what to wear with long maxi and midi skirts

20 Looks: How to Wear Long Midi + Maxi Skirts All Year

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Post updated 6/24/23

Longer skirts can be a great look and a wardrobe staple. The best part about wearing a long maxi or midi skirt is that they’re comfortable as heck! And you can wear them in warmer weather or cold weather, on casual days, and for formal events or special occasions. 

Long skirts are a little “extra” and make the day feel special. 

But when you bring one home from the store, you may feel stumped when you try to put together long skirt outfits that look right on your body. 

I have been there! I returned several long skirts because I couldn’t figure out how to make them work. But now I have several that I love and I’m here to share with you everything I’ve discovered about how to select long skirts that work for your body type. And also how to make a whole slew of outfits you’ll feel great wearing. 

You don’t have to be tall and slender to wear a long midi or maxi skirt. I have an average-sized triangular body shape. I’m 5’6”, 165 pounds, 36-B bust, and a size 12 on the bottom. 

Before we get to the outfits, let’s talk about the best skirt styles by body type. 

Best long skirt styles by body type

If you’re really feeling stuck about how to find a skirt that you feel great in, thinking about your body type can give you an idea about the types of pieces to look for to feel confident. 

As I share this information, take the advice resonates and release the rest. You create a great sense of personal style by adding your own styling twists to outfits. A great look comes as much from breaking the styling rules as it does from following them.  After all, this blog is called Be So You for a reason.

If you’re not familiar with body types and need help figuring out your type read, How to Look Good in Your Clothes by Dressing for Your Body Type

For the triangle body type, which is larger on the bottom than on the top, the drape of a long skirt can elongate the look of your body. Reach for simple long skirts without any details like tiers or ruffles. Cargo or utility skirts with pockets placed on the hips or thighs will add bulk and draw attention to the spot they’re placed. As a triangle myself, pleated skirts also add bulk. 

For the round body type with similar measurements of shoulders, bust, waist, and hips, long skirts can create a wonderfully elongating look. Create a column of one color by pairing a long maxi skirt with a similar color top. Button-up midi skirts are another great option. The buttons up the front draw the eye up and down. Like the triangle, stick to simple long skirts without tiers, ruffles, patch pockets, or pleats. 

The hourglass body type with proportional shoulders and hips, and a defined waistline will love how a bias-cut silk midi-length slip skirt hugs your curves. Jersey knit skirts that hug your body and pleated skirts are also a great look. Add belts to emphasize your waistline.

As a rectangular body type with proportional shoulders, waist, and hips, there are so many skirt styles that can look great on you. They create shape and add volume to your lower half. Look for bias-cut slip skirts to box pleats and accordion pleats to skirts with ruffles, or ruching. 

For the inverted triangle body type with shoulders that measure larger than your hips, skirts are a great way to create balance with your upper half. Choose styles with details like pleats, ruffles, tiers, patterns, and pops of color. High-waisted styles, high-low skirts, and bias-cut slip skirts are worth a try. Belted paper bag styles add dimension to your hips to create balance with your upper body.

How to wear long skirts if you’re petite

If you’re petite and 5’4” or under, look for long skirts in the petite section because the overall sizing will work better for you. 

Look for slimmer-fitting long skirts that don’t add bulk down bottom. 

Wearing a nude pointed-toe 2 to 3-inch heel that shows a little toe cleavage or a wedge is a great way to make your legs look longer. 

Another great option is to wear a high heel boot that matches the color of the skirt to create a long seamless line. 

What shoes are best with long skirts?

There are so many options for shoes to wear with long skirts. For a casual look, go for leather flip-flops, flat sandals, or slides. For an elevated look, wear strappy sandals or wedges with heels. For colder months, try flat and heeled ankle boots or a tall boot that matches the color of your skirt for a beautiful leg-lengthening silhouette. 

How can I wear a long skirt without looking frumpy? 

