How to Rock Casual Skirts in Every Season

If you’re anything like me, you’re all about staying stylish while juggling the joys of motherhood. Today, let’s dive into the world of skirts and discover the art of rocking them casually.

Whether you’re a floral prints lover, an animal print aficionado, or a tennis skirt enthusiast, we’ve got you covered.

From maxi skirts to short skirts, we’ll explore how to incorporate these wardrobe staples into your everyday wear and even pull off those formal events with a casual vibe.

Get the easy styling tips and the best casual skirt outfit formula below.

THE ULTIMATE GUIDE ON HOW TO WEAR SKIRTS CASUALLY

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How to Wear Skirts Casually

I have shared my tips on how to wear maxi skirts and a classic black pencil skirt, but have you ever wondered how would you wear a “dressier” skirt like that more casually?!

This post offers the answer to that question. No matter how “dressy” your skirt may be, you can style it with more casual tops and shoes to create an ultra stylish and functional outfit.

With life as a busy mom and entrepreneur, I am typically in more casual attire as opposed to being dressed up, so I love to style my skirts to fit my more laid back lifestyle, while still looking put together.

I would say my favorite way to style skirts is with a graphic tee or sweatshirt, and a fun pair of sneakers.

You can’t go wrong with this cute combination and the possibilities are truly endless as there are so many different variations of all of those items.

How to Wear Skirts Casually

TIPS TO FOLLOW:

1. Embrace the Floral and Animal Prints:

Floral prints and animal prints are like a breath of fresh air for any outfit.

When it comes to floral prints, opt for a midi floral skirt with a neutral-colored top for a balanced look.

Animal prints, on the other hand, can add a dash of fierceness to your ensemble.

Pair a leopard print tennis skirt with a white shirt and high heels for an effortlessly chic appearance.

2. Elevate Your Look with High Heels:

Speaking of heels, they’re not just for fancy occasions.

Pairing high heels with casual skirts like tennis skirts or even a cute mini denim skirt can instantly elevate your style game.

They add a touch of sophistication to your overall look, making you feel like a fashion maven, even when you’re just running errands.

3. Mastering the Maxi Skirt Magic:

Maxi skirts are your best friend, dear moms. They’re versatile and oh-so-comfortable.

For a casual daytime look, throw on a maxi skirt with a cute polka dot or lace top. Need an extra layer for colder months?

A black leather jacket will do the trick, giving you that relaxed yet stylish look.

4. High-Waisted Wonders:

High-waisted skirts are a godsend for moms of all body shapes.

They cinch at the narrowest part of your waist, creating a flattering silhouette.

My latest obsessions are the high waisted tennis skirts. Most have shorts built right in!

Pair a high-waisted black skirt with a white t-shirt, and you’ve got an outfit that’s perfect for warmer weather.

5. The Power of Accessories:

Accessories can make or break an outfit, so don’t underestimate their influence.

From black boots to cute sneakers, they can completely change the vibe of your look.

If you’re a fan of long denim skirts or a sheer maxi skirt, experiment with different accessories to find what suits your personal style best.

6. Transitioning Through Seasons:

Skirts are your go-to option for transitioning between seasons.

For colder months, layer a bike shorts or tights underneath your skirt. In warmer weather, opt for lightweight fabrics like a white top with a flowy maxi skirt.

7. A Timeless Classic: The Little Black Skirt:

Just like the little black dress, the little black skirt is a must-have.

Pair it with any kind of top – from a lace top to a casual white shirt – and you’ve got an outfit that’s ready for any occasion.

It’s a versatile piece that will never go out of style.

8. Embrace Your Unique Style:

Remember, fashion is all about expressing your unique style.

Mix and match different skirts with various tops to create different outfits that reflect your personality.

Don’t be afraid to step outside your comfort zone and try new combinations.

TYPES OF SKIRTS TO LOOK FOR:

These types of skirts are great for casual looks!

Mini Skirts

A mini skirt is the shortest of all of the skirt variations, with the hemline that hits about mid thigh. Mini skirts are trending right now, especially paired with taller boots that are also trending.

There are all different types of mini skirts that you can style casually such as: tennis skirts, plaid skirts, bubble skirts, a-line skirts, ruffled skirts, button down skirts, denim skirts and bodycon skirts.

Mini skirts are easy to style casually as the longer the skirt, typically the more “formal” it looks.

You can style mini skirts with casual tops, and show off your legs and a more casual style shoe such as white sneakers or over the knee boots to complete the look.

Midi Skirts

A midi skirt is a longer skit that hits anywhere from below the knee to the lower calf. 

Midi skirts have become more popular over the last few years as they are easy to style, give an effortlessly chic look and are very comfortable.

The longer length is ultra flattering on all body types and gives an elongating and lengthening effect.

Some different types of midi skirts that can style casually are pleated skirts, black pencil skirts, floral midi skirts, knit midi skirts, wrap midi skirt and a-line midi skirts.

I love to style midi skirts with ankle boots and sneakers as the length of the skirt hits at the perfect spot above the top of the shoe.

Flats are also a great option as the length of the skirt will not drag along the floor.

Maxi Skirts

Maxi skirts are skirts that stop at the ankle or at ground level.

Maxi skirts are the longest variation of all different types of skirts and truly lengthen your silhouette.

