How to Style a Maxi Skirt

Maxi skirts are a great style choice no matter what the season. In the winter, they can keep your legs a little bit warmer by covering up more skin, and in the summer, they can keep you cool by providing a bit more breathability than pants. They come in every color of the rainbow and are available in any style imaginable, from more form-fitting options to flowier, more bohemian looks.

If you’ve never worn a maxi skirt before, you may be at a little bit of a loss as to how to style one. You may wonder what type of shirt to wear with a maxi skirt or what shoes to wear or even what jewelry to accessorize with. There is no single correct way to wear a maxi skirt. Like any other piece of clothing, it’s yours to style however you want and to truly make your own.

Still, there are plenty of commonly accepted ideas out there about maxi skirts and popular ways to wear them. Today, we’re here to share some of our favorite maxi skirt styling tips. Browse this list and try these ideas for yourself. Feel free to mix and match a few of them together, or take inspiration from them and make your own ideas. As long as you’re having fun and feeling comfortable and confident, there are no wrong answers. Before we get into specific tips, let’s start with the basics.

What Is a Maxi Skirt?


The maxi skirt will be the centerpiece of any outfit it’s a part of. By their very nature, these skirts are eye-catching pieces that always make a statement. They’re made up of so much fabric that the eye is naturally drawn to them, even if they’re not a bold print or pattern. Traditionally, a maxi skirt is long enough to brush the ground or at least the tops of your shoes. The skirt is usually loose and billowy, with enough fabric to spare that it flows loosely around your legs as you walk.

Maxi skirts can be worn at almost any occasion, depending on how they’re styled. They can easily be dressed down and worn around the house, at a barbecue or even at the beach. They can also be dressed up and worn to work or a formal event.

Typically, the major advantages you’ll notice with a maxi skirt are:

  • Comfort: Maxi skirts are extremely comfortable. They offer complete breathability and freedom from any tightness or squeezing in the legs or hips that you might experience with pants or tighter skirts.
  • Freedom of Movement: Where tight pants or skirts tend to restrict your movement, whether that movement might be bending over, taking larger steps or just curling up comfortably in a chair, maxi skirts allow for complete freedom of movement.
  • Peace of Mind: We’ve all been in that position where we’re wearing a shorter skirt, and we find ourselves constantly worrying if it’s riding up and showing too much skin. From constantly tugging the skirt down over our thighs or worrying about bending over, these types of skirts can be stressful. With maxi skirts, you can have the confidence you need to never worry about these problems again.
  • Versatility: Maxi skirts are one of those great pieces to have in your wardrobe that offer almost chameleon-like powers of transformation. From daytime to nighttime and from the casual to the formal, the maxi skirt can be dressed up or down to suit virtually every occasion.

Styling Your Maxi Skirt: The Elements to Consider

When it comes to thinking about how to wear a maxi skirt, there are a few different elements you have to play with. By mixing and matching these various elements and swapping them out, you can achieve vastly different looks even if you wear the same skirt for every outfit. Let’s look at all the different pieces you have to work with and how they contribute to the final appearance of an outfit.

1. The Skirt

Of course, the skirt itself will be the focal point of any outfit. This should usually be the first piece you select, and once you’ve picked this out, you can build the entire outfit around it. Choose from fuller maxi skirts to slimmer ones, solid colors to wild prints, and ones that trail along the ground to ones that just come to the tops of your shoes.

2. The Top


Next to the skirt, this is the most important piece of your outfit. Based on the type of shirt you pick, you can go a long way toward making your maxi skirt look either super casual or very formal. This is something you’ll want to keep in mind when choosing a shirt.

While there are no hard and fast rules regarding what shirts to wear with a maxi skirt, there are a few definite trends that are widespread enough to take notice of. Here are a few things to think about when choosing tops to wear with a maxi skirt:

  • Avoid the Long and Loose: Your maxi skirt will already be long, loose and billowy. If your shirt offers this same type of vibe, the two clash with one another. To balance out the loose flowiness of your skirt, opt for a top that fits closer to your body.
  • Don’t Go Past the Waist: This isn’t one that you need to follow 100 percent of the time, but it is a common choice. Avoid shirts that hang past the waistline and drape over the top part of your skirt. This may be slightly more acceptable with a sweater or a dressier shirt, but a good rule of thumb to follow is that your top shouldn’t extend past the waistband of your skirt.
  • Tuck It In: This idea goes hand-in-hand with our last tip. If you want to pair a certain top with your maxi skirt, but you think it might be too long to go with the skirt, there’s an easy fix, and that’s to tuck it in.
  • Add a Belt: Not every outfit needs a belt, and you’ll want to exercise your judgment as to whether your outfit needs one or whether you’re comfortable adding one. But with many tops, belts do a great job of defining the waist, providing a much-needed break in the silhouette created by a maxi skirt.

