Shirts To Wear With Leggings For Short & Tall Women + The Best Leggings

Per usual, it is a constant struggle to find shirts to wear with leggings. It’s frustrating year round, but particularly during the cold season. Everyone loves leggings, everyone wants to wear leggings, and yet there is this constant drought of stylish shirts to wear with leggings. That’s why I am here to do the legwork for you. (Pun intended.) Below are all the client favorite shirts that are long enough to cover your crotch when you pair them with leggings, and all the specific leggings I recommend to pair with them. I even have you taller gals covered. (Yet another pun intended.)

Nic + Zoe To The Point Top

I love the statement sleeves on this knit top by Nic + Zoe. Pair with grey and brown leggings, or Liverpool’s pull-on skinny jeans for a legging look, that is not leggings. This shirt is available at NordstromSaks 5th Avenue (plus size), and Nic + Zoe.

Sizing Tip: Runs slightly big, but mostly true to size. As usual, I recommend ordering two sizes to compare. If you’re taller than 5′ 6″ it probably won’t cover your crotch, so pair it with skinny jeans instead.

1.State Multi-Way Cozy Tunic Top

shirts to wear with leggings

1.State $59 $35.40

This 1.State Multi-Way Cozy Tunic Top looks so expensive in person — I thought it was Theory at first. It fits and drapes beautifully, and even clients who hate bulk around their neck have been loving it. Pair with light grey and black leggings, or Liverpool’s pull-on skinny jeans. For tall women who need longer leggings, I recommend Long Tall Sally’s classic jersey leggings with a 34″ inseam.

Sizing Tip: Runs true to size and should cover the crotch of women up to 5′ 9″. If it doesn’t cover your crotch, pair with skinny jeans. For you tall drinks of water, here are skinny jeans with an inseam of 32″ or longer.

1.State Multi-Way Cozy Tunic Top

shirts to wear with leggings

1.State $59 $35.40

This is a different color of the 1.State Multi-Way Cozy Tunic Top above because I just had to show you this option as well. Pair with dark grey and black leggings, or Liverpool’s pull-on skinny jeans. For tall women who need longer leggings, I recommend Long Tall Sally’s classic jersey leggings with a 34″ inseam.

Sizing Tip: Runs true to size and should cover the crotch of women up to 5′ 9″. If it doesn’t cover your crotch, pair with skinny jeans. For you tall drinks of water, here are skinny jeans with an inseam of 32″ or longer.

Caslon Seam Detail V-Neck Tunic

shirts to wear with leggings

Caslon $69 $41.40

I adore this Caslon Seam Detail V-Neck Tunic. Finally, a Caslon sweater that doesn’t have drop sleeves! Drop sleeves are so unflattering on most women. This sweater is perfect! Pair with grey, black, and brown leggings, or Vince’s side-zip pants in dark green, or Liverpool’s pull-on skinny jeans.

Sizing Tip: Runs large. Order a size or two down. If you’re taller than 5′ 8″ it probably won’t cover your crotch, so pair it with skinny jeans instead. For you tall drinks of water, here are skinny jeans with an inseam of 32″ or longer.

Nic + Zoe Meadow Knit Top

The Nic + Zoe Meadow Knit Top is my all-time favorite of the shirts to wear with leggings. It is long, stylish, interesting, and pairs with so many different colors. You can wear it with brown, navy, black, and grey leggings, or Vince’s side-zip pants in dark green, or Liverpool’s pull-on skinny jeans. Wow. For tall women who need longer leggings, I recommend Long Tall Sally’s classic jersey leggings with a 34″ inseam. This top is available at Amazon and Nic + Zoe.

Sizing Tip: Runs true to size, and should cover the crotch of women up to 5′ 11″. If it doesn’t cover your crotch, pair with skinny jeans. For you tall drinks of water, here are skinny jeans with an inseam of 32″ or longer.

Lou & Grey Cozystitch V-Neck Sweater

shirts to wear with leggings

Lou & Grey $69.50

I adore this super comfortable cotton sweater. With its raglan sleeve and v-neck, the Lou & Grey Cozystitch V-Neck Sweater is so flattering. Pair with light grey leggings, and Liverpool’s pull-on skinny jeans. This sweater is available at Nordstrom and Lou & Grey.

Sizing Tip: Best for women under 5′ 6″. Runs true to size otherwise. If you’re taller than 5′ 5″, skip leggings with this top, and pair with skinny jeans. If it doesn’t cover your crotch, pair with skinny jeans. For you tall drinks of water, here are skinny jeans with an inseam of 32″ or longer.

Lou & Grey Stripe Plushfuzz Tunic Sweater

shirts to wear with leggings

Lou & Grey $69.50

I love the camel color of the stripe and the relaxed crew neck of the Lou & Grey Stripe Plushfuzz Tunic Sweater. Pair with brown leggingsVince side-zip dark green legging pants, or Liverpool’s pull-on skinny jeans. For tall women who need longer leggings, I recommend Long Tall Sally’s classic jersey leggings with a 34″ inseam. This sweater is available at Nordstrom and Lou & Grey.

Sizing Tip: Runs a little overused, but true to size, and should cover the crotch on women up to 5′ 10″. If it doesn’t cover your crotch, pair with skinny jeans. For you tall drinks of water, here are skinny jeans with an inseam of 32″ or longer.

