Fall Outfits with Leggings

When the crisp fall air arrives and the leaves begin to change color, our style impulses tend towards cozy! Sweaters, scarves, boots, knits, warm socks, and leggings are autumn layering essentials. Fall signals a return to sophisticated silhouettes and put together outfits, but thankfully a pair of comfy, thick leggings can serve as the foundation of a perfectly layered outfit. Fall outfits with leggings will see you stylishly through a busy fall calendar filled with outings to pumpkin fields and apple orchards, getting the kids back to school, and long work days!


When fall hits full stride, plaid can be seen everywhere — from cozy flannels and menswear blazers to midi wool skirts and stylish coats. Venturing into tartan territory is not for the faint of heart, but if you’re bold enough to rock a pair of plaid leggings, you’ll discover they are infinitely more versatile than they seem at first blush.

Plaid became a wardrobe staple in the 1960s, although it dates all the way back to 16th century Scotland. This classic print has been passed from rustic lumberjacks to preppy co-eds to grunge rockers. Few prints in style history have been embraced by so many different groups.

On the preppy side of things, plaid can be paired with tailored pieces, blazers, and cozy knits. Pattern mixing with stripes is also an unexpected combo, if layered with solid hues, like a striped collared shirt worn under a navy knit pullover. Street style fall outfits with leggings tend to combine a bit of schoolyard prep with rocker edge, for a look that pulls the best from both worlds.

**Plaid Pairs Perfectly With Chunky Knit Scarves, Sweater Tunics, And Rich Fall Hues


Get the perfect fall outfits with plaid leggings when you check out our top three favorites here!

  • Flea Market

    Plaid leggings + belted tunic top + pearls + satchel bag + knee-high boots

    Where to wear: Look fly at the flea market when browsing for new wicker furniture!

  • Work

    Plaid leggings + oversized white button-up shirt + blazer + infinity scarf + Chelsea boots

    Where to wear: Going straight from work to parent-teacher conferences looking classic.

  • Pumpkin Picking

    Plaid leggings + sweater dress + oversized cardigan + saddle bag + rustic boots

    Where to wear: Fit in on the farm when you go for a pumpkin patch outing.

5 Mix & Match
Fall Essentials

1. Fall BootsBoots are one of the crucial building blocks of a fall outfit with leggings, and there are a few different essential styles every woman needs in her shoe closet. Moto boots lend an edgy vibe, while close-fitting ankle-high Chelsea boots are effortlessly modern. Buckles and fringe detailing are trendy, and cowboy boots pair well with rustic ensembles. Knee high boots look lovely worn over leggings and keep you warm on chilly days!

2. BlazerA tailored blazer belongs in every woman’s fall closet. A blazer can either look sleek and professional, or have a fun tomboy style, depending on how you wear it. A black blazer worn over a longer tank top for a fall outfits with leggings adds a sophisticated clean line for a polished ensemble.

3. Patterned ScarfScarves come to the rescue on windy days! From chevron zigzags to tribal prints, a patterned scarf adds visual interest in layered outfits. Besides the classic slip knot, fall scarves can be worn wrapped into a messy circle with the ends tucked in, braided in loose knots over a sweater if it’s of a more delicate material, or can glamorously hang free draped over your neck with both ends hanging down on warmer days.

4. Shift dressA great shift dress can go from creative meetings to craft cocktails, making it a day to night staple. A shift dress should have shape in the cut, so you don’t get lost in yards of fabric, but be loose enough to team up with leggings and structural coats for a perfect fall outfit with leggings.

5. Oversize CardiganSteal your husband’s cardigan or buy your own oversized piece for a super cute fall outfit with leggings. A black or grey cardigan pairs easily with everything in your closet, while a bold hue can liven up a monochrome ensemble. Wear it over slouchy dresses, tunics, and leggings.


When we think fall, we have idyllic images in mind: apple picking at an orchard or going for a walk among the changing leaves. As the temperatures dip, we do have to bundle up first! Layering is essential to putting together cozy fall outfit with leggings for all the season’s outings. Leggings are a transitional style staple, a must-have for staying warm. Patterned bottoms have been a favorite of fashion blogs, but loose harem pant and flare cut styles don’t always work off the runways. A pair of cute paisley leggings are a stylish way to incorporate patterns into a fall outfit!

Fall fashion is defined by warm, earthy hues like maroon, mustard yellow, deep brown, and emerald green. Mix and match these gorgeous fall hues in your layering pieces, and choose colors for outfit pairings that can be found in the paisley print of your choice.

If you are putting together a fall outfit with leggings with print or patterned leggings, but you want the style thermometer to read dressy, then add some elegant wardrobe pieces. A blazer or statement necklace, a peplum top, or an oversized crisp button-up can help keep you fashionable. Fall fashion tends to be more sophisticated, and structured pieces help elevate the casual look of leggings.

**Paisley Pairs Perfectly With Ruffled Tops, Rustic Boots, And Vintage-Inspired Accessories

5 Fall Layering Tips

1. Foundational CourseMastering the art of layering means starting at the foundation of the outfit, with the top and bottom. Leggings are just hands down cozier than skinny jeans, so they always top our pile of fall favorites. A maxi skirt can also look darling in a fall outfit with leggings. For the top, either a lightweight tee, button-up shirt, or long sleeve tunic blouse is ideal.

