33 Chic Ideas for Midi Skirt and Sweater Outfit: From Casual to Classy

There are some style formulas that just work: straight-leg jeans and a button-down shirt, a mini dress, and an oversized blazer.

Or our personal favorite, the midi skirt and sweater outfit.

These foolproof fashion formulas allow you to build a closet of wearable outfits that never go out of style.

In particular, pairing a midi skirt with a cozy sweater is the perfect transition outfit that can be worn all year round.

And did we mention it’s comfortable too?

In this article, we round up 35 of our favorite ways to wear a midi skirt and sweater outfit, including the DOs and DON’Ts of styling this classic combo.

33 Chic Combinations for Midi Skirt and Sweater Outfits

We love a versatile outfit combination, and nothing quite beats a midi skirt and sweater.

By playing around with fabrics, silhouettes, colors, accessories, and and textures, you can create totally different and unique ways to wear the same wardrobe staples over and over.

Here are 35 of our favorite outfit ideas to inspire you.

1. Double denim

Try throwing a denim shirt over a turtleneck sweater and pairing it with a matching denim midi skirt for the coolest transition look this fall.

The secret to looking chic is going for a darker denim wash, sophisticated silhouette, and pared-down accessories.

Denim Cargo Liner Jacket

2. Bright monochrome

Make a statement with a bright monochromatic midi skirt and sweater outfit. Neons and bright primary colors will create a bold look that’s both playful and strong (reds and blues are big news in 2024).

Just remember to play with textures to give your look dimensions. Neutral shoes and a matching bag will finish the look.

Catara Virgin Wool & Cashmere Coat
Bouclé Tweed Double Breasted Coat

3. Leather skirt

A lightweight sweater is the perfect way to dress down a leather midi skirt for a cool daytime look.

Pair with long boots for a casual finish, or add a pair of pointed heels to dress it up.

Patch Pocket Faux Leather Skirt

4. Textures

Experimenting with textures is a great way to elevate this classic style formula. So, why not try a textured skirt with a lighter sweater for a fun new take on a classic silhouette? 

Just remember proportions! Textured fabrics on the bottom half of the body can create unwanted bulk or draw attention to that area, so you may want to balance those proportions on the top half of your body too.

Ruched Tulip Hem Skirt

5. Graphic tee

Throwing your favorite graphic t-shirt on with a satin midi skirt and some cool sneakers can create an effortlessly chic look.

This is a great way to dress down a midi skirt for an undone daytime look.

Oversize Empire State Graphic Sweater

6. Patterned skirt

Playing around with bold patterns is always fun, but it can quickly cross the line into garish. A great way to avoid this is by sandwiching the pattern with neutrals or plain colors.

For instance, styling a boldly printed midi skirt with a neutral sweater and long boots in a matching color balances the loud pattern and creates cohesion.

Stripe Ruffle Faux Wrap Maxi Skirt

7. Cropped sweater

Teaming a midi skirt with a cropped sweater creates a really fun and flattering silhouette (provided you get the length of the sweater right).

Aim for the sweater to stop about an inch above the waistline of your midi skirt, and make sure that you don’t go for a tight sweater and skirt. As a general rule, if you opt for a tight-fitting cropped sweater, pair it with a slightly looser or more voluminous skirt to create dynamic proportions. 

Alternatively, throw an oversized blazer over the top to get the balance right.

Distressed Topstitch Rib Crop Sweater

8. Western boots

Western boots are a big trend at the minute, making them the perfect choice of footwear to freshen up your standard midi skirt and sweater outfit.

They go perfectly with a denim midi skirt and sweater or can toughen up a more delicate satin skirt.

Kacey Western Boot

9. Light colors

We love a head-to-toe monochromatic look, but sometimes it can be hard to get the color match just right.

A fun alternative is to go for similar (but not matching) colors. For instance, you could team different pastel tones or shades of blue. Keep your accessories and footwear within the same colors for a cohesive look.

Crewneck Sweater

10. Tweed skirt

Tweed midi skirts are big this year and offer an excellent way to update the classic midi skirt and sweater outfit.

Just be aware that the thicker tweed material will work best with a thinner, more loose-fitting sweater. This outfit works great with tall leather boots or a pair of loafers.

Front Slit Tweed Pencil Skirt

11. Chunky loafers and a T-shirt

The fashion holy grail, a satin midi skirt always looks chic with a tight-fitting t-shirt and some loafers.

The key is to balance proportions by going for chunky loafers and throwing over a chunky cardigan or sweater. A slim fit or cropped t-shirt and some chunky jewelry will finish the look.

Carnaby Chunky Leather Loafer

12. Vintage accessories

Vintage never goes off the style radar for too long, and it’s officially back this season. So, breathe fresh air into your usual midi skirt and sweater outfit by adding some vintage touches like headbands, jewelry, or a vintage handbag.