The easiest way to keep from looking frumpy in your long skirt outfit is to wear a fitted top that’s tucked in and shows your waistline, acting as a counterbalance to the volume of fabric on the bottom. You also can draw the eye to your waistline by pushing up the sleeves of your shirt. 

What tops to wear for long skirts?

You may be wondering what kind of tops to wear with your long skirts.  

The easiest top to wear with your long skirt is a fitted top tucked in. On warm days, wear a tank top or T-shirt. On cold days, try a fitted long-sleeve top. A short sweater or a sweatshirt work too for a laid-back look. Wear a blazer for work. Or a leather or denim jacket for a night out. 

Wearing a maxi or midi skirt with a tank top is one of my favorite ways to style it. Tank tops highlight one of my favorite body parts, my shoulders. 

It’s easy to focus on the parts of your body you don’t like. And to label them “problem areas”. Especially if you’re having a hard time finding clothes that fit your body. I get it and I have been there. Once I found jeans that fit my bottom half, I had a turning point and it was easier to see the parts of my body that I like. 

For me, it’s my shoulders, wrists, and ankles. Sleeveless tops, bracelets, and ankle wrap shoes help to play them up. 

Have you thought about your favorite parts of your body? How can you show them off? 

Okay, switching gears from what’s fabulous about you, let’s look at some outfit combinations with long skirts.

First, let’s look at how to wear maxi skirt outfits. Then let’s look at midi skirt outfits. 

How to wear long maxi skirts

A maxi skirt hits at the ankle or slightly below the ankle at ground level. They can pool on the ground or cling all around. For this post, I’m wearing one of the best maxi skirts! It’s a straight, slim-fitting colorful floral maxi skirt from Nordstrom Rack. This high-waisted skirt has a subtle center front pleat at the hemline for some added visual interest. The waist has a flat front with a gathered elastic waistband in the back. It’s so fun to style and wear!

With a fitted white top, tucked in

One of the first long skirt outfits to try is with a fitted white shirt, tucked in. Fitted tops balance the flowy length and volume of the skirt. You probably have a few white tops you can try. Start with a T-shirt or plain tank top. You can do a bodysuit if you find them comfortable. For a high-waisted skirt, you can also experiment with a longer crop top that dips down above the high waist. Don’t worry, with the right top, your midsection won’t even show. 

White tank top and maxi skirt outfit idea

Tank | Similar Skirt Style | Slides

For shoes, you have so many options. I lean towards flat or block heels because I’m team comfort all the way. Here, I’m wearing a raffia slide with a metal buckle detail. They are comfortable but elevated by the metal buckle. You can absolutely wear flat sandals with your long skirt!

With a denim jacket

Here’s a classic combination. A denim jacket is a great way to add an extra layer and easily cover up and stay warm when the air conditioning is blasting. Choose a shorter denim jacket that stops at or above the hips to define the waistline. And roll up the sleeves on your denim jacket for the same reason. 

denim jacket and maxi skirt outfit idea

Tank | Similar Skirt Style | Slides | Bag | Jacket

This time I’m wearing a pair of knotted slides. 

With a slim-fit V-neck cardigan sweater

Here’s a fun outfit pairing a striped sweater and this floral patterned skirt. On top, I’m wearing a fitted cream and blue striped cardigan sweater. I’m wearing it buttoned up as a top. Leave some of the bottom buttons undone to help cinch the waistline of the sweater. Push up the sweater sleeves to define the waistline.

cardigan sweater and maxi skirt outfit idea

Similar Sweater | Similar Skirt Style | Slides in “Midnight”

Midnight-colored block heel slides draw in the blue of the sweater. If pairing stripes and floral prints together feels risky, make sure the stripes draw in a dominant color on the skirt. You’ll notice I’m also matching my shoes to the stripe so the stripe feels grounded and intentional. 

