This holiday season, I am excited to report that we have a number of Holiday events that we’re invited to.  The problem is that since the pandemic, I recycled most of my festive clothes.  So, this year, I am looking to put together some easy, chic, comfortable and affordable holiday outfits. Is that too much to ask? Let’s find out.

Holiday’s Gone By

Photo of a your girl dressed up for her Grandmother's holiday party.
10-ish-year-old me at one of my Grandmother’s holiday parties.

My love of holiday parties started young with my Grandmother’s (mostly) annual Christmas cocktail party. And, holiday parties used to be a fairly big part of the season for us – both hosting and those highly coveted invitations (where we’d literally be thrilled when the invitation arrived in the mail!). 

My holiday fashion philosophy has been that, no matter what time of year, if you see something you think could work and it’s a great price…get it! So, throughout the year, I would pick up things that might work for the holidays – velvet pants, gold brocaid pants, faux fur jackets and sequin tops, etc.  Then the pandemic brought all gatherings to an abrupt end –and I culled through my festive collection and now need to rebuild a bit.  

The Holiday Outfit “Brief”

I have a couple parties, a work gathering and a cocktail party after the board meeting for the non-profit that I’m on the board of.  So, I have a few different occasions, none are too dressy, but still festive.  Here is my brief:

  • Don’t want to spend a lot of money (but willing to invest in the right pieces)
  • Must be comfortable
  • Must be warm (it’s December in Chicago after all)
  • Must incorporate existing wardrobe pieces.

I think those are the parameters.  I should also say that as you’ve probably noticed, I don’t do a lot of skirts/dresses, especially in the winter.  So, while I’m loving the long satin skirts, I’m going to exclude bare legs from this holiday season.

My vision to incorporate existing things in my wardrobe, has me mostly looking for festive tops.  And, a pair of shoes that can easily transform jeans and pants into a festive outfit.  Now, let’s go shopping.

Anthropologie

My first stop for holiday outfit ideas is Anthropologie.  They consistently have fun, festive holiday attire.  I’m just looking for 1-2 pieces that I can wear with what I currently own, but I’m open to trying on lots of things.

While I tried on some very cool Pilcro jeans. Even though they were all at a great price point (around $160), I didn’t think I’d get enough use out of them, so didn’t purchase them. I have linked them in the photos below.

I also picked up this silver Dolche Vita clutch in the sale room. Something about this bag instantly elevates each outfit, making it feel more special and dressy.

Then, on a whim, I tried on this pair of silver coated jeans with a slight barrel silouette (I guess I really am “All In” on barrel jeans) and they were too cute. They came home with me.

Woman trying on a green sequin top and sequin jeans for affordable holiday outfits.
The Pilcro Sequin High-Rise Wide Leg Skater Jean
Women trying on a green sequin top and jeweled jeans for a holiday outfit.
The Austyn High Rise Wide Leg Jeans (with jewels at the pocket and studds down the leg seams).
Woman trying on silver coated jeans as she trys to put together affordable holiday outfits.
The Arin Mid-Rise Button Front, Coated Edition. These came home with me!

I picked up the green sequin sweater and did not look at the price tag before putting it on.  Not advisable!!  The minute it slid over my head, I fell in LOVE!!  It’s cashmere and SO comfortable.  It was a little pricy at $248…but, I think it’s perfect to dress up or down. 

Zara

Another GO-TO for affordable, fashion-forward clothes is Zara.  I was envisioning a sequin jacket or faux-feather jacket that I could pair with jeans or black slacks.  As predicted, they did have some, but they were a little bigger and more bulky that I was looking for.

Woman trying on a grey fuzzy Zara faux fur jacket.
Faux Fur Short Coat
Woman trying on a cream fuzzy faux fur jacket.
ZW Collection Faux Fur Jacket. It’s cute, but giving
“Polar Bear” on me.

I did find some very cute kitten heel pumps.  The kitten heel trend has been out for a while, and I haven’t tried it mainly because I do not do foot pain anymore (as I wrote about in this post).  But I was willing to try these – at $49, the price point was perfect, and they felt pretty comfortable in the store. Once at home, I adjusted the strap and they are comfortable. The toe-bed is wide enough that they don’t squeeze your toes, even though they are pointy.

Woman trying on burgundy and gold kitten heel pumps to accompany her affordable holiday outfits.
Kitten Heel Sling Backs in burgundy and metallic gold.

Banana Republic

“Banana” consistently has great clothes.  In my Fall Wardrobe Refresh, I purchased a great burgundy cashmere sweater (which could work as a holiday top). 

On this trip I found that their Holiday collection was mainly dresses and skirts – which I wasn’t looking for.  But, I did find another cashmere sweater.  I loved the rich, fuzziness of this one that made it more festive than your average sweater. 

Woman trying on a cream-colored brushed cashmere flare sleeve sweater.
It was love-at-first-touch
with this Brushed Cashmere Flare Sleeve sweater from Banana Republic.

Shop My Closet

This excercise was always dependant on pulling existing items from my closet. I planned to wear the black pants from COS that were part of the Fall Wardrobe Refresh and I also found a great Theory cream silk blouse that is about a decade old. But that’s really it. Unfortunately I have gotten rid of a lot over the years. Let’s work with what we have — and put together some festive outfits for different holiday scenarios.

Let’s Put Together some Festive Outfits

Holiday Work Event

At this time of year there are a ton of work holiday events. And, each one presents unique style challenges. For myself, I always want to dress like I’m acknowleging the specialness of the season and event, while, being appropriately dressed for a full work day. If you don’t have to travel to the event, a quick change of shoes and jewelry can do the trick.

Woman in black pants and the cream brushed cashmere sweater.
Woman in a green sequin sweater with black pants and gold kitten heel pumps.

Casual Yet Elegant

This type of event offers a lot of latitude to dress it all the way up — or be casual with just a touch of specialness. And, somehow just holding the silver clutch transforms the outfit.

Woman putting together an affordable holiday outfit in flare jeans and a green sequin top
These jeans are Lovervet by Flying Monkey The tags are still on and I forgot I had them — but having found them, I love them.
Woman in flare jeans, kitten heel pumps and a cream silk blouse.
This Theory silk blouse is from multiple seasons past, and has side zippers which make a slight peplum shape. This one is similar, unfortunately without the zipper detail.
Woman in barrel jeans, brushed cashmere sweater and boots as an affordable holiday outfit.
Dressing up the Free People barrel jeans and boots.

Don’t Forget Jewelry and Accessories

The holiday season is all about bling — so pile it on! Don’t worry about overdoing it. It’s the one time a year when “more is more” is okay. So, have fun with it. Wear the bigger hoops, the multiple bracelets and the rinestones. Add a fun bag or clutch and you have a party outfit!

Let’s be Merry!!

I feel like all these outfits will cover the invites I have this holiday. And they check all the boxes of being chic, comfortable and affordable holiday outfits. However, if we were invited to a super swanky, more formal event I would definately have more work to do. In that case, I may invest in a sequin maxi dress, a silk skirt or these silky black pants with feathers at the cuffs that I spotted at Zara.

Wishing you joy and cheer this holiday season.

WETSU! WETSU!

XO JT

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