Perfect Pairings: 7 Ways To Wear Shirts With Skirts

Like salt and pepper or a gin and tonic, some things just aren't complete without their natural complement. Skirts and shirts definitely fall into this category. That said, they can be surprisingly tricky to match for two articles of clothing that are only one letter apart.

Choosing which shirt to wear with which skirt starts with easy considerations like color or matching details, but it quickly evolves into a proportions game. Here are our favorite options for which shirts to wear with skirts for dozens of unique outfits.

How To Choose Which Shirts To Wear With Skirts

Make the perfect match by selecting shirts that go with skirts with these guidelines.

Don't Waste Your Waist

The first place to start a skirt-shirt journey is with your natural waist. While defining a waist or creating an hourglass shape doesn't have to be the "goal" of every outfit, it's helpful to be aware of where your natural waist sits when combining separates.

To find your waist, bend over to the side with a bra on. The place where your abdomen creases along your oblique is your natural waist. This spot is different on each individual body, so it may be just above your belly button or significantly higher, approaching your rib cage.

If you struggle with how to wear shirts with skirts, it may be because you're placing your skirts too low. Try situating a skirt's waistband at your natural waist and tucking a fitted shirt into the waistband. If necessary, hide where the waistband and shirt meet with a thick belt. This quick cheat instantly gives classic proportions to your outfit.

Match the Skirt Aesthetically

A skirt and shirt should have some aesthetic quality in common when worn together. This can be  the same main color or accent color, or it can be the same texture, pairing a sheer skirt with a sheer top. Level up your pairing game by matching the accent on a skirt to the accents on a shirt — for example, pair studded denim with studded leather or a rhinestone skirt with jeweled shirt buttons.

Contrast the Skirt's Volume

Create a standout silhouette by choosing the opposite volume for your shirt that you chose for your skirt. For example, pair a wide and flowy skirt with a tight top or a hip-hugging pencil skirt with a voluminous top. This contrast, along with a defined waistline, is the key to how to wear a shirt with a skirt and nail the proportions.

7 Ways To Wear Shirts With Skirts

Now that you have the basics down, here are our favorite skirt and shirt-based outfits.

1. Tight Shirt, Belt, and Midi Skirt

This is an easy starting place for skirt and shirt outfits, but easy doesn't have to mean boring. Choose a bold printed midi skirt and an asymmetrical shirt to add interest, and don't forget the chunky statement belt. Adding a belt unites the two parts of the outfit and provides a template for other accessory decisions, such as your bag and jewelry.

Why a midi skirt? Since everything in this outfit stays close to the body, the extra length adds some visual heft to balance the look. Too many tiny pieces can make an outfit feel low-impact. If you want to wear a shorter skirt instead, try adding a longline coat overtop to achieve the same effect, like Kendall Jenner in her Matrix-esque long leather duster.

2. Long-Sleeve Shirt and Flowy Skirt

For fall and winter, try a tight long-sleeved shirt with a wide and flowy skirt. These skirts tend to look best when worn at the natural waist since all that skirt fabric tends to nip in the wearer's waistline. If you have a favorite pair of statement boots, go for a high-low flowy skirt to show them off.

3. Crop Top and Tulle Skirt

Now we're getting into advanced proportions territory. A fluffy tulle skirt is the ultimate in visual volume. Contrast it with a sleek or oversized crop top for a runway-ready silhouette.

4. Oversized Shirt and Pencil Skirt

A pencil skirt is the best piece to match with all of your blousey, puff-sleeve, or otherwise oversized shirts. To best contrast these elements, tuck the shirt in while leaving some fluffy volume on top. Then, match any details on the pencil skirt to your jewelry and accessories.

5. Matchy Skirt, Shirt, and Belt (Faux Dress)

With a little ingenuity, you can create a "dress" out of any matching shirt and skirt in your closet. Simply pull the skirt up to your natural waist and join the two pieces with a thick belt. Tank tops tend to work best, but you can use any shirt in the same color and texture as your favorite skirt.

6. High Glam Top and Maxi Skirt

Skirt and shirt outfits are great for everyday wear, but they also make a great alternative to a formal dress. Celebs love to wear a top with a maxi skirt on the red carpet. Sparkly, small tops with black skirts are always a safe bet, but you can also go menswear-inspired with a button-down shirt and maxi skirt.

7. Summer Tank and Circle Skirt

There's no substitute for the feeling of a flowy, airy circle skirt in summer. Instead of buying a thousand sundresses, give your wardrobe more versatility by opting for circle skirts, instead.

A long circle skirt (named for how the skirt is cut, a large circle with a donut-hole cutout in the middle) can easily transition from a summer wardrobe into fall and winter. A circle skirt with a tank top is a classic combination that's both comfy and stylish.

Shop the Latest Styles for Your New Favorite Shirts To Wear With Skirts

Learning different ways to marry shirts and skirts opens up new dimensions for your wardrobe and your personal style. Having trendy and interesting shirts to wear with skirts helps spark outfit inspiration. At Kate Hewko, we believe in stunning outfits for every body at every age. Browse our skirt picks for the latest styles.

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