2. Shape UpOne of the pitfalls of layering is when it results in an all-over bulky shape. Staying cozy is the goal, but looking frumpy is not! This is why the slim fit of leggings is crucial in fall layering. Another way to create a chic shape is to consider the different lengths of your layered pieces. Add a pullover sweater or oversized cardigan in a rich autumn hue, and make sure that it is either shorter or longer than your bottom layer top. Try creating a waistline with a belt over a tunic or button-up shirt. Finally finish it off with a coat in a basic color like black, army green, or camel.

3. Bright BaublesJust because you’re getting all covered up, don’t forget the accessories! Jewel tones in statement necklaces add a pretty touch when peeking out beneath the layers of a fall outfit with leggings.

4. Totally TexturalAs much as you should consider the color and lengths in a layered outfit, if the fabrics are all the same, the look will fall flat. Mix up the textures for a more visually interesting ensemble. This is best achieved with varying the fabrics you choose, like mixing thick knits with light cotton or silk. Beyond fabrics, pretty details like ruffles and lace on a shirt hemline or a cute collar seen beneath a sweater create a more complex layered ensemble.

5. Always Add a ScarfThe quickest way to take a layered outfit to the highest levels of style? Scarves! Whether you choose a knit infinity scarf, a graphic silk or printed option, scarves are the greatest thing to look forward to as the colder weather arrives. Throwing on a big, soft pashmina is as close to the coziness of staying in bed while running errands you can possibly get.


Take the plunge with some of these adorable paisley fall legging outfits!

  • Apple Picking

    Paisley leggings + a sweater dress + tan wide-brimmed hat + knee high boots

    Where to wear: Apple picking at a local orchard & baking apple pie should be on every fall bucket list!

  • Reading Hour

    Paisley leggings + Peter Pan collar top + loose pullover sweater + loafers

    Where to wear: A children’s book reading hour at the local library is the perfect place to get comfy.

  • Weekend Getaway

    Paisley leggings + long sleeve tunic + knit cape + beanie + rustic cowboy boots

    Where to wear: Get away for a weekend at a cabin in the woods.


Indulging seasonal cravings like apple cider, pumpkin pie, and anything with cinnamon should be the first thing on your fall to-do list. The second is making sure there is a stack of printed leggings in your closet to mix and match for fall outfit with leggings!

Among the prints for fall, snakeskin is a glamorous standout. Exotic animal prints have moved from the province of resort wear to everyday ensembles. If you’re looking to try out a new trend without investing in major wardrobe pieces first, leggings are a great way to see how you can work the trend into your style. Snakeskin leggings can play a minimal part in a layered outfit, when paired with knee-high boots and sweater dresses, or they can be the centerpiece of a going out ensemble, with black pumps and a loose black chiffon top.

To look pretty in python, the first rule of thumb is to keep the rest of the outfit toned down with elegant, understated pieces. Edgy and sophisticated, snakeskin leggings pair best with casual pieces like grey pullovers and basic tops, and neutrals like black or cream, a grey or brown purse, and neutral boots or flats. A fun on-the-go pairing for snakeskin leggings is a graphic tee, thick black scarf, and cute athletic sneakers. One animal print in a fall outfit is enough though, so don’t choose a snakeskin purse or a leopard scarf as accessories.

**Snakeskin Pairs Perfectly With Sophisticated Accessories, Fall Boots, And Neutral Hues


Make snakeskin your fashion favorite when you explore our outfit ideas!

  • Sporting Events

    Snakeskin leggings + a long tunic top + military parka + Chelsea boots

    Where to wear: Cheer your kids on when they’re at a game! You’ll be scoring from the sidelines!

  • Dinner Parties

    Snakeskin leggings + oversized white tee + statement necklace + long cardigan + ballet flats

    Where to wear: Try a new look at an autumn dinner party.

  • A Night Out

    Snakeskin leggings + mini-black shift dress + cropped jacket + black pumps

    Where to wear: Look silky smooth for some Friday night cocktails after a day at work!


Certain fashion trends evolve over time. While there is nothing new about snakeskin prints per se, since they were in vogue all the way back in the 1920s, the colorful snakeskin is a bold new take on the serpentine look. The print has appeared in a swath of bright colors, adorning everything from blouses and printed bottoms to outerwear. Colorful snakeskin is trend-forward and adds flair to any outfit.

Monochrome SnakeskinBlack and white is a sleek way to play it safe with the snakeskin trend. Monochrome snakeskin leggings act as the foundation of a chic black and white outfit, since they allow you to add print within the monochrome scheme. For casual weekends, add a white button-up or long white blouse and cropped black sweater.

Natural SnakeskinSnakeskin prints in organic hues, like creams, tans, and browns, have a more bohemian feel that’s perfect for fall outfits. Snakeskin leggings in natural hues look stunning with rich fall shades, like dark berry and forest green.


At White Plum, you can find all the leggings you’re looking for and advice on how to wear them. Shop our collections today and check out our top tips for wearing spring, summer, winter, and fall outfits with leggings.