Gray skirts are a wardrobe staple for women of all ages and professions. This classic piece is perfect for anything from business meetings to weddings and everything in between. 

A gray skirt is a timeless canvas waiting to be transformed into a chic outfit. Today, we’re diving into the endless possibilities of styling a gray skirt. 

We have 40 gray skirt outfit ideas for you to draw inspiration from.

So, grab your favorite gray skirt and take notes! Here’s the ultimate guide for what to wear with a gray skirt.


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Off-the-Shoulder Top & Sandals

gray skirt outfit blouse sandals

An off-the-shoulder top and sandals are the perfect way to dress up a gray skirt for summer. 

Wear a body-hugging black top and matching sandals or a flowy floral blouse for a more beachy look. 

Explore our selection of affordable vegan sandals

A Pink Sweater & Gold Belt

gray skirt outfit pink sweater belt

You can dress up a gray skirt with a pink sweater and gold belt for the office or a more formal occasion.

Gray, pink, and gold look great together. This outfit is timeless, elegant, and effortlessly chic. 

Check out our selection of sustainable sweaters made in the USA

A Black Blazer & Sneakers

gray skirt outfit blazer sneakers

A black blazer is a must-have for any professional wardrobe. Why not pair it with a gray pencil skirt?

Pair your look with brand-new white sneakers or casual slip-ons for a fun, unexpected twist. 

Shop our favorite elegant blazers for the perfect, polished outfit. 

A Classic White Button-Up

gray skirt outfit white button-up

A classic white button-up shirt tucked into a gray pencil skirt is a classic, timeless office outfit. 

The great thing about this outfit is how professional it looks. When in doubt, wear a well-tailored white shirt, light gray skirt, and low kitten heels. You’re sure to make a good impression no matter the occasion. 

Find your next perfect white button-up with these sustainable shirt brands


Other Neutrals

gray skirt outfit neutrals

Gray is a versatile, easy-to-wear color that anyone can pull off. When building an outfit around a gray skirt, choose other neutral colors. 

Neutrals like black, beige, camel, and white perfectly complement a gray skirt. Wearing other neutrals creates an air of class and elegance. 

You can use this method regardless of the season. Go with dark neutrals like navy blue or black during colder months and lighter colors like cream and taupe during summer and spring. 


Black Knee-High Boots & A Matching Shirt

gray skirt outfit knee-high boots

You can’t go wrong with black knee-high boots, a gray skirt, and a black shirt if you want something modern, edgy, and easy. 

This outfit looks fantastic on all body types. Wear a plaid gray mini skirt with sheer black tights to create the best version of this look. 

Don’t miss our selection of the best knee-high boots that are sustainable and vegan. 

Classic Tank Tops

gray skirt outfit tank tops

gray midi skirt black tank top

A classic tank top creates a laid-back and sexy look with any gray skirt. 

Wear a white ribbed tank tucked into a relaxed gray tennis skirt, or dress up a patterned midi skirt with a sleek black spaghetti strap top. Don’t shy away from creative color options like neon or pastel tank tops. 

Organic cotton tank tops are breathable and sustainable options to wear with a gray skirt. 

A Bright Embellished Sweater

gray skirt cute sweater

Embellished sweaters with gray skirts are an easy go-to for officewear. This outfit looks professional while still expressing your personal style. 

Wear a fun jewel-tone sweater with glittery beading or unique embroidery to liven up your favorite gray skirt. Pair your look with sheer tights, or simply wear some comfy flats. 

Check out these ethical and affordable brands if you’re looking for a new cute sweater. 

Tights & Ankle Boots

gray skirt ankle boots tights

Gray skirts come in all shapes and sizes. From tight minis to flowing maxis, every gray skirt looks fantastic with tights and ankle boots. 

Pair a tight gray skirt with black tights and heeled ankle boots, or wear a knee-length pencil skirt with matching boots and a camel coat for the ultimate chic look. 

Check out these eco-friendly tights and sustainable boot brands

Faux Leather Jackets and Lace-Up Boots

gray skirt outfit vegan leather jacket

Add a vegan leather jacket and lace-up combat boots to your gray skirt outfit if you want some extra edge. 

Black is always an excellent choice when it comes to jackets and boots, but don’t shy away from bolder colors like white, tan, and blue. If it matches your gray skirt, it’s a hit. 

Explore our selection of high-quality vegan leather jackets

A 90s-Chic Sweater Vest

gray skirt 90s sweater

Pair your loose gray skirt with an oversized sweater vest for a vintage 90s feel. 

This look is all about proportions, so focus on looser silhouettes with surprising cut-outs, like thigh-high leg slits or a deep v-neck. 

Layer your outfit with knee-high vegan leather boots and a white men’s button-up for an effortless vintage edge. 

Recreate this chic look with our selection of affordable sweater vests

An Argyle Sweater

gray skirt outfit argyle sweater

Argyle sweaters and gray skirts are perfect for a preppy outfit with vintage Clueless vibes. 

