53 Shirts To Wear With Leggings And Boots This Fall (2024)

Inside: 53 shirts to wear with leggings and boots this fall.

Each season comes with new challenges and new fun styles to bring back out of the depths of your closet. In the fall, we break out the leggings and the boots of all heights and styles and get ready to get cozy in our favorite pairings.

And every year, the way we pair and style these pieces in these seasons change, just a little. So every fall I’m constantly trying to figure out the coolest way to still wear over the knee boots this year.

Something that changes the most about fall fashion is the style of tops, sweaters, and scarves.

About five years ago, a minimal cropped sweater with a bulky blanket scarf was the absolute hottest trend. Now, not so much.

So what is trending as far as tops go in the fall of 2022? Great question.

I’ve broken it down and found some inspiration for you to see what’s trending this fall!

What Shirt Styles Are Best With Leggings?

The best tops to wear with leggings depend a lot on your personal style. Some prefer to wear them more conservatively and some don’t really care about the coverage.

On the more conservative side:

Oversized Sweaters – Personally, most of my sweaters are oversized anyway. When it comes to the cold weather season, I want all the oversized and cozy vibes. So whether I’m trying to fit more of a conservative vibe at the time or not, I’m all covered up in an oversized sweater.

Oversized Tees – I have one extreme or the other when it comes to Tee shirts– Three sizes too big or a tiny crop. So I love pairing a simple basic oversized tee with leggings and cool leather boots. It’s an outfit full of basics but it really hits the spot!

Button Downs – A longer button down will always be a classy look, and ready for anything. Big button down shirts are trendy right now so they’re cool to wear out and about on the streets or wear to work when paired with the right leggings and boots combination.

Longer Jackets – If your shirt isn’t as long as you want it to be to cover up everything it needs to, a long jacket is a great layering piece to add to the fit. Amy green cargo jacket, denim jacket, or a loose cardigan are always wins for this layer.

If this isn’t a major priority to you, you can mix in some crop tops and cropped sweaters.

What Are Trending Colors In 2022

We are loving color in 2022! And that’s a fact. Actually it’s true of every year around here, if I’m being honest.

There are three major trending colors that range from beautifully subtle colors to bold and bright. Wherever you are on the scale, there’s a 2022 color for you.

These are some of my own favorite colors, so I love that they’re trending! I’m so ready to snag a sweater or a cozy long sleeve in each of them.

The colors trending right now are Kelly Green, Fuschia, and Periwinkle.

Periwinkle is a subtle blue, super similar to lavender. If you feel like you’re not ready to jump into the bright pink fuschia, this is the move for you.

Kelly green is my favorite one to see in the trend cycle. Greens are so fun to play with because it can be a part of the neutral family or the color family so easily, and when you play each shade to its strength, it can be a beautiful combination. Kelly green is so bold while still playing to the natural elements, it’s the perfect color to play with this year.

What Boots Are In Style To Pair With Leggings?

Realistically, you can wear any boots with leggings.

However, the taller the boot, the more flattering on your leg. I’m not just talking about over the knee or knee highs, though they are stunning, even the taller ankle boots or the half-calf height boots.

I know that not everyone’s calves agree with the tall boot trend. I used to sell shoes at a major department store and all fall and winter long I would have customers looking for the perfect riding boots or over the knee boots and finding it in the right foot size with a wide calf was a challenge for sure. So if this is you, you’re definitely not alone, but the tall boot trend can still work for you!

Mid calf boots are super cool right now, whether they’re heeled booties, combat style, or western, they’re trendy and will work perfect for any style with leggings!

What To Wear With Leggings

We’ve done a little bit of a deep dive on this already, but here are some examples for you to follow!

From sweaters to jackets to crop tops, here are some of my personal favorite outfit ideas with leggings and boots.

1. Sweater And Shacket
2. Button Down
3. Combats And Jacket
4. Teddy Coat
5. Sweater Vest
6. Minimalist Sweater
7. Blazer
8. Teddy Crop
9. Quilted Jacket
10. Large Plaid

Cute Tops For Fall

Fall tops are some of my favorites, because I am personally obsessed with layers and layering pieces. A little knit crop top over a fitted long sleeve is my favorite duo!

The creativity that’s allowed when you can play with layers in cooler weather is so fun, so find some fun layers to play with and have fun creating your own perfect shirts with leggings & boots combo for your fall wardrobe.

11. Green Knits
12. Fuchsia Blouse
13. Button Down
14. Casual Golf Top
15. Periwinkle Sweater
16. Knit Top
17. Tan Sweater
18. Casual Tee
19. Free People Mock Neck
20. Long Sleeve Blouse
21. Polo Sweater
22. Preppy Sweater

Casual Leggings And Boots Outfits

These kinds of outfits can be super dressed up or super dressed down. If you need some casual vibes, here is some inspo for you!

23. Graphic Tee
24. Sublime Crewneck
25. Flannel And Beanie
26. Gray Flannel
27. Graphic And Pea Coat
28. Vintage Sweatshirt
29. Layered Graphic Tee
30. Pea Coat
31. Turtleneck Sweater
32. Platform Chelsea

Dressy Outfits

And here are the dressier options of leggings and boots outfits! Whether you’re heading out to brunch, dinner, or work, here are some cute shirts to wear with leggings and boots outfit inspiration I’ve tried that I’m sure you’ll love.

33. Button Up
34. Blazer
35. Striped Shirt
36. Plaid Blazer
37. Striped Sweater
38. Layered Pink Sweater
39. Motto Jacket
40. Tan Coat
41. Knee Highs
42. Long Cardi
43. Open Toe Booties

With Ankle Boots

Ankle boots can be hard because of the proportions, but they’re so cute and easy to make work if you know how to play it!

If you’re more eclectic or classy, here are some of the cutest ways to wear ankle boots with leggings.

44. Longer Sweater
45. Suede
46. Motto Chelseas
47. Gray Layers
48. Plaid Shacket
49. Snake Print
50. Browns
51. Combats
52. Winter Layers
53. 3 Ways

The fall pairings in theory should be super easy– stay warm but not too warm if it’s not too cold yet. That’s it.

But when boot and top trends are constantly changing each year and each season, and it’s cool to pair things up a little differently than we used to, it’s no brainer that it can get a little challenging every year!

But my rule of thumb when I really start to just get lost in all of the styling questions is to just throw on a light sweater and be good to go. Different tops create different styles and illusions, so working strictly with trends can be a little tricky because not everything looks the same on every body type. So find what works for you and find this year’s trend that works.

As far as colors go, brown boots are really hot this year. Check out this entire post about wearing brown boots this season.

I'm Victoria, I believe in style with a smile... because fashion should be fun! I'm a stylist with 15 years in the home and design online industry.