1 Cocktail Dress, 15 Cocktail Dress Outfits: Festive Styling Tutorial

Cocktail dresses are a key piece to own for fun parties, events, and formal nights out, especially around the holiday season. Here, I’m going to show you 15 cocktail dress outfits to demonstrate how you can make your cocktail dress more versatile and work in different ways.

Classic cocktail dress outfit

1. Classic and chic

Let’s start off with this classic look. I paired my cocktail dress with some dangle statement earrings and a pair of open-toe heels. This could work for the day or the evening.

How to style a cocktail dress

2. A touch of edge

This time, I accessorized differently. I added a printed belt and a black clutch, put on some killer black heels, and let my hair down. Now this is a definitely an evening look.

How to wear a cocktail dress casually

3. Casual and sophisticated

If you want to go easy on your outfit and show off a more laid-back look, then this is perfect! Add a black scarf and a pair of ballet flats, and you’re all good to go! 

Christmas party dress outfits

4. Backwards with a pop

Next, I decided to wear my cocktail dress backward for a different shape. Now, the front neckline is high and the back has a dip, which is really lovely. I also added a pop of red with the bag and shoes - very festive!

How to style a cocktail dress for work

5. Workwear mix

Here, I wore my favorite blazer and black heels, then matched the whole outfit with a lovely black purse. This cocktail dress outfit could work in the office or at an event; it's the perfect transition outfit for a work Christmas party.

Casual cocktail dress outfit ideas

6. Festive casual

If you want to know how to wear a cocktail dress casually, then this outfit is a definite hit! It’s really cohesive and perfect for those casual occasions. I simply tucked in my denim shirt at the waist and paired it with pointy pumps. 

Different ways to style a cocktail dress

Ok, so this one’s quite simple - I swapped my pumps and purse for red ones, and look what a difference it makes! You could carry these accessories with you if you need to be out during the day, but have an event in the evening.

How to wear a cocktail dress in winter

7. Laidback luxe

I love this cocktail dress outfit! This is another stylish, casual vibe. I wore a black cardigan, tucked the dress under the bottom part of the cardigan for a funkier look. Next, I wore a denim jacket and paired everything with my pumps. What do you think? 

How to wear a cocktail dress with boots

8. Urban casual

For those who want to know how to wear a cocktail dress with boots, then this urban outfit is just for you! I paired my cocktail dress with black ankle boots, denim jacket, and black scarf. I also went for some lovely hooped earrings and tied my hair up. 

Cocktail dress outfit with a tulle skirt

9. Ballerina inspired

Move over, Cinderella! This is the most amazing ensemble for those formal cocktail parties. I simply wore my tulle skirt over the dress, adjusted the cocktail dress’ belt, so it sits snugly over my waistline, and paired the whole outfit with strappy heels and a shiny clutch bag. 

Cocktail dress outfit with pants

10. Metallic mix

It’s time to get your metallic game on with this lovely funky mix. I’m wearing gold metallic wide-legged pants underneath my cocktail dress and paired them with my metallic clutch bag. This look is edgy, casual, yet dressy. It certainly makes a statement.

Winter cocktail dress outfit

11. Color blocked

Here, I’m wearing a mustard-colored turtleneck underneath my cocktail dress. I then paired the cocktail dress outfit with ankle boots and a neutral-colored purse. This is great for the colder winter months.

Retro 70s cocktail dress outfit

For those of you who want to go back in time, then this retro look is perfect! Keeping to the same look as above, I simply swapped my ankle boots for knee-high boots.

Cocktail dress outfit with a leather jacket

12. Edgy city style

Here’s another wintry and sultry look. I paired my cocktail dress with a black leather jacket, shiny knee-high boots, and a lovely cross-body bag. Also, I wore a black turtleneck underneath for extra warmth.

Layered cocktail dress outfit

13. Layered

For those who love layers, this is a great outfit for you. I wore a faux-fur open vest and layered it with my favorite denim jacket. This will keep you feeling cozy and warm.

Wearing a cocktail dress as an open kaftan

14. Monochrome and open

As my cocktail dress is a wrap dress, I decided to wear it like an open kaftan and wore an all-black outfit underneath. I paired this look with black heels and put my hair up in a bun for a super sleek vibe. 

Glamorous winter cocktail dress outfit

15. Winter glam

If you want to know how to wear tights with a cocktail dress, then I've got you covered. This is great for those cold wintry nights. Simply put on some sexy tights and throw in a printed jacket to the mix. Looks fab! 

Cocktail dress outfits

There you have 15 or more cocktail dress outfits that you can use to shake up yourgo-to event dress this festive season. Let me know what you think of this styling tutorial in the comments below.

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 1 comment
  • Tracy Tracy on Nov 23, 2021

    Always inspired by your ideas. I’m working with metallic/chiffon blouse, metallic tank top and suede maxi skirt. The fun part will be in accessories, as I can’t wear heels. It’s my first cocktail party in years and I’m even excited to dress up my husband—he’s a very handsome guy—and would appreciate your take on that!