Wear a cute argyle sweater vest with a white t-shirt underneath, or rock a long-sleeve knit argyle with a high-waisted gray miniskirt. 

Finish off your outfit with ankle boots, a baguette handbag, and understated jewelry. 

Want more outfit inspiration? Check out these dark academia outfit ideas that look amazing with gray skirts and argyle sweaters. 

Halter Tops & Heels

gray skirt halter top

Create a dressy night out look with a halter top, strappy heels, and your favorite gray skirt. 

This outfit works best with a flowy, boho-inspired midi or maxi skirt. A halter top and heels capture a laid-back, beachy feel but with a touch of dressed-up elegance. 

Wear a gray skirt with a fun paisley or polka-dot print for extra boho vibes. 


A Classic Denim Jacket

denim jacket gray skirt

A gray skirt is timeless, so why not pair it with something just as classic? A denim jacket is the perfect piece of outerwear to complete any gray skirt outfit. 

This outfit looks great with any type of top, from a tucked-in t-shirt to a fun sequin tank top. Dress it up or down, depending on your mood. 

Shop our selection of sustainable denim jackets


A Collared Shirt Under a Sweater

gray skirt collard shirt

A collared shirt under a sweater makes a great preppy gray skirt outfit. 

Wear a white button-up shirt under a chunky knit sweater for a cozy fall vibe. If streamlined is more your style, wear a fitted sweater with a classic collared shirt in a neutral color. 

Gray pleated skirts or pencil skirts look best with this look. 


A Bandeau Top & Gray Midi Skirt

gray skirt bandeau top outfit

Try a bandeau top with a gray midi skirt for an elegant yet edgy evening look. 

The volume of the gray midi skirt balances nicely with the midriff-baring bandeau top, creating a look that is chic yet sexy. This look is perfect for a night out with the girls or a fun date night.

Don’t miss our selection of sustainable midi skirts

A Plaid Coat, Turtleneck & Fanny Pack Bag

gray skirt turtleneck coat

Gray skirts work for colder weather, too. Layer your favorite skirt with a plaid coat, neutral turtleneck, and trendy fanny pack bag. 

This outfit is all about playing with volume, so don’t shy away from looser fits and longer hemlines. Wear platform boots or vintage tennis shoes to complete your outfit. 

Explore the best organic cotton turtlenecks and sustainable winter coats


Create a Matching Set

gray skirt matching set outfit

Create a unique matching set by wearing a gray blouse with a cute gray skirt. 

You can wear a gray linen crop top with a matching button-up midi skirt. Pair a sheer gray blouse with a high-waisted mini skirt as another option. 

You can match your shades of gray perfectly or mix light and dark hues for an eclectic look. 


A Tank Top & Blazer

gray skirt blazer outfit

A tank top and blazer is an easy way to dress up a gray skirt. 

A tucked-in tank top is casual enough for a lunch date, and the blazer adds a touch of professionalism. So, you can easily transition this outfit from day to night. 

Check out these hemp blazers for the ultimate sustainable twist to your gray skirt look. 


A Classy Velvet Blouse

velvet gray skirt outfit

A classy velvet blouse with a gray skirt is a unique outfit idea for winter and fall. 

For extra oomph, create this look with a skirt made of velvet that shimmers in the light, adding extra movement and texture. 


A T-Shirt with Rolled-Up Sleeves

t-shirt with gray skirt

Wear an oversized tee with rolled-up sleeves for a casual, everyday look. 

Pair this top with your favorite gray skirt to add some elegance to this laid-back outfit. It’s comfortable, chic, and effortlessly cool. 

Find the perfect fit with these Canadian-made t-shirts


Bright Pink 

grey skirt with bright pink

Embrace your inner Barbie and wear bright pink with your gray skirt. 

You can wear anything from a bright pink blouse to a neon blazer. Pink is great with gray because these two colors balance each other out and create a bold yet refined look. 

If you can’t get enough of the pink trend, check out our tips on how to style a pink skirt

A Bodysuit

gray skirt bodysuit outfit

A bodysuit is an excellent idea if you want a curve-hugging, sleek look with your gray skirt.

Bodysuits range from simple t-shirt cuts to sexy off-the-shoulder looks. Choose a sustainable bodysuit that makes you feel beautiful, secure, and comfortable. 

Explore our selection of sustainable bodysuits

A Lace-Up Boho Blouse

gray skirt boho blouse

So, floral skirts aren’t your thing, but you still want those boho vibes? Try a flowy gray skirt and lace-up blouse. 

This feminine and relaxed outfit is perfect for any boho wardrobe. 

Check out the best affordable boho brands that we love. 

A Breezy Blouse and Sunhat

gray skirt sunhat outfit

A gray skirt is perfect for hot, sunny days because it’s breathable, stylish, and comfortable. 

Finish off this perfect summer look with a breezy blouse and cute sunhat. 

Check out our selection of sustainable blouses that match perfectly with gray skirts. 

An Oversized Sweater & Scarf

sweater gray skirt cozy outfit

Bundle up with a chunky knit sweater, scarf, and comfy gray skirt. 