When it comes to styling long skirts casually, the attention should remain on a more casual/effortless top and shoes that offer a bit of height in order to avoid the hem of the skirt dragging along the ground.

I love the style maxi skirts with booties, knee-high boots and wedges to offer that bit of extra height.

Tops to Wear with Skirts for a Casual Look

Tops to Wear with Skirts for a Casual Look

Basic Top:

A go to tank top or crisp white tee is such a simple option to style a skirt more casually. If it is more fitted, you can tuck the top into your skirt, or if it is flowy you can knot it at the waist to create a chic crop top type of fit.

Denim shirt:

A denim shirt is a classic casual option, as denim itself lends a more laid back feel. A button down denim shirt would look so cute paired with a pleated skirt or a floral midi skirt. You could tuck it in, or tie it in a knot.

Graphic tee:

My favorite casual top to style with skirts is a graphic tee! No matter what type of skirt, when paired with a graphic tee it instantly gives the look a more casual feel and is so comfortable too! I love a graphic tee paired with a faux leather skirt, a denim skirt, or a pleated maxi skirt. The options are truly endless, and I love to match the colors in the graphic tee to the color of my skirt.

Oversized sweater:

For the cooler months, and oversized cozy sweater is another great casual top option to pair with skirts. You can tuck it in, knot it, leave it oversized, etc. I love a flowy top with a more fitted skirt, and paired with knee-high boots or sneakers this is a chic look that is perfect for Fall.

Added Layers:

My go-to layers for casual outfits are a classic denim jacket, a suede moto jacket, a black faux leather jacket, a cozy cardigan and an oversized flannel shirt.

Shoes to Wear with Skirts for a Casual Look

Shoes to Wear with Skirts for a Casual Look

Ankle boots:

Ankle booties are my favorite casual boot to wear, as they are just as functional as they are stylish.

The slight added height they offer is so flattering, and the ankle height really pairs well with all types of skirts.

As you can see in the photo above, the nude colored ankle boot is ultra flattering with the above ankle length of my pleated skirt. Paired with a cute graphic sweatshirt, this is a perfect casual outfit.

Here are some affordable ankle booties that would work great when paired with skirts casually:

Sneakers:

The ULTIMATE casual shoe = SNEAKERS! I am always looking for new ways to style sneakers that is chic and stylish, and pairing them with unexpected items such as skirts is really trendy.

Not only are they the most comfortable option, but they also are really versatile when it comes to styling as there are so many different options to choose from.

You can’t go wrong with classic white sneakers, or fun flat sneakers such as Golden Goose or Converse!

Here are some cute sneakers that I think pair really well with all different skirts to create a casual look:

Knee-high boots:

In the cooler months, I truly love the look of over the knee boots and knee-high boots paired with skirts.

Whether it be a mini skirt that shows off the full over the knee boot, or paired with a maxi skirt with a slit, this combo is so cute and when paired with the right tops, this is a goo-to casual look that I will reach for all Fall/Winter long.

These knee-high boots would be perfect styled with casual skirt outfits:

knee high boot

Knee High Boot

Sandals

A pair of sandals is the most common casual shoe to wear, and is perfectly paired with skirts especially during the Spring and Summer months.

Whether it be flat sandals, strappy sandals or wedge sandals, they lend a truly effortless vibe that I just love! When it comes to pairing with a mini or midi skirt, flat sandals work great!

For a maxi skirt, I would opt for wedges or strappy sandals with a slight heel to offset the length of the skirt.

How to Create Casual Outfits with Skirts

When it comes to creating a casual outfit with a skirt, my general outfit formula is Color + Texture + Accessorize = Casual Skirt Outfit.

casual tennis skirt outfit idea

I like to keep these 3 things in mind as it tends to help to create cohesive looks while offering the laid back style I am going for.

First up, choosing the skirt. Whether it is a casual skirt or a dressier skirt, it can be styled casually. Just take note of the length, fabric (is it faux leather, or a sheer pleated skirt?).

Once that is determined, I move to texture. I want the top I pair with my skirt to be a contrast, especially if my skirt is a dressier fabric.

A faux leather skirt paired with a cotton graphic tee or knit oversized sweater offers a great balance. Finally, accessorize!

Complete your look with an appropriate shoe that is cohesive in colors and isn’t too fancy. Once you’ve locked down these 3 steps, you’ve created the perfect casual outfit with a skirt!

This casual mini skirt outfit is one that I would love to recreate!

The mini skirt is flirty and feminine with the pink floral print and flowy fit. Contrast the luxe fabric of the mini skirt with the casual knit in the oversized sweater and classic denim jacket, this is the perfect combination.

Add the final touch with a fun pair of casual sneakers and you’re ready for a lunch date.

I absolutely love this casual midi skirt outfit! This knit midi skirt can be easily dressed up with a bodysuit and heels, but when paired with a great pair of neutral sneakers and a cute graphic tee, it is instantly effortlessly chic and can take you from running errands to carpool.

Top with a faux leather jacket or cardigan for the cooler months.

Do you have a pleated maxi skirt in your closet? Don’t be afraid to style it casually!

You can pair it with a denim button down shirt – either tucked in or knotted at the waist, and a great pair of suede knee-high cowboy boots.

The casual elements in the top and shoes help to create this otherwise “dressier” skirt into the perfect causal look.

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