Long skirts are having a major moment right now in fashion.
Plus, long skirts are comfortable, move with you and make getting dressed a breeze.
As a stylist, I love helping my clients discover new ways to wear long skirts to suit their personal style.
For each skirt style, I’ll recommend specific tops, jackets, shoes and accessories to create a polished, pulled-together look.
I’ll also share my professional styling advice for choosing the most flattering skirt lengths, fabrics, silhouettes and colors based on your body type and style goals.
Boho Maxi Skirt Outfit
Channel your inner boho goddess with a breezy maxi skirt in a floral or paisley print.
These free-flowing, ankle-length skirts have an effortlessly chic vibe perfect for warmer weather.
Look for a maxi made of lightweight, natural fabrics like cotton, silk or rayon that sways with every step.
A high waist or empire silhouette will cinch your waist and prevent the skirt from feeling too overwhelming on a petite frame.
Taller women can opt for a maxi with side slits for greater ease of movement.
On top, pair your maxi with an off-the-shoulder peasant blouse or wrap top to enhance the relaxed bohemian aesthetic.
Adding a jean or leather jacket makes this outfit suitable for running errands while staying true to your style. Slide into flat sandals or espadrilles to complete this unfussy, boho chic look.
To accessorize, stack up some beaded bracelets, pile on long necklaces with pendants and don a wide-brim hat or printed headscarf.
Oversized sunglasses and a woven shoulder bag also accent this look nicely. Feel free to get creative and express your free-spirited personality!
Midi Skirt with T-Shirt and Sneakers
My next favorite way to wear a long skirt is with a simple tee, sneakers and a midi skirt for a casual street style vibe.
Midi skirts hit below the knee, making them office-friendly while still showing some leg.
A-line and wrap silhouettes work well here for a universally flattering shape. Look for one with a comfortable elastic waistband that you can pair just as easily with heels as with sneakers.
On top, an oversized graphic tee adds a sporty, laidback edge.
Tuck just the front into your skirt and let the back hang loose. Ground the outfit in minimal white sneakers—wrap a colorful scarf around the back of your neck if you need more warmth.
Accessorize with stacked bracelets, simple stud earrings and a crossbody bag.
Throwing on some retro cat-eye sunglasses completes this effortlessly cool weekend look.
Denim Midi Skirt and Cropped Jacket
One of my favorite styling tricks is pairing a denim midi skirt with a cropped jacket.
This outfit flatters all body types and really elongates your silhouette.
Go for a classic A-line denim skirt in a medium or dark wash — the buttons down the front add a retro touch.
Pair it with a collared crop jacket; you can try a denim, corduroy or light wool fabric.
For petite women, choose a midi skirt that hits above the ankles to avoid shortening your legs.
Tall ladies should opt for a maxi length instead.
Finish the outfit with a graphic tee or tank tucked in, low top sneakers and small hoops or studs.
Add a thin belt at the waist if desired, or cinch with a modern fanny pack.
Stuff your essentials in a small crossbody bag. You’ll look casually polished andPullon with this timeless combo.
Slip Skirt 
Long skirts aren’t just for weekends — they make incredibly chic workwear too.
Take this outfit formula: a flowy slip skirt paired with a crisp sweater or blouse.
Look for a midi skirt with an A-line or pencil shape made of silky material like satin or crepe. A high waist elongates while a knee-length hem keeps it office-appropriate.
Neutral hues like black, navy or tan are versatile colors.
Tuck in a collared sleeveless sweater or long-sleeve blouse; jewel-toned colors complement neutrals nicely. Finish with pointed toe flats and simple stud earrings.
For cooler weather, add tights and ankle booties. You can even layer a blazer or trench coat on top.
This elegant outfit flatters all figures.
The slip skirt slims your silhouette while the tucked-in sweater defines your waist. Turn heads at the office with this sophisticated long skirt outfit!
Faux Leather Midi With Edgy Top
If your style skews more rock n’ roll, try a fitted faux leather midi skirt with an edgy graphic tee and moto jacket.
A vegan leather midi skirt in black or bold red makes a sleek style statement.
Look for one with a touch of stretch so you can walk and sit comfortably. Pair it with a drapey tee featuring punk graphics or band logos.