With a short slim-fit V-neck cardigan sweater

Wearing a slim-fitting short cardigan sweater with a high-waisted skirt gives you the perfect proportions to just leave the cropped sweater out over the top of the skirt.

cardigan sweater and maxi skirt outfit idea

Sweater | Similar Skirt Style | Slides

When cropped cardigans started showing in the stores, I wondered when the heck we would wear them. Well, turns out they are the perfect length with very high-waisted bottoms. 

With a denim shirt

Because long skirts have so much volume, you may wonder if you can wear a looser shirt with them. I love how wearing a button-up shirt adds structure up top that counterbalances the flowy bottom. And this blue denim color just happens to pick up the blue in the skirt perfectly. 

denim shirt and maxi skirt outfit idea

Shirt | Similar Skirt Style | Slides | Bag

With a sweatshirt

If you want to embrace a laid-back comfy look both above and below the waist, this outfit does that. This is a short gray sweatshirt. I used a hack I saw on Pinterest to shorten a sweater or top by tucking it up into the underside of my bra. Tuck it in front from left to right and leave it out in the back. It hits my high hip and is the perfect length to create a waistline.

sweatshirt and maxi skirt outfit idea

Sweatshirt | Similar Skirt Style | Similar Flip Flops

Pushing up the sleeves is a must to draw your eye to the waistline. 

With a graphic T-shirt

This “Le Weekend” T-shirt is a fun statement tee to pair with this lively skirt.

graphic tee and maxi skirt outfit idea

Tee (old) | Similar Skirt Style | Similar Flip Flops | Bag

Leather flip-flops are the perfect laid-back shoes to wear with them.

With a white blazer and slides

Here’s one of the best ways to wear your maxi skirt to work in the summer months. Layer your white blazer over top of a white tank top.

white blazer and maxi skirt outfit idea

Tank | Similar Skirt Style | Blazer | Slides

Wear slides or flesh-toned pointy-toe flats and you have a look for the office. 

How to wear midi skirts

A midi skirt hits a few inches below either the knees or calf, revealing several inches of skin above the ankle. In these looks, I’m showing you 3 different midi slip skirts. 

With a black tank top for a monochromatic look

This black slip skirt is another Nordstrom Rack find. It hides lumps and bumps better than the gray skirt you’ll see below.

black tank top and black maxi skirt outfit idea

Tank | Skirt | Slides

A black tank top and black slip skirt create an easy date night look for warmer weather. 

As long as we’re looking at black monochromatic looks, let’s look at two more that are very different. One is for more formal events and one is for the cooler months.

With a double-breasted blazer

Throw a black double-breasted blazer over top of your black slip skirt and black tank top for a look you could wear to an evening out.

black blazer and black slip skirt outfit idea

Tank | Skirt | Slides | Bag | Blazer

For shoes, try block heels for a more casual look, or strappy black sandals or pointy-toe heels for a more elevated look. For a more edgy look, swap out the blazer for a leather jacket. 

With a V-neck cardigan sweater

Your slip skirt doesn’t have to just be worn in the warmer months. Wear your slip skirt in the fall or winter with a pair of knee-high boots. Here I’m combining brown boots and a bag with black for a striking color combination. They appear more orange in the picture than they actually are. 

black V-neck cardigan and black slip skirt outfit idea

Similar Sweater | Skirt | Similar Bag

Button up the cardigan V-neck and wear it like a shirt. It’s hard to see here, but I left the bottom button open and tucked the front of the sweater under to create the appearance of a front tuck. 

Let’s look at another outfit for cooler weather. 

With a short sweater

I had no idea how much use I would get out of this short cable-knit sweater when I bought it. But it’s the perfect length to wear with a midi skirt like this. You can easily leave it untucked and it hits right at the top of the hips.

Short sweater and black slip skirt outfit idea

Skirt | Similar Bag

It looks rich paired with the brown bag and boots. 