3. The Jacket

Not every maxi skirt outfit needs a jacket. Particularly if it’s summer and you want to go casual, a jacket might be completely unnecessary. But if it’s chilly out or you want to make a maxi skirt look appropriate for the office, sometimes a jacket is in order.

The biggest thing to remember about pairing a jacket with a top and over a maxi skirt is that jackets are not subject to the same rule about not extending below the waistline. As a matter of fact, jackets are encouraged to go below the waistline.

Picture it like this:

  • A maxi skirt that’s belted around your natural waist.
  • A T-shirt that’s tucked into the waist of that skirt.
  • And a blazer or a bomber jacket that reaches down to about the level of your hips.

By having these different varying levels that all contrast with one another, it makes for a more visually appealing outfit with different textures and dynamics to keep things interesting. In most cases, the jacket should also be slightly looser, to contrast with the tighter shirt on underneath. Rarely would you button a blazer or zip up a jacket when you’re wearing a maxi skirt, and instead you would wear it hanging open.

4. The Shoes


Once you’ve got the bare bones of your outfit — the skirt, top and jacket, if there is one — it’s time to fill out the edges and dress it up with all the extras. In this case, this means the shoes.

The sky is really the limit when it comes to choosing the right shoes for a maxi dress, and we recommend taking your cue from the rest of the outfit as you select your shoes. For example, are you going for a casual beachy look for the summer? We recommend a pair of strappy flat sandals. Are you headed in for a day at the office? Classic pumps will get the job done. And for a Saturday morning brunch at a trendy restaurant? Ballet flats might be just the thing to finish your outfit off with style and elegance.

5. The Accessories


As a finishing touch, remember that no outfit is truly complete without a piece of two of carefully-selected jewelry. As with your shoes, look to the rest of your outfit for inspiration, choosing items that will connect with the rest of your outfit and truly set it off with style.

Some pieces to consider include:

  • Necklaces: A long, sweeping pendent necklace can harmonize beautifully with the long, sweeping lines of a maxi skirt.
  • Earrings: A large pair of statement earrings can be just the thing to make a maxi skirt look more professional, formal or casual, depending on the earrings.
  • Bracelets: While it depends on the individual piece itself, bracelets have a fantastic way of making any outfit appear a little more bohemian-chic. If you’re going for this casual and trendy look, a bracelet can be a quick way to achieve your goal.
  • Handbag: The most functional accessory of all, handbags range from the extremely formal clutch to the traditional purse and the casual messenger bag. Select the one that goes best with your outfit and make it the finishing touch.
  • Sunglasses: If you’re headed to the beach, an outdoor wedding or a stroll in the park, don’t forget a pair of fashionable shades that match the rest of your outfit.

What to Wear With a Maxi Skirt

We now know all the different pieces that warrant consideration as you style a maxi skirt. Now, it’s time to put those pieces together and consider a couple sample maxi skirt outfit ideas.

1. The High-Low Maxi Skirt

Let’s say you’re looking to style this beautiful chambray high-low maxi skirt. While the gorgeous pastel blue makes it a perfect fit for springtime or even summer, you could totally rock this during the winter as well. We recommend dressing something like this down to be a little more casual — think a trip to the mall or a lunch date with friends. Here’s one sample look to try with this skirt:

  • The Top: With the high-low design of this skirt, there’s a lot to catch the eye. Because of this, it’s a good idea to keep things simple on top. We think a white blouse would be a great way to go, tucked in loosely at the waist. Go for a short-sleeve or tank-top blouse for the summer, and hunt for something with longer sleeves to bring this piece into the winter.
  • The Jacket: If you wear this skirt in the springtime, it doesn't necessarily need a jacket. If you’re cold and looking to bundle up a bit, try going for a shirt with long sleeves or a coat you can take off once you get to your indoor destination.
  • The Shoes: Grab your favorite pair of heeled sandals or even flat sandals to really complement the loose, flowy lines of this skirt. High-heeled pumps are a possibility as well, but they may present a more formal appearance that doesn’t mesh as well with the casual feeling of this skirt.
  • The Accessories: Remember that the skirt is the star of this outfit. When it comes to jewelry, you’ll want to keep things pretty uncomplicated. A bracelet, watch or a pair of earrings might be just the thing to set this skirt off without overpowering it.

