Fall/Winter Fashion
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Holiday Party Dressing with Ann Taylor

Holiday season is in full swing, and that means holiday parties! I’ve had tons of requests for various types of holiday party outfits. Some are attending galas, many have requested “holiday casual” outfits, and there’s everything in between.

We all want to shine a little brighter at holiday time, and one place I can always depend on to find sophisticated and feminine party pieces is Ann Taylor. I’m excited to partner with them on today’s post to share two party looks that will take you just about anywhere this holiday season. Both outfits feature this flare sleeve turtleneck tunic sweater.

You know me — I love a good sweater, and I know a good one when I see one. This sweater is elegant and refined with a nice chunky knit that’s not too heavy and the perfectly relaxed turtleneck. The contrasting ribbed stitch adds just the right amount of texture, and the flared sleeves are fun without being so voluminous that they get in your way.

In my opinion, there’s nothing as classy or versatile as a black turtleneck, and this one takes it up a notch to a tunic that’s the perfect length for pairing with faux leather leggings — another classic holiday party piece.

Okay, I’ll be honest, I haven’t been much of a fan of faux leather leggings until I pulled on these faux leather ponte leggings.

These are unlike any other faux leather legging I’ve tried — they’re thick and luxe plus they have a ponte knit back, which is so much more comfortable to sit in and keeps them breathable. I also like the seaming detail up the front and back.

Speaking of the back, notice how this sweater is just the right length for covering the essentials without adding extra volume as some tunics do.

For size reference, I’m wearing a small in the sweater and 6 in the leggings.

And because it’s cold, yo! I went with booties for both of these looks — but not just any booties. Take a look at this tortoiseshell print heel. *swoon*

These booties are just beyond. The best part, though, is that the heel is just 2 1/2 inches. I can walk all night in these shoes without sacrificing an ounce of style.

When wearing an all black outfit, accessories are key. I decided to go with a statement earring and allow the details in the sweater and leggings to stand alone, but you could certainly add a fun necklace if you wanted to.

I fell in love with these pearlized fabric earrings. They keep the outfit classy and sophisticated, and the ivory pearls provide a nice contrast against the black sweater and my dark hair.

I topped off this first look with a houndstooth wrap coat. Isn’t the black and white houndstooth pattern the perfect compliment to the all black outfit?

With the large shawl collar, it’s a little more drama than I typically go for, but I couldn’t resist this piece. If you’re looking for a statement coat to add to your winter wardrobe, this one is cozy and warm and looks beautiful over neutrals, pastels, jewel tones… pretty much everything.

But I couldn’t stop at just one look with this gorgeous sweater. I also wanted to show you a slightly dressier look that still has a modern elegance to it, so I paired the sweater with this shimmer pencil skirt.

This skirt is a made of a marled knit fabric with both silver and gold threads so it catches the light as you move around, and it goes with any metal you may be wearing in your accessories.

It’s also a convenient stretchy pull-on style with a wide interior elastic waist band, so hello comfort!

I’ve never tried pairing a tunic sweater with a pencil skirt before, but it’s a fun way to change up my look without stepping too far outside of my comfort zone.

When planning your party looks, don’t neglect your accessories. I added this foldover satin clutch in lime gold for a fun pop of color, and how fun is that bow???

I also wore this crystal pearlized stretch bracelet to add more sparkle and shine to the look.

Both of these pieces are highly versatile, and I know they’ll come in handy over and over again with party outfits in the future.

A pair of pumps would look great with this outfit, but they’re on the safe side. Instead, I wore the tortoiseshell print heel booties to keep the look modern and a little edgy, and I also like how they help balance out the volume in the sweater.

I’ve rounded up all of these plus more of my favorite holiday party pieces from Ann Taylor in the shopping widgets below.

tunic sweater // leggings // skirt // booties // clutch // earrings // bracelet // coat

photo credit: Alison Cornell

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More Classic Holiday Party Pieces:

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18 thoughts on “Holiday Party Dressing with Ann Taylor

  1. Very pretty, festive holiday outfits. I am wondering if you could style the Nordstrom Leith Body Con dress (long sleeve). I recently purchased the black one and just curious what ideas you might have for the holiday season and beyond.

  2. Wow, those booties are to die for! They are so unique yet still versatile and classic. Love.
    And it’s fun to see you venture into the faux leather leggings! They look fabulous on you and I’m loving the all black look. I bought the Spanx ones during the anniversary sale and plan to wear them just like this to one of my events this month.

  3. I like the pencil skirt and turtleneck outfit (totally what I’d wear). Are you wearing white sheer tights? 

    1. I am not wearing any tights. My legs are pretty white… I even mentioned it to Alison that day. I would have put on some self tanner had I thought about it. I had put several layers of self tanner on before we shot the cocktail dress pictures. Also, the light was bright that day, and I think she blew out the pictures when she developed them. I noticed my face was ghostly white in some pictures (I didn’t use the worst ones.) So between the lighting, the photo editing, and my pale winter legs… it does look like sheer white tights. ☺️

      1. As a girl with pale white skin I can relate! I have to use self tanner pretty much year round if I want to wear skirts or dresses. 😧😄 (It’s the English/Irish in me!) You look great – I really just thought you were wearing sheer tights because of the cold weather. I wish tights would come back in style like everything else from the 90s has!! 

  4. Love all the pieces you’re styling today. Just a question about wearing the booties with the skirt. I often see advice to go for looks that ‘elongate the leg’ in the fashion world. In my humble opinion, wearing booties with skirts, unless tights are the same color as the booties, breaks that rule. What do you think?

    1. I’ve had to get used to the look of booties with skirts. It definitely chops it up — and you could wear black tights with this, but it would give it a whole different look. I don’t have the official stylists answer to your question, but it’s a good one. I think it works, but I can’t explain why. ☺️ Maybe someone else has some insight.

  5. Hi Jolynnne! I’m a huge fan of yours but haven’t responded before this! Love your style! Can a 65 year old wear the faux leather pants? I’m in pretty good shape! Please help! Ordered a pair! Am I trying too hard!

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