3-Piece Enamel Clementine Coin Necklace Set

13. Statement sleeves

Statement sleeves can create structure and turn a classic outfit into a showstopper. So, it’s the perfect way to reimagine the classic midi skirt and sweater look.

Just remember to balance big sleeves with a chunkier shoe choice to avoid looking top-heavy and to create some well-needed flow.

Aubrey Crop Cardigan

14. Pleats

Everyone should own a well-fitting pleated midi skirt. The pleats create texture and skim your body in a flattering way for a sophisticated silhouette.

A pleated skirt is also a great item because it can be dressed up with pointed stilettos or down with brogues or flats. 

Microstripe Pleated Knit Cotton Midi Skirt

15. Head-to-toe neutrals

Earthy tones and neutrals remain firm favorites in the fashion world, and it’s hardly surprising. There’s something timelessly elegant about a head-to-toe neutral outfit, especially when you combine textures for an expensive finish. Plus, neutrals are great building blocks for a chic capsule wardrobe.

For this look, team a neutral midi skirt with a sweater in a different tone or shade. Finish the look with leather boots and a suede handbag for a luxurious outfit.

Tyra Wrap Front Tulip Hem Silk Skirt

16. Oversized

Most midi skirt and sweater outfits feature a tucked in or cropped knit to create definition around the waist. However, oversized looks are set to be a huge trend in 2024.

So, why not try mixing up your usual go-to look by pairing an oversized (and untucked) knit with your favorite midi skirt. 

Go for monochrome to create length and keep things simple, and pop on a pair of high-heeled boots to dress the look up.

Stripe Oversize Organic Cotton & Wool Crewneck Sweater

17. Sporty

Sportswear has slowly infiltrated catwalks and closets alike, especially for fans of streetwear. For a new take on the midi skirt and sweater look, try swapping your standard knit for a hoodie and team it with a midi-length cargo skirt. 

Going for monocromoe or muted color palettes will create a more sophisticated feel, and this outfit looks great with your favorite sneakers. You could also add a high-heeled knee boot to dress the look up.

Sportswear 2000 Hiking Shoe

18. Floral skirt

Floral prints never stay off the runway for long, and they’re back with a vengence this season. Swapping your usual midi skirt for a floral number is a fun way to give a nod to this trend and it will see you right through to the summer.

This pairs really well with a cableknit sweater or a turtleneck.

Floral Print Pleated Midi Skirt

19. Dark academia

The dark academic aesthetic has been a huge trend, and it doesn’t look like it’s going anywhere. Channel the look by teaming a woolen, pleated midi skirt with a thick knit, brogues, and a long pea coat over the top. Dark browns, greens, greys, and navy colors work best.

Accesorize with a scarf and a leather handbag to complete the look.

Midi Skirt and Sweater Outfit
Crewneck Sweater

20. The nineties

Our obsession with nineties fashion continues, as grunge remains big this season. So, if you want to channel the nineties, try pairing a tartan midi skirt with some combat boots and a fluffy cropped sweater. 

Simply throw an oversized leather jacket and handbag to complete the look.

Balfern Studded Leather Biker Jacket

21. Low rise skirt

One trend that is receiving mixed reactions is the return of low-rise jeans and skirts. If you’re brave enough, try swapping your usual high-waisted midi skirt for a low-rise one and pair with a lightweight, loose-fitting sweater.

Faux Leather A-Line Midi Skirt

22. Metallics

Metallics (especially gold) are set to be a massive trend in 2024. For the brave, you may want to invest in a metallic gold midi skirt, but for the rest of us, some accessories will do the job.

Give a nod to this new trend by adding a metallic handbag and shoes to your midi skirt and sweater outfit.

Pleated Metallic Satin Midi Skirt

23. Belt bag

Belt bags are another big trend for next year and an excellent way to give your midi skirt and sweater combo a casual twist.

Go for a sportier midi skirt, like a cargo skirt, and pop on a belt bag for a hands-free look that’s totally on trend.

Crossbody Belt Bag

24. Bomber jacket

A great way to jazz up your usual midi skirt and sweater look is to throw a bomber jacket over the top. 

Opt for a cropped bomber with plenty of tailoring and structuring to create a cool and chic ensemble. We love this look in monochromatic colors like blue or green.

Embroidered Dragon Bomber Jacket

25. Seashell accessories

Mermaidcore is having a moment, and this is likely to continue in 2024. Think seashells and netting. If you aren’t quite ready to fully commit to a mermaid look, you can dip your toes in the water (excuse the pun) with some accessories.

Team a mid-length tube skirt with a thin sweater and some seashell earrings or a statement purse.

