Dressy Holiday Outfit Ideas

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Phew. What a year. And we’re topping it off with a holiday season like no other. Normally the holiday is a season for celebrations, parties, and gatherings. With the endless events come the endless amounts of outfits you need for every different event.

Now, I know we’re in a pandemic this year, but I’m still hearing about people having plenty of virtual holiday, Christmas, and New Years celebrations. Or their own mini celebrations at home. I know the temptation to stay in sweatpants is strong (really strong). But why not throw on something nice for the one hour you’re on the virtual party? Or at least throw a nice top with your sweatpants. Heck, you can still dress up while you’re at home! With all of that in mind, I thought it would be nice to share a round-up of festive dressy holiday outfit ideas for every kind of party during this season. Virtual or not, there’s no harm in being prepared.

Dressy Holiday Outfit Ideas

To say I tried to make this extensive is a bit of an understatement. I tried to cover just about every level of dressy I could think of from formal to ugly sweaters. But by all means, if you think I missed a category….don’t tell me.

Business Casual Parties

Let’s be honest, business casual parties typically translate to the good old office party. Also, more likely the ones where you’re going somewhere right after work or during the work day. So you’re likely going to were whatever you wore to work. For this holiday party outfit, I would aim for adding small holiday touches to your outfit, instead of going overboard.

What does this mean? First, stick to typically work wardrobe, but add one “fun item”. Maybe you do a sparkly necklace with a red or green outfit (but maybe not both colors, restrain yourself). Or you could do like I did below and find a dressy piece of plaid clothing. It’s a great way to give your outfits a holiday spin without going overboard.

Since many of these outfits are old, I’ve linked to some more dressy ideas below that will help make your business outfit pop for a holiday party!

Cocktail parties

Holiday cocktail parties are sometimes the bane of my existence. Why? Well, they’re typically after work and they require a dressy outfit. So I have to go home and get dressed up instead of going home and staying in with a warm drink.. My introverted-ness does not approve.

But a cocktail outfit we must, so a cocktail outfit we will. The easiest route to go is a little black dress (preferably with long sleeves in the winter) or any other cocktail dress, but I’ve been having some fun experimenting with different options the last few years.

One option to try out is wearing a midi skirt with a leotard like I did below. A midi skirt with a fun pattern will create a fun look for the evening. I like then pairing them with leotards because that will create a smooth line at your waist and guarantee that your shirt doesn’t come untucked. I then like pairing them with a festive, colorful shoe to top off the look.

Another look I’ve been experimenting with is the little black jumpsuit (instead of the little black dress, haha). Jumpsuits are great because not only are you more comfortable, but you’re warmer in them. Additionally, they’re easier to dress up or down like I did here. Here it’s a dressy look, but I could easily re-wear this for a more casual look.

Finally, who says pants are just for the boys? I love pairing a cute blouse with ankle pants and pumps and wearing that to a cocktail party! Just make sure that you feel comfortable and confident.

Here are some great idea for your cocktail party pieces!

Semi- and Formal Parties

I like to think that semi-formal and formal outfits for woman are fairly simple during the holidays. You just need to ask yourself a few questions: how long should my holiday dress be and can it be sparkly? For most semi-formal parties, I would aim for a knee length dress and for a formal party I would go floor length.

When it comes to sparkly, I say why not? If you don’t have an answer to that question, then yes, wear a sparkly dress. You can’t tell it that much from the picture, but the red dress I’m wearing below is actually just as sparkly as the striped one. But I would wear the red one to a family holiday party while the white outfit is more appropriate for a new years eve outfit.

Here are some great options for your holiday parties!

Virtual Celebrations

By now, I’m sure you’re well versed in looking good for being on screen. Whether it’s been for work or another family get together, we’ve all had to do it at this point. So I only have a few quick tips for this one.

First, do your hair and make up. Don’t look like you just rolled out of bed. At the very least run a comb through your hair and throw some lipstick on. But really, people can tell when you didn’t try and you’re here for the party, so at least look like it.

Second, no one can see what you’re wearing on bottom, so have fun with what you’re wearing on top. Throw on your favorite cute top and fancy earrings and you’re ready to go.

If you really want to get into it, pull out your favorite Christmas party outfits and put them on. Just have fun with it. After all, you didn’t have to leave your house and drive somewhere in crappy weather, so no matter what, this party is a win.

Ugly Sweater Parties

These parties are my favorite. I just love seeing everyone’s ridiculous sweaters! Luckily, getting dressed for these is super easy. Just find a crazy sweater and then wear whatever feels comfortable on bottom.

Casual Parties

Next to ugly sweater parties, casual parties are my favorite. They’re also the ones you’re most likely to see this year. These parties are perfect for outdoor social distancing, zoom, or just at home with your loved ones.

Why do I love them? They’re the perfect occasion for a sweater and jeans (my two favorite things). I also love it, because it’s super easy to make your outfit casual, but nice by adding just one or two cute pieces. If you check out my outfits below, you’ll see how I did that through items like metallic boots, a faux fur vest, plaid shoes, and faux leather leggings.

For this year, my number one suggestion for causal parties is faux leather leggings. I think they’re perfect no matter how your gathering is being hosted. You’ll be comfortable the entire time, but you’ll still look like you tried.

There we go! Your A to Z of dressy holiday outfit ideas…even if you’re like me and you have no intention of leaving your house this holiday season. You can bet I’ll be taking my own advice on those leather leggings and virtual parties!

Out of curiosity, how many virtual parties are you going to this year? Is it too many?