Inside: 27 skirt outfit ideas for any season of the year. Because skirts are always your cutest option.

When picking out an outfit under any dress code, there’s always a skirt option. If you’re a skirt girlie, that is.

I love throwing skirts into the mix even for a more casual outing! Heading to dinner? Instead of jeans I love a good tennis skirt even with a tee. Cold weather? Throw on a pair of tights and a sweatshirt with your little black mini skirt and you’re good to go! It’s so easy but makes you look so put together.

Speaking of put together, there’s nothing that looks more like it than a dress. However, when you can pair a whole outfit together, that’s when you know you’ve really got a coordinated outfit. Piecing together outfits can be fun but challenging, especially if you have to deal with layers in some of those tricky colder months.

But here are 27 skirt outfit ideas for all occasions and seasons.

Five women in skirt outfits

Tips For Pairing Skirts

I’m a huge fan of pairing skirts and tops or pants and tops rather than just throwing on a dress, at least when I want to look like I really am making a statement.

I can’t express how cool skirts can be when you know how to play the cards with them, so here are some of my favorite and most simple tips when it comes to pairing skirts in any season.

As with pairing any pieces together, you’ll want to start with focusing on colors. Seems easy enough, and when you match colors or mix colors excellently, your outfit will already feel super put together. We already do this without thinking, if you grab a pink top, you already know in your mind which pants you can wear with it. But if you’re ready to mix it up, you could totally reach for something that goes against everything you think you know about how to pair colors. This is the year of color blocking, so we love an experimental color situation.

Next up is silhouette and length. These two kind of go together, as they lend to the same visuals when pairing your outfits, but they have some slight differences, even among the similarities.

The silhouette is the shape of the skirt and how it’s perceived. If you want a more formal look you go with a fitted silhouette, and if you want a preppy or casual look, go with an A-line skirt.

These skirts can give totally different vibes depending on the actual design, color, fabrication, et cetera, but for the most part sometimes it’s simply the silhouette of the skirt that makes a difference. If you’re wearing a blazer, the fitted skirt might be perfect for a more business look, or if that’s not what you’re going for, something looser fitting or more flared would make it a bit more relaxed.

However, this is where length comes in.

If the blazer is about the same length as the skirt, then the fitted is perfect to turn the blazer into more of a blazer-dress vibe. If it’s short and you can see a lot of the skirt, that’s where you’re going to have to be intentional with the styles.

Make sense?

Trending Skirts In 2023

The mini skirt has had its big moment lately, and it will always be a staple for summer and spring when you just need something a little cuter than your usual denim shorts.

But this year, we’re seeing a strike against the “micro-mini” that was trending so high during the Y2K resurgence.
The maxi skirt is everything these days, and you’re going to want to hop on this trend!

It’s not for everyone just yet– if you’re worried about looking homely and too modest right now if fashion isn’t huge where you live, then wait this one out but maybe have a maxi skirt waiting in your closet for its time to shine.

Pairing with the tiny crop tops or the attention grabbing faux fur that’s trending will be sure to make a statement with whatever maxi you’ve chosen for your look. It’s a cool look, if you do it right. We’ll dive into some examples of the maxi skirt done right so you know what to do when you’re staring it in the face, trying not to look like a missionary while trying to be ahead of the trends.

If this intimidates you– the mini skirt will always be a good move. She’s not over yet, so don’t get rid of your minis just because maxi is having a moment.

Best Pieces To Pair With Skirts

The easy answer to this is everything.

You will always have success pairing sweaters, tee shirts, blouses, basic tops with a cool jacket… there’s not really a right or wrong answer for what goes with a skirt.

If you want to be more edgy and on trend for this year, a couple pieces to look out for are racing jackets, velvet blazers, and as always: graphic tees. My personal favorite.

I love to balance edgy and girly as part of my personal style. But if you’re all girly, a frilly cropped blouse with dramatic sleeves are really hot right now and you can always channel something edgier with a different pair of shoes for something more subtle!

Three girls in summer outfits, all with skirts

Spring/Summer Skirt Outfit Ideas

The spring and summer seasons are the easiest to whip out a skirt in. It’s a no-brainer and it’s easy to beat the heat when there’s a breeze, even through a maxi skirt.

Here are some cute and creative outfit ideas with skirts for spring and summer.

1. Pleated Maxi
2. Army Vibes
3. Leopard Print Skirt
4. Denim Skirt
5. Floral Mini
6. Ruffles And Cottagecore

Cute and trendy winter outfits

Fall/Winter Skirt Outfit Ideas

Colder seasons don’t necessitate anything that will leave you feeling breezy. But there are ways around it. I love these winter versions of your favorite skirt outfits.

7. Sweater And Plaid
8. Color Pop
9. Leather Skirt
10. Maxi Denim
11. Studious
12. Blazer And Tights
13. Vest
14. Monochrome Sweater And Silk


We all love a good dressy skirt moment.

15. Rusty
16. Incredibly Chic
17. White Button Up
18. Edgy Gold
19. All Black
20. Taupe
21. Heels

Edgy outfits with skirts

Cool Skirt Outfits

Trendy? Edgy? Cool? Yes, please.

Here are all the trendy and cool ways to wear a skirt in 2023.

22. Slouch Boot
23. Tube Top
24. Color Pop Pumps
25. Leather Mini
26. Ultra Preppy
27. Graphic Tee

You can’t deny how cute some of these skirt outfit ideas are. When you start diving into the dynamics of how you can pair skirts with anything from sweaters, tees, tanks… There are so many options and your wardrobe opens up completely. Wearing the same top with the same jeans is easy and comfortable but every once in a while switch it out for a skirt and you’re golden.

Have fun playing around with these different skirt ideas, fashion is all about fun and pairing pieces together makes it all so much better. Playing with silhouettes, shapes, lengths, and colors makes getting dressed interesting. If you’re not a fan of figuring these things out and prefer to have someone tell you how to do it, that’s what this post is for. Simply mimic what you see here and you’re going to love what you get.

More cute stuff here!

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