Brochu Walker Levar Wool & Cashmere Sweater

I can’t wait to personally wear the Brochu Walker Levar Wool & Cashmere Sweater. It did not arrive in time for this post, so I can’t report on the feel, but Brochu Walker never disappoints me. Pair with brown, grey, navy and black leggings, or Liverpool’s pull-on skinny jeans. For tall women who need longer leggings, I recommend Long Tall Sally’s classic jersey leggings with a 34″ inseam.

Sizing Tip: True to size, but I would order a size down as well just in case. It should cover the crotch of women up to 5′ 9″. If it doesn’t cover your crotch, pair with skinny jeans. For you tall drinks of water, here are skinny jeans with an inseam of 32″ or longer.

Gap Softspun V-Neck Pullover Sweater Tunic

shirts to wear with leggings

Gap $44.95 $31

Everyone is loving this burgundy v-neck tunic. Pair the Gap Softspun V-Neck Pullover Sweater Tunic with black, brown, and grey leggings, or Liverpool’s pull-on skinny jeans.

Sizing Tip: Runs a little wide. You can order your true size or smaller depending on the fit you want. If you’re too all for this top to cover your crotch, pair with skinny jeans instead of leggings. For you tall drinks of water, here are skinny jeans with an inseam of 32″ or longer.

Neiman Marcus Shaker-Stitched Cashmere V-Neck Sweater

shirts to wear with leggings

Neiman Marcus $265 $129

If you have a relatively flat belly, the Neiman Marcus Shaker-Stitched Cashmere V-Neck Sweater is perfect for work and extremely flattering. Pair with brown, navy, and black leggings, or Liverpool’s pull-on skinny jeans.

Sizing Tip: Runs true to size and should cover the crotch of women up to 5′ 8″. If you’re too all for this top to cover your crotch, pair with skinny jeans instead of leggings. For you tall drinks of water, here are skinny jeans with an inseam of 32″ or longer.

Maison Jules Cotton V-Neck Tunic Sweater

I love that this light grey Maison Jules Cotton V-Neck Tunic Sweater does not have a drop sleeve, which makes it flattering for larger busted or wider shouldered women. Pair with grey and black leggings, or Liverpool’s pull-on skinny jeans.

Sizing Tip: Runs true to size and should cover the crotch of women up to 5′ 8″. If you’re too all for this top to cover your crotch, pair with skinny jeans instead of leggings. For you tall drinks of water, here are skinny jeans with an inseam of 32″ or longer.

Nic + Zoe Ease Tee

The Nic + Zoe Ease Tee is great for leggings, but totally boring unless you pair it with a long necklace, like this Stella + Ruby tassel necklace. This tee is available at NordstromZappos, and Nic + Zoe. Pair with brown, grey and Vince side-zip legging pants in dark green, or Liverpool’s pull-on skinny jeans.

Sizing Tip: Runs true to size and should cover the crotch of women up to 5′ 9″. If you’re too all for this top to cover your crotch, pair with skinny jeans instead of leggings. For you tall drinks of water, here are skinny jeans with an inseam of 32″ or longer.

Bailey 44 Hold Me Tight Houndstooth Check Tie Front Shirt

shirts to wear with leggings

Bailey 44 $228 $182.40

I adore this shirt! The Bailey 44 Hold Me Tight Houndstooth Check Tie Front Shirt is soft and so much more comfortable than most shirts to wear with leggings. Look at the sizing tips though before you order. Pair with black, Vince side-zip leggings pants in burgundy, and grey leggings, or Liverpool’s pull-on skinny jeans. This shirt is available at Nordstrom and Bloomingdale’s.

Sizing Tip: Runs very small. As a size 6, 5′ 4″ woman I needed a large. If you’re over 5′ 4″ it probably won’t cover your crotch, so pair with skinny jeans instead of leggings.

Amour Vert ‘Elena’ Roll Tab Sleeve Top

I love this uber soft top if you want a super casual, yet flattering legging look. Pair the Amour Vert ‘Elena’ Roll Tab Sleeve Top with brown or grey leggings, Vince side-zip legging pants in dark green, or Liverpool’s pull-on skinny jeans.

Sizing Tip: Runs big. Order a size or two down. To pair it with leggings, it is best for women under 5′ 6″. If you’re too all for this top to cover your crotch, pair with a burgundy, olive green or light-wash skinny jeans instead of leggings. For you tall drinks of water, here are skinny jeans with an inseam of 32″ or longer.

Halogen Relaxed V-Neck Cashmere Sweater

shirts to wear with leggings

Halogen $89 $58.90

Many women are too tall to wear the Halogen Relaxed V-Neck Cashmere Sweater with leggings, but it is perfect for my 5′ 4″ self. I recommend the teal or the lavender shade. Pair with black, brown and grey leggings, or Liverpool’s pull-on skinny jeans.

Sizing Tip: Runs hugely wide. Order two sizes down, but keep in mind that if you’re taller than 5′ 4″, it will be best with jeans, not leggings.

Nordstrom Signature Cotton Poplin Tunic

The Nordstrom Signature Cotton Poplin Tunic is fantastically flattering. For ladies 5’3″ and under, it works as a dress. For everyone else, it’s a perfect tunic. Pair with black, navy, light grey, Vince side-zip dark green legging pants, or Liverpool’s pull-on skinny jeans. For tall women who need longer leggings, I recommend Long Tall Sally’s classic jersey leggings with a 34″ inseam.

Sizing Tip: Runs true to size and should cover the crotch of all women.

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