With a white tank top

Here’s a more casual look with a plain tank top. Any white top will do. One that’s fitted is a great option for an easy look.

tank top and slip skirt outfit idea

Tank | Skirt | Similar Bag | Slides

You may have noticed that I’m a fan of pairing brown shoes and a brown bag with black. They’re a great choice with black for an unexpected and eye-catching color combination. 

With a flutter sleeve top

Here’s another color combination that’s spot on. I love olive with black. And this flutter sleeve tee is a bit looser than the other tops. I tucked it in and then pulled it out ever so slightly.

flutter sleeve top and black slip skirt outfit idea

Shirt | Skirt | Similar Bag | Slides

Brown accessories for the win!

With a gray sweatshirt

Here’s a gray sweatshirt with this greige slip skirt for a one-tone look that’s laid back and cool. 

sweatshirt and slip skirt outfit idea

Sweatshirt | Skirt in “Grey” | Slides

This look shows that there are so many different ways to style a long skirt!

With a graphic T-shirt

I always love the extra dose of personality that a graphic tee adds to a look. See how this black and white “J’Adore Paris” shirt creates a chic look that’s also fun.

graphic tee and slip skirt outfit idea

Tee | Skirt | Similar Slides | Bag

In the summer months, I love to pull out my graphic t-shirts. 

With a graphic T-shirt

A graphic tee can also work with a printed skirt. This midi skirt is an olive green animal print. The white tee with black writing creates a great look that adds a pop of black that looks fantastic with brown accessories. 

graphic tee and slip skirt outfit idea

Tee | Slides | Similar Bag | Similar Skirt

This would be so cute for an afternoon of wine tasting where you want to wear an elastic waistband and be comfortable and look cool. 

With a gray tank top

Here’s another unique look of a gray tank top with this gray slip skirt that has a laid-back ethereal quality to it thanks to the misty colors.

gray tank top and gray slip skirt outfit idea

Tank Top | Skirt in “Grey” | Slides

Raffia slides with a metal buckle and a bone-colored bag finishes the look. 

With a white button-down shirt

A white button-down shirt is a classic that’s also having a popular moment right now. Tuck it in, unbutton a couple of the top buttons, and roll up the sleeves for a tailored but laid-back look.  

button-down shirt and animal print slip skirt outfit idea

Similar Skirt | Shirt | Slides

Wearing an oversized white button-down shirt with a flowy bottom is a styling trick that intentionally creates visual interest by pairing two unexpected pieces together. 

An iconic moment of pairing a white blouse with a skirt came at the 1998 Oscars when actress Sharon Stone wore a crisp white button-down shirt from the Gap with a long satin lavender Vera Wang skirt. Everyone went wild for that unexpected combination. 

With a Dolman shirt and slides

A white Dolman shirt is a great structured shirt that works in warmer weather when you don’t want to wear a long sleeve white button-down shirt.

dolman shirt and animal print slip skirt outfit idea

Slides | Bag | Similar Skirt | Dolman Sleeve Blouse | Bag

Brown slides are so easy to wear!

There are so many different ways to style long skirts and make midi and maxi skirt outfits! Try classic expected combinations by tucking in a white top and topping it with a jean jacket. Or go less traditional with looser tops and sweatshirts. And push up your sleeves to draw attention to your waistline. Make layered looks with a tank top and blazer.

Have fun with it and play up the parts of your body that you love!

XO, Marya

Infographic Midi Skirt Outfit Ideas

Hi, Friend. I'm Marya. I'm so glad you're here!

I’m here to help women feel good inside and out through approachable everyday style inspiration and encouragement for midlife. Once upon a time, I worked as a therapist and coach. Now, I’m a holistic style blogger studying style coaching! Be So You celebrates leaning into who we were meant to be! 

Read about my  journey to self-discovery at 40. Follow me on Instagram here and Pinterest here. Send me a quick question through my contact page here.  

Fit Note: I’m midsized at 5’6″, 160 pounds, with size 12 jeans.

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