17 Fall Outfits Leggings That Solve Your Biggest Leggings Problems
Every fall, my inbox fills with the same leggings questions. “Can I wear leggings to work?” “What do I wear on top so I don’t feel exposed?” “How do I make them look less like I just came from the gym?” And my favorite: “Is it still okay to wear leggings as pants?”
Here’s my honest answer to that last one: yes, if you style them well. Leggings are comfortable, warm and easy to move in, which is exactly what most of us need on a busy fall day. The trick is choosing the right leggings and the right pieces to go with them.
So instead of giving you another random list of outfits, I’ve organized these 17 fall leggings outfits around the six problems readers ask me about most. Each section solves one problem with two or three outfits.
For every outfit, I’ll tell you the leggings to use, because black cotton leggings and faux leather leggings are completely different animals, and the coverage level of the top: full (covers your bottom), hip, or waist. That way you can choose what you’re comfortable with.
At the end, you’ll find the see-through test every pair should pass, a leggings fabric guide, leggings vs. tights vs. jeggings, length tips for petite and tall women, and how to make your leggings last.
Let’s solve some problems.
Problem 1: “I Feel Too Exposed in Leggings”
The most common worry by far, and the easiest to fix.
1. Tunic Sweater and Knee Boots
A long, cozy tunic sweater that falls to mid-thigh, black leggings and knee-high boots. It’s the classic fall leggings outfit for a reason: warm, covered and comfortable all day.
Choose a tunic in a fall shade like oatmeal, camel, forest green or burgundy, and push the sleeves up a little so it doesn’t swallow you.
Leggings to use: thick black cotton-blend or ponte leggings
Coverage: full
2. Oversized Shirt and a Belt
A long, oversized button-down shirt, like a chambray, flannel or crisp white poplin, belted at the waist over black leggings, with ankle boots. The belt adds shape, and the long shirttails give you coverage.
Leggings to use: matte black leggings
Coverage: full
Tip: Roll the sleeves twice and leave the top two buttons undone for a relaxed look.
3. Duster Cardigan and a Fitted Tee
A fitted long-sleeve tee tucked loosely into high-waisted leggings, with a long duster cardigan that falls to your knees, and white sneakers. The cardigan creates a long vertical line that’s flattering on everyone.
Leggings to use: high-waisted black leggings
Coverage: full (with the cardigan on)
Problem 2: “I Need to Look Professional”
Yes, leggings can go to the office, if you choose wisely.
4. Ponte Leggings, Silk Blouse and Long Blazer
Ponte leggings are made from a thick, smooth knit fabric that looks more like tailored trousers than gym wear. Pair them with a silk blouse and a long blazer that covers your hips, finished with loafers or pointed flats.
It’s comfortable enough to sit in all day, and polished enough for meetings.
Leggings to use: black or navy ponte leggings
Coverage: full (with the blazer)
5. Sweater Dress Over Leggings
A fine-knit sweater dress that ends just above the knee, worn over black leggings with pointed flats or low heeled ankle boots. It looks like a dress-and-tights outfit, but feels warmer and more comfortable.
Leggings to use: thick matte black leggings
Coverage: full
Tip: Choose a dress in a solid color, like charcoal, burgundy or camel, for the most professional look.
6. Turtleneck and a Sleeveless Long Vest
A fitted black turtleneck with ponte leggings, a long sleeveless vest or sleeveless coat in camel or gray, and loafers. The long vest adds structure and coverage without the bulk of a coat.
Leggings to use: black ponte leggings
Coverage: full (with the vest)
Problem 3: “It’s Freezing Out There”
Leggings can be surprisingly warm, when you choose the right pair.
7. Fleece-Lined Leggings, Chunky Sweater and Puffer
Fleece-lined leggings are one of the best inventions for cold weather. They look like normal leggings outside, but feel soft and warm inside. Pair them with a chunky knit sweater, a puffer jacket and warm, waterproof boots.
Leggings to use: fleece-lined black leggings
Coverage: hip (sweater) to full (puffer)
8. Shearling Jacket and Shearling Boots
Fleece-lined leggings, a long cream knit, a faux shearling jacket and shearling-lined boots. It’s cozy from head to toe, and ideal for autumn walks, school runs and cold weekend errands.
Leggings to use: fleece-lined leggings in black or chocolate
Coverage: hip
9. Leggings Under a Midi Skirt or Dress
Here’s a trick I use on the coldest days: wear leggings under a midi skirt or dress. A knit midi skirt with black leggings, a tucked-in sweater and ankle boots looks polished, and it’s much warmer than tights.
Leggings to use: thin black leggings (thick ones can bunch under skirts)
Coverage: full
Tip: Choose ankle-length leggings so they don’t wrinkle at your boots.
Problem 4: “I’m Going Straight From the Gym to Brunch”
Athleisure that actually looks put together.
10. Flared Leggings and a Denim Jacket
Flared leggings, sometimes called yoga flares, are fitted through the thigh and flare out below the knee. Pair them with a cropped sweatshirt, an oversized denim jacket and chunky white sneakers.
The flare makes them look more like trousers, so you’ll feel dressed for brunch.
Leggings to use: black flared leggings
Coverage: waist
11. Matching Set, Half-Zip and Belt Bag
A matching workout set, with a sports bra and leggings in the same color, plus a half-zip pullover, a belt bag worn across your body and clean sneakers. Wearing matching colors makes it look intentional and stylish.
Leggings to use: matching sets in olive, mocha, navy or charcoal
Coverage: waist to hip
12. Oversized Sweatshirt and a Puffer Vest
High-waisted leggings with an oversized crewneck sweatshirt, a puffer vest, crew socks, sneakers and a baseball cap. It’s sporty, comfy and practical for chilly post-workout coffee runs.