Add a cropped moto jacket in a coordinating color.
Chunky ankle boots with a low block heel complete this downtown cool look. Studded crossbody bags, choker necklaces and stackable bracelets make edgy accessories.
This outfit highlights your assets while keeping true to an edgy aesthetic.
The fitted midi skirt flatters your curves, while the graphic tee and moto jacket convey attitude. Style your long skirt with a little rebellious flair!
Romantic Midi With Ruffles
Do you fancy yourself a modern-day heroine from a Jane Austen novel?
This romantic midi outfit has you covered.
Seek out a midi skirt with feminine ruffles, florals or lace trim.
Pair it with a ruffly Victorian blouse or an off-shoulder top with billowy sleeves.
Soft pastels like mauve, sky blue and peach make sweet color combos.
Slide your feet into Mary Jane heels or ballet flats. Carry a small structured handbag like a heart-shaped box clutch. Don’t forget dainty jewelry like pearl studs or a cameo necklace.
The ruffles, pastels and delicate details give this outfit a dreamy, romantic vibe. The midi skirt shape remains modern. Add a cardigan or peacoat for seasonal versatility.
You’ll feel like the leading lady wherever you go in this youthful, feminine look!
Textured Midi With Turtleneck
Do you adore autumnal style? This cozy ensemble mixing textures is sure to inspire you.
Start with a midi skirt in a rich fall hue like hunter green, burgundy or mustard. Choose one with tactile fabric like tweed, corduroy or faux suede.
These materials add visual interest while keeping you warm.
On top, layer a fitted turtleneck underneath a chunky cardigan or oversized sweater. Finish the outfit with suede ankle booties with block heels for all-day comfort.
Carry a large shopper tote to hold your essentials.
You can even belt the sweater for more definition if desired. Bold hoop earrings, a wide headband and an oversized watch make stylish accents.
Shirtdress with Knee-High Boots
For an effortlessly stylish fall outfit, you can’t go wrong with a long shirtdress and boots.
This combo exudes polish.
Look for a collarless shirtdress made of lightweight material like rayon or polyester; midi and knee-length styles work well.
Neutrals like black, olive and gray make this dress more versatile.
Layer it over a turtleneck or collared shirt for extra coverage. Pull on a pair of sleek over-the-knee boots in leather or suede.
Carry a structured top-handle satchel bag for daytime chic.
The shirtdress skims over your figure, while the contrasting boots elongate your legs for a slimming effect. Dress it up with a fedora,statement sunglasses and bold cuff bracelets.
With tights underneath, this stylish outfit will take you through fall in elegance.
Slip Skirt and Moto Jacket
For nights out, transform your slip dress into a long skirt outfit by pairing it with a moto jacket and tall boots.
A silky spaghetti-strap slip dress makes a sensual midi length skirt when worn with a jacket on top.
Look for one with subtle lace trim or mesh accents to elevate the lingerie vibe.
Layer on a black or blush pink moto jacket, leaving it open to reveal the dress. Then pull on over-the-knee boots in leather or suede to complete the outfit.
Grab a small leather shoulder bag and add delicate body jewelry, like a thin choker necklace or lariat with a pendant.
Apply a bold red lip and style your hair down to accentuate the feminine, flirty energy.
The slip dress hugs your curves, while the moto jacket adds attitude. Paired with sultry over-the-knee boots, this good girl gone bad look inspires confidence for a night out dancing.
Button-Front Midi and Cropped Sweater
Here’s another office-ready ensemble: try pairing a button-front midi skirt with a cropped sweater.
Look for a midi skirt with functional buttons down the front and side pockets for a timeless silhouette.
Solid colors like navy, black and camel work well for the office.
Tuck in a cropped crewneck or mock neck sweater. Long sleeves balance the shorter hem. Complete the outfit with loafers or block-heel booties.
Stow small essentials like your phone, cards and lipstick in the skirt pockets. This streamlined outfit exudes professional polish.
For cooler weather, finish with tights layered under the skirt.
The button-front midi flatters your shape while remaining appropriate for work. Cropped knits show just a sliver of skin, keeping the vibe modern but still sophisticated. This pair means business!
