8 of the best transitional skirts to wear this fall - and how to style them

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BERLIN, GERMANY - JUNE 16: Actress and TV host Katrin Wrobel wearing a yellow midi skirt by Madeleine, black boots by Shoemates, a camouflage military jacket by Fucking Karma, a white t-shirt by Ohnegleichen and sunglasses by Flair during a street style shooting on June 16, 2020 in Berlin, Germany. (Photo by Streetstyleshooters/Getty Images)
Actress and TV host Katrin Wrobel wearing a yellow midi skirt by Madeleine, black boots by Shoemates, a camouflage military jacket by Fucking Karma, a white t-shirt by Ohnegleichen and sunglasses. (Photo by Streetstyleshooters/Getty Images)

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If you’re anything like me, end of summer blues always have you down — especially when it’s time to pack up my summer wardrobe and brace for the cold. Rather than packing things up until next year, I’ve decided to experiment with some of my favourite summer staples and wear them with my fall fashion looks.

One of the items that I’m not ready to put away just yet are skirts, especially because I’m always looking for new, easy outfits to wear on a day-to-day basis. There are plenty of fall looks you can create with different skirts, whether it’s long, short, midi, or mini, and you can definitely still rock them well into fall.

Below, shop a selection of the best transitional skirts and ways you can style each of them this season.

Shiny Satin Midi Skirt

Twik shiny satin midi skirt. Image via simons.ca.
Twik shiny satin midi skirt. Image via simons.ca.

A soft satin midi skirt that’s long enough to keep you warm, and simple enough to be styled in many different ways. The great thing about the satin midi is that it can be paired with any top, and looks great with either a pair of sneakers or heels.

For a casual look: Try it with a crewneck sweater or a tee if it’s warmer.

For a formal look: Pair your satin midi with any crisp white blouse.

SHOP IT: Simons, $39

Corduroy Pencil Skirt

Icone corduroy pencil skirt. Image via simons.ca.
Icone corduroy pencil skirt. Image via simons.ca.

Corduroy is a cold weather staple that’s bound to keep you warm. With a simple silhouette and versatile neutral black shade, you can’t go wrong with this corduroy option.

For a casual look: A long corduroy skirt paired with combat or leather ankle boots, and a plain white top is both super trendy and chic for the fall.

For a formal look: Switch the boots for heels, and since it’s a pencil skirt, adding the heels will instantly give it a more polished feel.

SHOP IT: Simons, $49

Faux-leather Midi Skirt

Contemporaine faux-leather midi skirt. Image via simons.ca.
Contemporaine faux-leather midi skirt. Image via simons.ca.

Fall is the perfect time to rock leather - including a leather (or faux leather) skirt. A long, leather skirt can be paired with high heel boots and a turtleneck sweater for a timeless and put-together outfit.

For a casual look: Pair this midi with a printed accessory like a purse or headband to add an element of fun to a neutral outfit.

For a formal look: Keep things monochromatic with a matching pair of tall leather boots.

SHOP IT: Simons, $79

ASOS DESIGN fluffy midi skirt in camel

ASOS DESIGN fluffy midi skirt in camel. Image via asos.com
ASOS DESIGN fluffy midi skirt in camel. Image via asos.com

A fluffy, knit midi skirt with a stretchy waist? Talk about cozy! I love that this look can be worn as a two-piece with the matching knit sweater or worn with any neutral top that’s already in your wardrobe.

For a casual look: Throw on sneakers, or printed shoes if you want to try something fun.

For a formal look: Pair this knit skirt with a blouse and checked blazer for a look that’s equally comfy and professional.

SHOP IT: ASOS, $54

Wash Lab Long Denim Skirt

WASH LAB long denim skirt. Image via nordstrom.com.
WASH LAB long denim skirt. Image via nordstrom.com.

A long denim skirt is a fall fashion item you definitely want to have in your wardrobe. This edgy, grey-wash denim skirt with a frayed hem can be worn with a tee, long sleeve, or turtleneck depending on the weather.

For a casual look: Keep it simple with basic tops, like your favourite graphic tee and leather booties.

For a formal look: Try out one of this season’s more eye-catching designs, like a blouse with an asymmetric neckline.

SHOP IT: Nordstrom, $128

Vero Moda Fidela Plaid Skirt

VERO MODA fidela plaid skirt. Image via nordstrom.com.
VERO MODA fidela plaid skirt. Image via nordstrom.com.

Personally, I love patterns for fall; they don’t look over the top and suit the fall aura. Here’s a plaid miniskirt that embraces the season and adds a nostalgic, schoolgirl feel.

For a casual look: Opt for a pair of sheer leggings and leather combat boots.

For a formal look: Embrace your inner Cher Horowitz and style it with knee high socks and patent heels.

SHOP IT: Nordstrom, $45

Loveappella Roll Top Maxi Skirt

Loveappella roll top maxi skirt. Image via nordstrom.com.
Loveappella roll top maxi skirt. Image via nordstrom.com.

If you want to make a statement this season, go for something in animal print. Since this Loveappella maxi skirt is printed, try keeping the rest of your outfit simple, with a plain top and booties.

For a casual look: Layer on an oversized denim or leather jacket to tie the outfit together nicely.

For a formal look: Dress things up with a sheer blouse for added sex appeal.

SHOP IT: Nordstrom, $49

Endless Rose Polka Dot Pleated Skirt

Endless Rose polka dot pleated skirt. Image via nordstrom.com.
Endless Rose polka dot pleated skirt. Image via nordstrom.com.

I’d say pleated skirts are an item you can sport year-round. This Endless Rose skirt is a funky look to try this season, perfect for a date or party, with a muted green tone that’s great for fall.

For a casual look: Tone down this full skirt’s dressy feel by pairing it with a chunky knit sweater or cardigan.

For a formal look: Go for a full-on party-ready look with a sweet ruffled blouse.

SHOP IT: Nordstrom, $80

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