‘Seashell’ Pendant Necklace
Metallic Seashell Scallop Headband

26. Tulle skirt

Another key trend for Spring/Summer 2024 is ballerina-inspired looks. We’re talking tulle, powder pinks, and gowns.

You can get in on the trend early with a tulle midi skirt in a pastel pink or nude and a cableknit sweater. If you want to fully embrace your inner ballerina, try adding some ballet pumps. Alternatively, you can toughen the look up with some leather knee boots.

Wendy Beaded Tulle Skirt

27. Thin belt

Elevate a tailored midi skirt and cashmere sweater by adding a thin leather belt to define the waist. This is the perfect workwear look and can be dressed up with some heels or down with leather calf-boots.

Laque YSL Monogram Leather Belt

28. Bows

Good news for the girlie girls out there: bows are back. They’re also a pretty inexpensive way to update your classic pieces (like a mid-length skirt and sweater) and give a nod to new trends.

There are lots of ways to incorporate bows into your outfit, like by adding them to your sweater, your hair, or as a belt.

Bow Mohair Blend Cardigan

29. Black and white

Black and white is a classic color palette that never goes out of style. Try teaming a black satin midi skirt with a white cableknit sweater, chunky black loafers, and frilly white socks for a cool transitional look.

Atlas Santina Mix Media Sweater

30. Neck accessories

Pussy bows and other types of neckerchief and neckties were all over the runways, creating a bold silhouette and adding drama to pared-down wardrobe pieces.

Take inspiration and add a neckerchief to your sweater and midi skirt combination, or invest in a sweater with a pussy-bow neckline for a modern twist.

Mixed Crystal Frontal Necklace

31. Skirt over pants

Wearing a midi skirt over pants may seem crazy, but it’s big news this fall and winter. Don’t worry, though, this fashion trend has had a sophisticated glow up since the early 2000s.

This time round, try adding a pair of pants in a matching or complementary color under your midi skirt for a cohesive and cool look. 

We love plaid wide leg pants under a matching asymmetric midi skirt and a neutral sweater.

Alma Pinstripe Buckle Strap Skirt
Chamomile Oversize Cardigan

32. 1950s

The fifties was all about feminine glamor – pin-up style dresses, cinched waists, and long skirts. And we’re delighted that it’s back in style.

Get in on the action by teaming an A-line midi skirt and a cinched waist with a tight-fitting sweater to accentuate your curves. Pop a petticoat underneath for some serious volume and balance your proportions with a structured shoulder.

Masilke Rib Drawstring Midi Skirt

33. Polka dots

The polka dot is having a renaissance this year, making it the perfect time to play with pattern.

Freshen up your look by adding a polka-dot sweater or midi skirt to your closet. Or, if you’re feeling brave, go for a matching polka-dot set. A midi skirt will look more chic than a mini. 

Polka Dot Sunray Pleated Skirt

Styling A Midi Skirt and Sweater Outfit: The DOs and DON’Ts

It may be a pretty foolproof fashion formula, but there are still some things to remember if you want to get the midi skirt and sweater outfit right.

Picking the Right Midi Skirt 

With the wrong shoe, sweater, or styling choices, your midi skirt can quickly go from fashionista to old maiden. So, choosing the right skirt is a must.

Here are some tips on how to choose the right midi skirt for your body shape:

  1. Get the proportions right

Traditionally, a midi skirt should fall to your mid-calf. However, this isn’t always the most flattering length unless you were born with supermodel legs. 

That doesn’t mean you should avoid midi skirts, though. All it means is that you need to find a slightly shorter version that looks best with your proportions. As long as it sits somewhere below your knees and above your ankles, it’s considered a midi.

If you’re a whizz with a sewing machine, you can simply bring the hem up slightly so that your skirt sits at a more flattering angle for your body shape.

Similarly, getting the right shape and fit matters. For instance, if you’re a pear shape and you want to accentuate your small waist while simultaneously skimming your widest parts (hips and thighs), then an A-line midi skirt could be what you want.

Alternatively, a straighter, more fitted midi skirt is perfect if you want to show off your long legs.

  1. Choose the right footwear

As we already mentioned, your choice of shoe can make or break your midi skirt and sweater outfit. So, choose wisely.

Generally speaking, you want to avoid wearing ankle boots or ones that come to just below where your skirt falls.

This is just not a flattering look on anyone. Instead, opt for a calf boot that comes to just above where your skirt finishes.

Or go for a full-length boot. 

Western-style boots are also big this season and will balance your proportions nicely.

For a more casual, street style, pair your midi skirt with your favorite pair of sneakers and some socks.

If you want to dress your midi skirt and sweater outfit up with a pair of heels, we recommend skipping the ankle strap.

