It’s almost December, which means pretty soon we’ll be overwhelmed by holiday parties and other sorts of gatherings. I love a good party, don’t get me wrong. Actually, that’s an understatement. I LOVE parties, certainly more than most people, but that’s not to say I don’t recognize all the stress that surrounds these holiday festivities. Probably the most stressful part of holiday parties (at least for me) is figuring out what to wear. You most certainly don’t want to be dressed inappropriately for a holiday party. If you’re attending an annual event you’ve been going to the past few years, then hopefully you’ve got the dress code figured out. If you’re attending your first work holiday party (cough cough, that’s me) or any other holiday party for the first time then you have a few options to hopefully reduce the stress of being well-dressed:

And as Oscar Wilde so eloquently said, “you can never be overdressed or overeducated.” So true!

1) Find someone you feel comfortable with and ask them advice on what to wear. (This only works if you know someone else going to the same party, so great for a work function, but not so great if your significant other is dragging you along to a party and you’ve never met the host or other guests attending). Side note: don’t ask someone you wouldn’t take regular fashion advice from…like the person who looks like they never grew out of their college wardrobe or the person who thinks it’s appropriate to wear see-through tops to work…

2) Err on the side of being (slightly) overdressed. You definitely don’t want to show up underdressed, that makes you look like you don’t care and that you were out of the loop. BUT if you show up a little overdressed it’s kind of a win/win. A) everyone will be envious of your outfit and wish they’d dressed up a little more, and B) you’ll feel confident/comfortable, and C) it also makes you look like you really want to be there…which you might, but there are also plentyyy of holiday functions that we don’t want to be at. Am I right?

3) Dress up your outfit with jewelry/other accessories. If you take a simple, black dress and dress it up with jewelry then you have a more formal look…that’s not rocket science, and it’s much safer bet then showing up in a semi-formal black dress and being wayyyy overdressed. Another idea here is to wear a fun blazer/jacket that can either dress your outfit down or up. Once you show up to the party you can keep said jacket on or take it off depending on what guests are wearing. Does that make sense?

Below I’m sharing one option that I think could work for a variety of holiday functions. You can even pair the dress I’m wearing with a blazer, or just by itself and wear it to work, making it super easy to just throw on a fun jacket, a different pair of shoes, and head straight to your holiday function afterwards.

What I love most about this look is how mixing this fun, flirty fringe dress with the leather jacket makes this outfit a little edgy. I’ve been wearing these OTK Goodnight Macaroon boots on repeat lately for a few reasons: A) they are really comfy to walk around in, B) they go with pretty much everything, and C) my legs are so pale/they keep my legs warm instead of wearing tights! If you don’t already own a pair of OTK boots then I highly suggest you get a pair, and these Goodnight Macaroon ones are such a great steal. They come in a few other colors, and I’ve linked the boots below!

jacket: Theory (similar here, here, here) • dress: Banana Republic • boots: Goodnight Macaroon

the scoop: This jacket is amazing! I splurged on it last year at Second Time Around (an upscale resale store…but the tags were still on it, so it was brand new!) Investing in a real leather jacket is something I can justify because you’ll have it forever! Leather jackets are always in style. Always. // This Banana Republic dress (currently 50% off) is so cute and really comfy! I’m wearing a size 0 and it’s a little loose, but not too big. I might get it tailored or just live with it a little larger than I’d prefer. // These boots! You NEED these boots. They are really well made and super affordable. I’m wearing a size 37 (typically wear 6.5-7.5 in boots). Below is their sizing guide, but basically order down.

Happy Monday! Hope you have a great start to your week!