’60s-Inspired Mod Outfit
Get playful with this ‘60s-inspired mod mini outfit in bold retro prints.
A knee-length A-line skirt with a high waist looks straight out of the ‘60s.
Try an eye-catching print like polka dots, chevron stripes or fun florals to liven things up. Pair it with a collared blouse or lightweight turtleneck.
Finish with patent leather flats or Mary Janes. White go-go boots also channel the era perfectly.
Top with a beret or pillbox hat for extra retro vibes. Carry a colorful structured handbag or novelty clutch.
The short hemline, graphic patterns and mod accessories give this otherwise classic outfit a youthful twist. It’s eye-catching yet tasteful—perfect for standing out with ‘60s flair!
Tweed Pencil Skirt and Button-Up
For the office, nothing looks sharper than a tweed pencil skirt with a button-up blouse. This pairing oozes retro elegance.
A high-waisted knee-length pencil skirt nips in your waist.
Look for one woven from textured tweed or bouclé fabric for dimension.
Neutrals and pastels suit both winter and spring palettes.
Tuck in a collared button-up blouse, either long-sleeve or sleeveless.
Tailoring flatters while the pencil skirt streamlines your shape. Pointed toe pumps dress up the look.
Carry a structured top-handle bag or hard case clutch. If needed for warmth, finish with a peacoat or wrap coat over top. Elegant pearls make a timeless accessory choice.
This outfit has a classic retro secretary vibe. The tailored tweed pencil skirt slims while the button-up blouse keeps things proper and polished. It’s bombshell chic!
Long Slip Skirt and Button-Down Shirt
If you prefer minimalist style, this effortless long slip skirt and button-down shirt outfit is for you.
A straight slip midi skirt acts as a blank canvas. Solid black, white and beige are perfect versatile neutrals. Cotton, silk and satin versions work well.
On top, layer a menswear-inspired oversized button-down shirt, leaving it untucked. Roll up the sleeves for a relaxed vibe. Finish with box-fresh white sneakers, a sleek watch and small hoops.
This pared-back combo works everywhere from brunch to the office. Dress it up with heeled booties and a clutch or keep it low-key with strappy sandals.
The simplicity lets your personal style shine through.
The slip skirt flatters without clinging.
An oversized button-down adds laidback polish. This easy outfit proves getting dressed can still be unfussy and chic!
Wrap Maxi Skirt and Cropped Cami
My final long skirt outfit idea combines a flowing wrap maxi with a cropped camisole top.
A jersey or satin wrap maxi skirt with a thigh-high side slit exudes effortless glamour. The wrap silhouette flatters every figure by cinching your waist.
Neutral metallics like pewter, silver and champagne make it easy to dress up.
Pair it with a sleek cropped camisole and strappy heeled sandals for a sultry evening look. Or try it with a fitted cropped tee, jean jacket and sneakers for daytime wear.
Stacking skinny bangles and hoops keep it sexy yet casual.
The fluid maxi skirt moves beautifully while showing some leg.
Cropping your top keeps things youthful. Take this outfit from farmers’ market to date night by swapping out a few accessories.
The wrap silhouette fits snugly around your waist then flows out freely. Paired with a cropped top, this outfit celebrates the long skirt look from all angles.
Which was your favorite long skirt outfit? Let me know in the comments below!
There’s a perfect long skirt look out there for everyone.
With the right silhouette, length, color and styling, you can highlight your best assets in a skirt that makes you feel amazing.
The most important tip I can give is to have fun playing with different pieces already in your closet.
Tuck in a tee, throw on a jacket or choose an unexpected shoe. Don’t be afraid to get creative and express yourself through how you style your long skirt.
Figure out if you prefer to wear yours dressed up or down.
See what types of shoes and tops you feel most confident in. The right outfit can make any ordinary day feel special.
Long skirts are truly timeless, so I know you’ll get great cost-per-wear from these versatile pieces.
Hopefully you’re feeling inspired now to experiment with fresh new ways to rock them!
Up next, I may just have to cover chic outfit ideas for the ultimate wide-leg pants trend.
Until next time, happy styling!