This look is warm and cozy while remaining feminine and chic. Wear knee-high or ankle boots with a chunky heel for the ultimate fall aesthetic. 

Check out our guide on how to wear oversized clothes for tips and tricks to pull off this look. 


A Bright Yellow Top

bright yellow gray skirt outfit

The best thing about gray skirts is how easy they are to pair with any color. Bright yellow looks amazing with a gray skirt of any shade. 

Wear a bright yellow blouse tucked into a belted skirt, or tie up a sunshine yellow button-up and pop the collar for a preppy vibe. 

A Graphic Tee & Vintage Jacket

gray skirt vintage shirt jacket

A graphic tee and a vintage jacket look amazing with a gray skirt. 

Tuck in an oversized graphic tee to your favorite gray athleisure skirt for the ultimate it-girl outfit. For a skater vibe, wear a gray denim skirt, a distressed vintage tee, and a thrifted bomber jacket. 

You can shop for rare vintage finds on various online thrift store platforms

A Chanel-Inspired Cardigan

Chanel cardigan gray skirt

A gray skirt is a classic choice for a Chanel-inspired outfit. Wear a tweed cardigan with a high-waisted mini skirt for a fun, flirty, and chic look. 

You can upcycle a vintage designer piece or invest in a sustainably made cardigan. 

A Tropical Button-Up

tropical shirt gray skirt

Gray skirts aren’t always for formal occasions or the office. Wear a colorful tropical button-up with a midi A-line skirt for a fun, retro-inspired outfit. 

Tie up the front of your tropical shirt for some retro pin-up glam with a tiki twist. 

Fishnet Stockings and a Black Shirt

gray skirt fishnets black shirt

Pair your gray skirt with black fishnet tights and a black shirt for a simple, everyday look with some edge. 

Wear heels or sneakers, depending on the type of vibe you’re feeling. 

Shop for your next black t-shirt with our ethical, American-made shirt selection. 


A Crop Top

gray skirt crop tops

A gray skirt looks incredible with a fun and sleek crop top. 

This look is modern, sultry, and feminine. Show a little skin with a body-hugging cropped halter and low-waisted gray bodycon skirt. 

Wear a flowy, loose-cropped blouse with a high-waisted gray skirt to achieve this look without showing too much midriff. 

Don’t miss our selection of the best sustainable crop tops


A Girly Floral Blouse

gray skirt floral blouses

A floral blouse is always a good idea. Wear a gray denim skirt with a white floral blouse for a cute summer look.

You can also wear a strapless floral bandeau top with a loose gray midi or maxi skirt for a boho-inspired feel. 

A Sheer Blouse

sheer blouse gray skirt

A sheer blouse creates a sexy, fun outfit when paired with a gray skirt. 

Wear a sheer babydoll blouse with a bandeau or tank top underneath for a playful evening look. 

If you’re looking for tips to pull off this look, try our guide on what to wear under a sheer shirt


Bright, Bold Colors

gray skirts bright colors

A gray skirt is a blank canvas with incredible outfit opportunities. Why not wear bright, bold colors? 

Make a statement with bright neons, rich jewel-tones, or sweet pastels. Wear a flowy pastel pink top, neon striped t-shirt, or jewel-tone sweater with your favorite gray skirt. 

If a vibrant fashion style is for you, wear bright, bold colors with your gray skirt. 


A Faux Shearling Coat & Black Tank Top

gray skirt faux shearling coat

Be bold in a faux shearling coat with a simple black tank top underneath. 

The boldness of the faux fur nicely compliments the understated elegance of a gray mini or bodycon skirt. 

Pair your look with stiletto heels and a black crop top for the perfect girl’s night out look. 

A Front-Tie Blouse and Platform Shoes

front tie blouse gray a-line

A cropped front-tie blouse with a full A-line gray skirt creates a sexy, retro-inspired look that looks great across seasons. 

Add an extra layer of edginess with chunky, black platform shoes. Add a headband and vintage handbag, and you’ll be rocking this 90s grunge-inspired look in no time. 

Crochet Tops

crochet tops gray skirts

Create a cute and trendy look with a crochet top. From tank tops to cardigans, anything crocheted is bound to look good with a gray skirt. 

Go for crochet tops with colorful yarn, unique granny square patterns, and a comfortable fit. 

Learn more about how to style crochet clothing

A Striped T-shirt

striped shirts gray skirt outfit

You can’t go wrong with a gray skirt and striped t-shirt. 

Tuck a black-and-white striped boatneck into a high-waisted gray midi skirt for a fun Parisian flair, or wear a striped baseball tee for a casual, laid-back look. 

Top off your look with your favorite pair of sneakers, and you’re ready for whatever the day may throw your way. 


A Trench Coat and Tights

gray skirt trench coat

Create a chic winter look with an elegant trench coat over your favorite gray skirt. 

Wearing tights underneath gives this look an extra layer of warmth.   

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About the Author: Liz Flynn

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