The Ultimate Holiday Dress Guide

Those of you who have been following this blog, probably already know I am 100 percent a dress girl! In my opinion, they’re the next best thing to pajamas — classy and comfy. In fact, my mom tells me I used to cry any time she tried to put me in pants as a kid. Funny how little has changed! My closet is 95 percent dresses and skirts, which means I have plenty of experience selecting fun and flattering dress silhouettes. Whether you’re a dress lover like me, or simply have a party to attend, this holiday dress guide is sure to help you shine this season!

I’ll start with the looks I’ve selected for the holidays, then we’ll cover additional options at various price points and degrees of formality.

What makes a dress “holiday”?

To begin, let’s talk about what gives a dress its “holiday” feel. We often think of holiday attire rather literally. Yes, reds and greens reign supreme. However, selecting the ultimate holiday dress is really about texture, fabrication, a feeling of luxury, and injecting festivity into your style. A holiday dress can be any color, as long as it has that touch of “extra” glamour.

Look for satin, sequins, lace, velvet — But remember, the most important thing is finding a garment that puts that genuine smile on your face.

Satin Midi (Also in Wine) | Bow Pumps | Tassel Bag (Just $22 – Converts to Crossbody)

Additionally, when you’re looking for a great holiday dress, consider that trendy typically takes a backseat to classic, comfortable silhouettes. After all, what’s a party if you can’t move freely in your outfit? Have fun with the details, but always keep an eye out for pieces with timeless elegance. Here’s a look back at my picks last Christmas.

Holiday Dress Guide – Satin Dreams…

In 2019, it’s all about satin! For instance, this dreamy confection feels simply delicious on your skin. There’s something about satin that seems to offer royal vibes. Furthermore, the shape — featuring shirred cuffs and a shirred waistline — is universally flattering. I guarantee you’ll feel taller, slimmer, and more elegant wearing this number. The covered buttons and silhouette are reminiscent of a vintage piece, and it truly has the twirl-factor. The movement of the fabric is nothing short of exquisite.

Satin Midi (Also in Wine) | Bow Pumps | Tassel Bag (Just $22 – Converts to Crossbody)

It’s from Chicwish and on sale for under $60 (free shipping). The dress is a midi length, faux wrap style. It has a secondary lining and the covered buttons are functional. They take a bit of time, but really help make this a stand-out piece, as does the pleating at the shoulder.

Sizing notes: Chicwish has a pretty comprehensive sizing guide, just keep scrolling down until you hit the “details” section to the right of the dress photo. There you will find product length, shoulder, and sleeve measurements. Chicwish also notes the size its models have on. Read this area carefully and you should have no sizing issues.

Because this dress has such a gorgeous hue, I wanted accessories that wouldn’t compete. Consequently, I paired it with champagne colored extras — my favorite Betsey Johnson bow pumps (I’ve worn these every holiday season for the last 4 years) and a statement tassel bag. A coat with a touch of faux fur caps off the look, injecting one last touch of glam.

Holiday Dress Guide – Yes, You Can Wear Black…

Copenhagen Coat | Danika Dress | Bow Pumps (only $32!)

Let’s debunk the color myth for a second… You don’t have to wear red or green to be festive!

My second look is ideal for New Year’s Eve, but you could also wear this to a work Christmas/holiday party. The contrast of the ponte fabric with the faux leather is just enough to elevate this look from dreary to cheery. Pair it with bright red shoes and a festive earring, or opt for a statement coat in an unexpected shade like I did.

The coat is the “Copenhagen” from Peach’s Nordic Lights collection. And it really doesn’t get much cozier than this teddy bear texture! The coat beauty pairs well with jeans, but is also darling over Peach’s Danika Dress (at left) for party season. The softness offsets the edge of the faux leather beautifully.

For those new to Peach, this is a company focused on “elevated” athleisure. As a result, all of its pieces are exceptionally comfortable and offer a high degree of stretch and movement. They sent me a few pieces to style for you and I have been really impressed (more on that in this post). The price point is slightly higher than most of the clothing I share, but worth it due to the high quality of the fabrics and construction.

Need More Inspiration?

Splurge-Worthy Holiday Classics

First up, splurge-worthy holiday classics. These are the higher-end pieces I would surely pounce on if I had a really special occasion to dress up for. They are $150-$200, aside from a Ted Baker that is so beautiful I couldn’t leave it off the list.

Amazon Finds Under $40

For my fellow bargain hunters, here are a few of my favorite Amazon options for the holidays. All of these dresses have stand-out detailing, but won’t break the bank. If you try these, remember Amazon fashion tends to run small and is rarely lined. Read sizing guides very carefully and don’t rely upon the general Amazon fit guide. These pieces all have their own (more accurate) sizing guides.

Festive Formal Finds

Need something black tie? I have found some amazing pieces for you! I have always wanted to go to a fancy-schmancy holiday party, but with a toddler it’s just not in the cards… so allow me to live vicariously through you. Some of these exquisite pieces are just $50!

Happy Holiday Dress Season My Friends!