Maxi dresses, as we all know, are not only one of the most comfortable, flattering, and forgiving items of clothing to wear, but they’re also surprisingly versatile too. They’re easy to add layers over as well as hide layers under, making them the perfect transitional piece for the coming fall months where some days are super chilly and others are still warmed by the summer sun. This alone makes maxi dresses and skirts my favorite pieces to wear for fall but they’re also a fantastic way to extend your summer wardrobe and get creative with pieces you already have in your closet as well as fun accessories.
From dressed up fancy to a little bit funky, work appropriate to playful weekend ensembles, here are 21 different ways I’ve transitioned my favorite maxi dresses and skirts for fall and worn them over and over again.
Add a Trench! 1 of 21
My favorite time of year to wear my classic shorty trench is fall and spring! And it's a perfect addition to solid color maxi dresses and fun prints like this one, adding a hint of classic chic!
Check out more photos & outfit details for this look here | Floral Maxi Dress with a Short Trench
Sweater & Boots 2 of 21
Denim Button Down 3 of 21
This vintage denim button down shirt worn over a jersey maxi is a bit more unique than a jacket or cardigan and still keeps me warm enough for a daytime fall excursion. Add a bold bag or clutch for a color and fun rhinestone statement necklace for sparkle!
Check out more photos & outfit details for this look here | Gray Jersey Maxi Dress with Denim Shirt
A Corduroy Blazer 4 of 21
Another look at my bright blue jersey maxi dress and here I paired it with a cozy vintage corduroy blazer and leather cognac belt and boots for a cozy chic fall look with a nod to the 70's.
Check out more photos & outfit details for this look here | Bright Blue Jersey Maxi with Cognac Blazer
80’s Meets 50’s for the Win 5 of 21
I love this fun 80's full-skirt maxi but to warm it up a bit I added a white button down and tied it at the waist, giving it a retro 50's look. The cognac accessories are the perfect color for fall.
Check out more photos & outfit details for this look here | Maxi with Tied UP Blouse
White After Labor Day 6 of 21
Fashion is for breaking the rules and wearing white after Labor Day is the number one breakable rule. Again, I warmed up this floaty summer maxi dress with brown tones for a cozy fall look.
Check out more photos & outfit details for this look here | Wearing White After Labor Day
Toned-down Tie Dye 7 of 21
An easy way to wear your fun summery dresses into fall is by adding a t-shirt layer under, a fun jacket over, and wearing browns and cognacs colors to warm up your fun summer prints.
Check out more photos & outfit details for this look here | Tie Dy Maxi with Jacket
From Maxi Dress to Skirt in Seconds 8 of 21
This simple black maxi skirt began as a kimono style maxi dress. But over time, it shortened in the wash and wasn't wearable with certain shoes. Since it had an elastic waistband already built in, I simply cut the top off and was able to continue wearing it as a skirt rather than sending it to Goodwill.
A black maxi skirt is easy to wear for all seasons. I warmed it up with brown accents and added a little pop with the bold black and white stripes. What you can't see are my heavy duty black tights underneath to keep me warm in the crisp fall breeze!
Check out more photos & outfit details for this look here | Maxi Skirt with Stripes and Sweater
See it here originally, as a dress | Black Kimono Style Caftan Maxi Dress
Add a Big Cozy Sweater 9 of 21
This is one of my favorite maxi dress for the mixed prints and feminine ruffles. To take it into the chillier months here I simply threw on a big cozy sweater and some boots and kept the soft feminine vibe.
Check out more photos & outfit details for this look here | Layered Floral Maxi with Oversized Sweater
Long Tunic & Blazer 10 of 21
This is another favorite maxi that was once a dress that I turned into a skirt and I wear it season after season for years now. Here I threw on a long sequined black tunic with a long black blazer and oxford flats for a casual dressed up look that kept me warm enough for chilly fall weather.
Check out more photos & outfit details for this look here | Pink Maxi Skirt with Black Sequin Tunic and Blazer
A Little Military 11 of 21
I love this long slinky bright blue jersey maxi for summer, and for fall, I added a cropped military style jacket with a studded belt to edge it up a bit.
Check out more photos & outfit details for this look here | Blue Jersey Maxi with Cropped Military Jacket
Layered T’s & Cardis 12 of 21
Another maxi dress-turned maxi skirt! I loved the print on this but hated the fit, so I made it a skirt and layered a t-shirt and long cardigan for an easy fall transition.
Check out more photos & outfit details for this look here | Printed Maxi Skirt that was a dress
See the original dress and find out how to easily DIY your Maxi Dress into A Maxi Skirt
Add a Blazer 13 of 21
More than anything, fall colors read fall even if the weather is still a bit too warm for layers. I added a light colored blazer in a warm hue and paired it with brown accessories to transition this button down maxi from summer to fall.
Check out more photos & outfit details for this look here | Button Up Maxi with a Blazer
Add a Little Leather 14 of 21
I love adding a little toughness to my pretty pink skirt with a vintage leather patchwork jacket and leather boots!
Check out more photos & outfit details for this look here | Leather Jacket with Maxi Skirt
Winter Wonderland 15 of 21
This is more winter than fall, but it was one of my FAVORITES and still applies. I simply layered a light neutral blouse with a cozy sweater and paired it with a vintage heavy maxi skirt and boots for a winter wonderland outfit I loved.
Check out more photos & outfit details for this look here | White Maxi Skirt with Sweater
Leather and Lace 16 of 21
Another fun and edgy look by adding a cropped leather jacket and leather boots to my favorite ruffled maxi dress.
Check out more photos & outfit details for this look here | Floral Ruffled Maxi Dress with Cropped Leather Jacket
Cozy in Cognac 17 of 21
Granted, this is a knit sweater maxi skirt and made for chillier months but the colors lend themselves to falls dropping leaves and I just loved it. You can see this same cognac corduroy blazer worn with my bright blue maxi and how different it looks here paired with a layered blouse and light sweater.
Check out more photos & outfit details for this look here | Chevron Maxi Skirt with Sweater and Cognac Blazer
All Layered Up! 18 of 21
A more fall look with the same vintage white maxi skirt, I added an oversized denim button down and an asymmetric hem sweater in toasty fall colors, belted and booted it and called it a day. This look reminded me of an 80's Ralph Lauren ad.
Check out more photos & outfit details for this look here | Vintage White Maxi Skirt with denim shirt
Layer Under 19 of 21
This look is stolen directly from the 90's... as is this dress that I've had in my closet since the decade. This alone is not warm enough for the chillier months, but think about layering cute t-shirts, short-sleeved and long, UNDER your maxi dresses for an extra layer of warm.
Check out more photos & outfit details for this look here | Dressed up Maxi with T-shirt under
Blazing Saddles 20 of 21
Again, my simple black maxi paired with a bright lavender blazer for physical warmth and brown tones to for a warm fall look.
Check out more photos & outfit details for this look here | Maxi with Bright Blazer
Pretty in Pink 21 of 21
Again, my soft pink maxi skirt but this time paired with a warm leopard print top, light cardigan and lace up flats for a cozy warm fall look.
Check out more photos & outfit details for this look here | Pink Maxi Skirt with Leopard