Glam Day-to-Night Holiday Outfit Ideas

1. Everyday grunge

First up, I am styling an insanely cozy striped sweater with a pair of khaki cargo pants that I splattered with black paint.

For footwear, I’m wearing a pair of Dr Martens, which add an edgy, grungy vibe.

2. Workwear silk pants

For the work pants, I’ve styled the sweater with a pair of silk pants that swish about as you walk.

I tucked the sweater of my bra so that I can show the waistband of the pants without messing with it by tucking the sweater in.

Finishing off the look are a pair of heels and a faux leather blazer. I pinned the collar of the sweater to turn it into a turtleneck look with a keyhole cutout.

3. Lunch party leather skirt

For a lunch party, I threw my hair up and put on some tights and a black leather skirt.

I tucked the sweater in to give me the right proportions and added a studded belt.

For footwear, we have a pair of shiny black boots, and to accessorize, I added some sparkly hoop earrings. A red bag adds a little pop of color.

4. Night party silk skirt

I’m wearing red lips for all of my night-time holiday looks.

Here, I’m wearing a silk midi skirt, and I added a sparkly silver brooch to the turtleneck.

I again tucked the sweater into my bra and switched out the strap on my red bag for a silver one instead.

I’ve officially transformed this cozy sweater into something that works for a fancy holiday party.

5. Casual printed t-shirt

The challenge here is that these pants inherently feel a little bit fancier, so I have to make them more casual.

I’ve gone with a thrifted printed T-shirt, a leather jacket, and a pair of Converse sneakers.

6. Silk shirt for work

Here, I’ve gone for a white silk shirt tucked into the pants, styled with a belt and my hair tied up.

Over the top, I’m wearing a black jacket and have the ends of my sleeves poking out.

7. Lunch party camisole

In this look, I’m wearing a silk camisole that I’ve tied in the center to create a really pretty drape.

To accessorize, I have a black bag with a thick gold chain that ties in nicely with the color of the skirt.

You can add even more accessories to make this neutral outfit more festive.

8. Night-time sequins

Here, I’ve paired the fantastic swishy pants with a clear belt that has a silver buckle.

On top, I’m wearing a sequined top that I just can’t get enough of - this outfit looks fabulous!

9. Casual silk

Here, I’m wearing a silk dress, but to make it appropriate for every day, I’ve turned it into a skirt by placing a silk sweater over the top.

I finished off the look with lavender sneakers, a beanie hat, and a denim jacket.

10. Workwear chic

To make the dress into a workwear look, I’m again turning it into a skirt, this time with the striped sweater from before.

I added some elastic around my waist and then tucked the sweater under it.

11. Holiday lunch party

The dress itself would be too fancy for daytime, but when you throw a sweater over it, even though the sweater is sequined, it still isn't as fancy.

12. Evening party

To make the dress evening-ready, I’ve added red lips, some silver jewelry, and then my clear heels - that’s all I need!

This would also look great for New Year's Eve.

As well as turning the dress into a skirt, you can also turn it into a top by adding a sequined skirt over the bottom of it.

Holiday outfit ideas

Think outside the box with every piece that you own. Challenge each and every piece to do double duty to really work for you, and your closet will triple in size!

I hope this gave you some good inspiration. If so, leave a comment.

Next, learn How to DIY 12 Cute and Easy Christmas Hair Accessories.