Leggings to use: high-waisted black leggings
Coverage: hip
Problem 5: “I’m So Tired of Black Leggings”
Color and texture make leggings feel brand new.
13. Chocolate Leggings and Tonal Knits
Chocolate brown leggings, a cream chunky knit sweater and tan suede boots. Tonal outfits in warm browns and creams look soft, expensive and very fall.
Leggings to use: chocolate brown ponte or matte leggings
Coverage: hip
Tip: Brown is more forgiving than black. It shows less lint and looks softer next to autumn colors.
14. Burgundy Ribbed Leggings Set and a Camel Coat
Burgundy ribbed leggings with a matching ribbed long-sleeve top, and a long camel coat on top. Loafers or sneakers finish the look. The ribbed texture makes it look like a cozy knit set, not workout wear.
Leggings to use: ribbed leggings in burgundy, olive or navy
Coverage: waist (full with the coat)
Problem 6: “I Want to Wear Leggings to Dinner”
Leggings can absolutely be dressy.
15. Faux Leather Leggings and an Oversized Cashmere Sweater
Faux leather leggings are the dressiest leggings you can own. Pair them with an oversized cashmere or soft knit sweater and heeled ankle boots. The mix of soft and sleek looks effortlessly chic for dinner or drinks.
Leggings to use: matte black faux leather leggings
Coverage: hip
16. Faux Leather Leggings, Silky Blouse and Blazer
Faux leather leggings with a silky blouse and a tailored blazer, finished with pointed pumps or heeled boots. It’s polished, confident and perfect for a special evening.
Leggings to use: black faux leather leggings
Coverage: hip (with the blazer)
17. Stirrup Leggings and Pointed Pumps
Stirrup leggings, with a strap that goes under your foot, are having a comeback. Wear them with a long, fine-knit sweater and pointed pumps or heeled mules, so the stirrup shows. It’s elegant, a little retro and very flattering.
Leggings to use: black stirrup leggings in a thick fabric
Coverage: full
Tip: Stirrup leggings look best with shoes that show the arch of your foot, like pumps, mules or ballet flats.
The See-Through Test
Before you buy (or wear) any pair of leggings, do the squat test. In good light, stand in front of a mirror, bend forward or squat, and look over your shoulder. If you can see your skin or underwear through the fabric, the leggings are too thin to wear as pants.
Thicker fabrics, darker colors and good-quality blends pass this test much more easily. Thin, cheap leggings almost never do.
The Leggings Fabric Guide
Not all leggings are made the same. Here’s a quick guide:
Cotton blend: soft and breathable, great for everyday wear. Choose thick ones to avoid see-through fabric.
Nylon and spandex: smooth, stretchy and supportive. Ideal for workouts and athleisure.
Ponte: thick, smooth knit with structure. The best choice for work and dressier outfits.
Fleece-lined: soft and warm on the inside. Perfect for cold weather.
Ribbed: textured and cozy, looks more like knitwear than workout wear.
Faux leather: sleek and dressy. Great for evenings and dinners.
Leggings, Tights or Jeggings?
These three get confused all the time:
- Leggings are opaque, cover your legs completely and are usually thick enough to wear as pants.
- Tights are thinner, usually sheer or semi-opaque, and cover your feet. They’re worn under skirts and dresses.
- Jeggings look like skinny jeans, often with pockets and a denim print, but feel like leggings.
Length Tips for Petite and Tall Women
Petite: Leggings that bunch at the ankle make your legs look shorter. Choose 7/8 or ankle-length leggings, or look for petite sizes. Match your leggings to your shoes to create a longer line.
Tall: Standard leggings can end too high on the ankle. Look for “tall” or “long” lengths, or embrace 7/8 leggings with ankle boots.
Everyone: High-waisted leggings are more flattering and comfortable for most people, because they smooth your middle and don’t slip down.
Where Leggings Work, and Where They Don’t
Styled well, leggings are fine for work (in many offices), errands, travel, brunch, casual dinners and school runs. But for formal events, job interviews in traditional industries, weddings and funerals, choose trousers, skirts or dresses instead.
If you’re unsure about your workplace, choose ponte leggings with a long blazer or sweater dress. They look so much like tailored trousers that few people will notice.
How to Make Your Leggings Last
- Wash inside out in cold water to prevent pilling and fading.
- Skip fabric softener. It can break down stretchy fibers over time.
- Air dry whenever possible. Heat from the dryer weakens elastic and can make leggings baggy.
- Wash separately from towels, which create lint and cause pilling.
- Rotate your pairs, so each one gets time to recover its shape.
Frequently Asked Questions
Can leggings be worn as pants?
Yes, if they’re thick, opaque and well-fitting. Pair them with longer tops, sweaters or jackets for a more polished look.
What shoes go with leggings in fall?
Ankle boots, knee-high boots, loafers, sneakers and ballet flats all work beautifully. Choose waterproof or shearling-lined boots for cold, wet days.
Can I wear leggings to work?
In many workplaces, yes. Choose ponte leggings, and pair them with a long blazer, sweater dress or tunic. Avoid workout leggings for the office.
What top should I wear with leggings?
Tunics, long sweaters, oversized shirts, sweater dresses and long cardigans give full coverage. For a more casual look, try sweatshirts or cropped tops with a longer jacket.
Comfort That Looks Put Together
Leggings don’t have to mean you’ve given up on getting dressed. With the right fabric, the right coverage and a few thoughtful pieces, they can be warm, professional, sporty or even dressy enough for dinner.
Think about which problem you face most, whether it’s feeling exposed, the cold or looking professional, and start with one of those outfits this week.
What’s your biggest leggings challenge? Tell me in the comments, and I might style it for you in a future post.