2. The Maxi Dress


Do you like the look and feel of a dress some days instead of a skirt? If you’re looking for a maxi dress to style, look no further than this Macie black floral maxi dress. With its three-quarter-length sleeves, darker color palette and floor-sweeping skirt, it’s a great look for a day out in the fall or winter. Here’s what to wear with it:

  • The Top: Because this one’s a dress, you don’t need to worry about a top. Something to note for future occasions, however, is that most maxi dresses can transform into maxi skirts by throwing a new blouse or sweater over the top, disguising the fact that it’s a dress. If you’re ever looking to take a look from day to night or disguise the fact that you’ve worn the same dress two days in a row, this is a great way to do it.
  • The Jacket: Feel free to add something like a denim jacket over this one if you want to make it a little more informal, or skip the jacket if you’re going for a dressier appearance. Even a denim button-up that’s left unbuttoned but tied in the front can be a great way to accessorize this dress.
  • The Shoes: Classic pumps will pair nicely with this dress and can elevate it to become a bit dressier if you’re heading into the office or an official event of some sort. If it’s chilly out and you’re looking to stay warm, a pair of ankle booties is also a great choice.
  • The Accessories: Because the entire dress is the same pattern, it might be nice to break up this pattern with a long tiered of pendant necklace. Some statement earrings are also a great way to finish off this dress.

3. The High-Low Wrap Dress


This dusty pink high-low dress is so gorgeous, you will want to wear it all the time. It’s a perfect example of a dress that looks casual by itself but can easily be dressed up for more formal occasions, using the principles of maxi dress styling. Here how to do it:

  • The Top: Again, there’s no need for a top here. Leave it as-is for a cool, breezy and summery look for all your get-togethers. If you are looking to throw a blouse over the top and transform this look, we’d recommend something white and delicate to complement the dusty pink and the soft lines of the skirt itself.
  • The Jacket: Throw a blazer over your shoulder and watch this dress transform from a light-hearted day dress into a business-chic outfit that’s totally office-appropriate.
  • The Shoes: Headed to hang out at your friend’s backyard party? Throw on a pair of strappy sandals. Headed to work? A pair of nude-colored pumps makes a great choice to accompany this muted pink shade.
  • The Jewelry: Opt for a long pendant necklace here to add decoration to the top of this dress. Because the sleeves are short and your arms will likely be bare, bracelets are on the table as well and can be a perfect way to dress things up a little. If you’re going with the blazer-and-office-fashion look, an elegant watch is always a winning choice.

4. The Casual and Carefree Look


We’ve spent a lot of time talking about looks that are great for the office, a date or a party of some kind. But what about the days where you’re looking for something extremely casual and comfortable that still makes you feel confident and love your look? We think a great way to achieve this style is to opt for a straight and solid-colored skirt. Pick your favorite color — gray, turquoise, red or any other color you like. From there, here’s how to style it:

  • The Top: If you’re looking for that casual "I-just-threw-this-together" look, you can’t go wrong with a simple graphic tee. The secret, of course, is to make sure that the colors in your T-shirt accentuate or nicely contrast the color of the skirt. Secondly, you’ll want to style the T-shirt. Tuck it in loosely or go for a stylish French tuck. Alternatively, if the shirt has enough extra fabric, gather the bottom together and tie it off to the side, tucking the knot under. All of these styles convey that effortless vibe that works so well in casual settings.
  • The Jacket: If it’s warm out, skip the jacket altogether. If you’re looking for another layer, go for a denim jacket or perhaps a stylish bomber jacket.
  • The Shoes: Take your cue from the season. If it’s summertime, flip-flops or your favorite pair of sandals are in order. If it’s a little chillier out, you can probably get away with your favorite pair of Converse or even ankle boots. 
  • The Accessories: If you choose to wear any jewelry with this outfit, keep it straightforward and don’t get too fancy or expensive. Choose something like a novelty fashion necklace or a charm bracelet, rather than diamond earrings. Don't forget to add your favorite pair of sunglasses if you're headed out, and you're good to go.

Shop Maxi Skirts and More at My Sister's Closet Boutique


Hunting for an outfit for your upcoming date or wedding? Wishing you had another outfit to wear to the office? Just looking for something you can endlessly re-style to suit the occasion? For all these times and more, a maxi skirt is the perfect solution.

Shop maxi dresses, skirts and so much more here at My Sister’s Closet Boutique, an online boutique where we specialize in comfortable and happy clothes that make you feel great and you’ll love wearing, all at prices you can afford. Browse our full catalog today and see what treasures you can add to your closet.