Dressing for a holiday party can be a tedious chore. You want to be festive without looking like Santa Claus, to stand out without being talked about. For me, the challenges of holiday dressing are exacerbated by the fact that I hate to spend money on things that I will not wear that often. I also run into problems because I am a habitual under-dresser. I often show up at a party looking like I am at the wrong party.
But recently, I’ve come around: what’s the point of a holiday party if you can’t wear something fun and look like you put a little effort into it? This year I pushed myself to get creative with my party outfits, using existing pieces and mixing in a few new things. Below, some ideas.
Cover Up
There’s an instinct to show more skin when dressing for a party. But covered up can be just as alluring, if the silhouette is right. The fit and flare of this cotton dress is kicky and it feels seasonal because the skirt is quilted. I like the zipper detail in the back, which breaks up some of the black.

This is a pretty tame outfit, but please note that I’m pushing myself here, because I hate wearing things that are fitted around the middle. A downside to having a relatively curveless figure is that there is only about a 2 inch differential between the circumference of my hips and that of my waist. I don’t cry about it, but I definitely envy my girlfriends who have a waist that flares out into some bangin’ hips.
I am so irrationally sensitive about my lack of a waistline that I will flinch visibly when people hug me around the middle. Frankly, I’d prefer that you say hello by putting your hand on my face and pushing me over. But since I discovered Spanx Tight-End tights (shown above), being hugged around the waist is less stressful, because these tights suck in your waist without giving you the dreaded waistband roll, or worse, flattening your ass. They are also completely opaque and don’t get shiny when you put them on your legs. They have once or twice given me the confidence to wear my most dreaded fabric, clingy jersey. What more could you possibly require from a pair of tights, except that they be free? Nothing, I tell you. Nothing.
Brights
I bought these yellow pants on a whim a few years ago. They aren’t the best pants to wear repeatedly (“Yoona’s wearing her yellow pants again”), but I have worn them exactly once, and they weren’t cheap. So I pulled them out to see what kind of holiday outfit I could come up with. Holidays are a good time to pull out the brights, because they are naturally festive and eye-catching. I think the outfit below would work really well for those work-related parties that you have to attend straight from the office. Throw on some extra jewelry, swap your pumps for some satin heels, and you’re ready to get all boozy and inappropriate in front of your coworkers. And yes, Tate here hates my blog.

Heavy Metal
The best fashion tip I’ve ever read is that you should wear things that you enjoy wearing, regardless of whether they are in style or not. This tip has potential for some grievous misapplication, especially if you are a grown man who enjoys wearing sports jerseys, but generally, I think it’s true. Because usually, you enjoy wearing things that make you look good, and who cares if what you are wearing is considered a trend of the past by OK Magazine?
I tell myself all this to justify my unhealthy penchant for harem pants, which were technically in style for 12 minutes in 2009, and maybe for like 2 weeks in 1992 when Aladdin came out. I love everything about harem pants, but mostly I like that you can eat a steak in them without having to unbutton them underneath the table. I got these bronze ones on clearance, and the metallic is fun for the holidays. I paired them with a metallic top and some fake gold cuffs to round out the theme.

The Twenties
My husband watches a lot of a show called Boardwalk Empire. If you haven’t seen it, don’t bother, because I’ll tell you right now that there are about fifty random guys in the cast, none of them are hot, and some are actively frightening. But the clothes are lovely, especially the dresses. The dress below has a drop waist that reminds me of a flapper dress, and it’s comfortable and easy. Wear your tallest heels with a drop waist, to avoid making your legs look shorter.

Sweater Girl
I love me a full length skirt. They are dramatic and unexpected in most situations. If you’re thinking that shorter people can’t wear maxi skirts, you may be wrong. If the fit is right (make it hug your waist and butt), a long skirt can be lengthening in a way that especially benefits the relatively petite, particularly when worn with a heel. If you are wearing a heel, make sure the skirt goes right to the floor.
The skirt below is wool, but it’s cut on the bias so it’s not overwhelming in its volume. Because it’s cut close on top, I paired it with a fuzzy sweater. I like that this outfit is monochromatic but has textural interest to keep it from being too boring. Plus, it’s warm! I think I’ll wear it to my firm’s holiday party this year.

Jump Around
I’ll usually take a pass on a dress if I have another option. I don’t know what my problem is, but I suspect that it may again be the shoe issue. Most dresses require that you buy a new shoe to go with them, and by the time I get to the shoes, my attention span for the outfit has usually run its course.
I suspect the outfit below is going to get a lot of push-back, but let me defend myself. First of all, this is a jumpsuit, but it is not a romper. I can think of maybe two people who can get away with a jumpsuit that ends in freaking shorts, and both are Kardashians. By the way, not to state the obvious, but if you often find that you are wearing the same thing as a Kardashian (especially Kourtney, but really, take your pick), it may be time to re-evaluate your wardrobe. This jumpsuit is the only one I own, and yes I realize jumpsuits are generally not very flattering on anyone. But how do you know it will be so terrible on you, if you don’t give it a try? My stylish friend Caroline likes them, and ol’ Yves Saint Laurent has been making them for decades, so there, they can’t be all bad.
The jumpsuit below has elicited strenuous objections from my husband, who hates jumpsuits, and especially hates this one, because, as you can see, it is cut to the navel. Personally, I think that if you’re going to get skankified, a low-cut top is preferable to a too-short skirt, especially if you are not well-endowed up above. I mean, the stakes are pretty low–if my boob falls out, congrats, you’ve now seen a breast in its full A-cup glory. Nonetheless, Tom refused to go anywhere with me in this jumpsuit until I got something to put under it. Hence the lace tank, which I think actually classes it up a bit and takes it safely out of Kardashian territory.

What are you wearing to your holiday parties this year?