statement earrings and a mini tote to stay within the minimalist theme. 

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4. Front-Tie Top + Trousers + Gold Accessories
The best 2021 holiday party outfits: front-tie top, trousers, and gold accessories

Photo:

@thevisuelofgrace

Front-tie tops are some of the newer ’90s-inspired pieces on the market this year. Style them with tailored pants for even more attitude. Now, where’s my espresso martini?

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White pants look so fresh in the winter.

These make it look like you have more than one piercing.

5. Sparkly Dress + Matching Accessories
The best 2021 holiday party outfits: sparkly dress and matching accessories

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A sparkly dress is practically synonymous with the holidays, so you might as well lean in. Disc sequins are a cool way to partake in the trend without looking played out. Match the accessories to the dress—we don’t want to distract everyone from the main event.

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This dress is begging for a slow-motion dancing moment.

6. Plaid Skirt + Fitted Top + Mid-Calf Boots
The best 2021 holiday party outfits: plaid skirt, fitted top, and mid-calf boots

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This midi skirt is the older sister of the pleated-mini-skirt trend we saw blazing all spring and summer. The mid-calf boots are the perfect height for this length skirt and look super cool in a retro way.

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7. Metallic Separates + Cowboy Boots
The best 2021 holiday party outfits: metallic separates and cowboy boots

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As we venture into the era of the Metaverse, a space-cowgirl outfit is probably most appropriate. Metallic separates are one of the more challenging outfits to get right but have a high payoff when done well. Stick as close to the same hue as possible, and use texture to add interest to the look. And of course, finish it off with some cowboy boots.

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Chain-metal tops don’t have a good track record in my book because they rarely fit, but this one looks like it has enough space to fit a lot of body types.

8. Sheer Skirt + Button-Down Shirt + Pointed Heels
The best 2021 holiday party outfits: sheer skirt, button-down top, and pointed heels

Photo:

@annabelrosendahl

Sheer skirts are one of my favorite trends this year. When it comes to styling them, reach for button-downs and simple tops as shown. This sheer lace skirt does a good job at obstructing some of the transparency, so don’t be shy.

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Wear this top over the sheer skirt, and add a belt to create an A+ ’fit.

9. Corset + Hair Bow + Stud Earrings
The best 2021 holiday party outfits: corset, hair bow, and stud earrings

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Wear this outfit to a friend’s house party, and bring all the cheer.

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