This can cut off your leg, giving the illusion that they’re shorter than they actually are.

Instead, choose a neutral sandal or a pair in the same color as your skirt to create length.

Pointed stilettos also look great with a midi skirt.

On warm, sunny days, midi skirts look great teamed with slides or flat sandals. 

Finally, channel your inner off-duty model by wearing your midi skirt with a pair of chunky loafers and some cute socks.

This will balance your proportions and look fashion-forward.

  1. Pick the right fabric

The material of your midi skirt can seriously impact the overall look of your outfit.

For example, cheap, satin materials tend to cling in all the wrong places and make it difficult to tuck a chunkier sweater into your skirt without creating lumps and bumps.

On the other hand, thick fabrics can drown smaller frames and create a frumpy look.

The key is to choose a material that flatters your body shape and is versatile enough to go with your existing wardrobe pieces.

A good-quality (and well-fitting) satin is a great choice because it can be dressed up or down for different looks.

Or, a pleated fabric works well for A-line skirts, creating movement and flattering curves.

There are plenty of options out there, so play around until you find the fabric that best suits you.

  1. Think about your outerwear

You really can’t go wrong with a midi skirt and sweater outfit, but you do need to consider how you’ll layer up in winter.

Therefore, finding the right length of coat or jacket is essential to finish off your look. 

The general rule is either long or short. In other words, either go for a cropped jacket that sits just on the waistline, or go for a full-length coat that stops just below the skirt. 

Of course, isn’t set in stone – fashion rules are made to be broken, after all.

Don’t be afraid to experiment with other silhouettes, but these two options are failsafe if you’re struggling to complete your look.

Picking the right sweater

The midi skirt and sweater outfit is a classic, but there’s an art and a science to getting it right. That means pairing the right sweater with your skirt. Here are some tips to nail it.

  1. Get the right thickness

The key is to get the balance right between the thickness of the sweater and the material of the skirt. What you really don’t want is to create a lumpy look or to get your proportions off.

Generally speaking, a sweater that’s on the thinner side is easier to style with a midi skirt.

For instance, a thin mohair sweater will look great with a thicker or more structured skirt, like a tweed or leather midi.

On the other hand, a chunkier knit will look great with more delicate skirts, such as satin.

Basically, you don’t want to pair two super thick or super thin fabrics together.

In the same vein, if your skirt is form-fitting, it’s best to opt for a looser-fitting sweater and vice versa.

  1. Think about length

Versatility is an important factor to consider, so it’s best to choose a sweater length that is most wearable with your wardrobe.

That said, a slightly shorter sweater works best when tucking it into a midi skirt because you don’t have a lot of excess fabric. 

Ideally, you should go for a sweater with a fitted hem that’s easy to tuck into your waistline without creating a bulky look.

  1. Master the tuck

The biggest fashion faux pas we see with this look is the wrong tuck.

Getting the tuck right will make sure that you accentuate your waist, remove unflattering lumps, and create an effortlessly cool look.

For thinner sweaters, you can tuck them directly into your waistline and add a belt for definition.

For chunkier knits or longer sweaters, you may want to tuck them into a bra or under top to get that perfect tuck.

Trust us, it makes all the difference.

If you’ve gone for a cropped sweater, you won’t need to tuck at all.

Just make sure the sweater falls just above the waistline of your skirt for the most flattering look.

For a really laid-back and oversized look, you could not tuck your sweater into your skirt at all.

This can look cool, but it lacks definition, so make sure you play with proportions to avoid drowning in your look. 

  1. Get the details right

One of the great things about this outfit combination is how versatile it is.

You can go for chic monochromatic looks or eclectic color blocking.

The same goes for proportions and silhouettes – the world’s your oyster.

That said, it’s worth reminding you that striking the right balance on the top and bottom half of your body is key.

For example, a sweater with statement shoulders or a lot of volume on the top will look best with a skirt that mirrors that volume on the bottom (a flare or A-line skirt).

This will balance proportions and create a cohesive look. 

Conversely, pairing a sweater with big shoulders with a tight-fitting skirt can create the illusion that you’re top-heavy or create an off-kilter look.

Finally, be mindful about where you add embellishments and details because that’s where the eye will be drawn.

In other words, stick to detailing like beading or tassels in the parts of your body that you want to accentuate.


We hope these ideas inspire you to experiment with your standard midi skirt and sweater outfit.

This classic style formula is versatile, chic, and flattering, making it a closet must-have.

Plus, by playing around with accessories, color, print, and texture, you can create fresh new looks from your wardrobe staples.

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Julie Higgins
Julie is a Staff Writer at momooze.com. She has been working in publishing houses before joining the editorial team at momooze. Julie's love and passion are topics around beauty, lifestyle, hair and nails.