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. There are only a small selection of lengthy tops for these notoriously comfortable “pants,” and only a few of them are truly chic. The rest are too casual or are theme-oriented tunics and balloon blouses. That’s why I am here to do the legwork for you. (Pun intended.) Below are all my client-favorite shirts to wear with leggings that are long enough to cover your crotch, and all the specific leggings I recommend to pair with them. I even have you taller gals covered. (Yet another pun intended.)

Rock Flower Paper Red Crinkle Tunic

This 100% cotton lightweight tunic by Rock Flower Paper in a crinkle material will work year round if you’re in San Diego. Pair with navy, black or brown leggings and flats.

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 Nordstrom.

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

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. It’s one of my favorite shirts to wear with leggings. Pair it 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

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

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.

Lou & Grey Cozystitch V-Neck Sweater

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.

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

I love the camel color of the stripe and the relaxed crew neck of the Lou & Grey Stripe Plushfuzz Tunic Sweater. Pair with brown leggings, 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. This sweater is available at Nordstrom.

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

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

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 a great shirt for leggings, but totally boring unless you pair it with a long necklace, like this Stella + Ruby tassel necklace. This tee is available at Nordstrom, Zappos, 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 For Leggings

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 long 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

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 to pair with leggings. Wear it 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.

DVF Keyhole Print Silk Blouse

This DVF Keyhole Print Silk Blouse offers the perfect floaty length to give leggings a fresh breezy look.

Sizing Tip: Fits true to size.

Lewit Pleat Detail Cotton Blouse

This Lewit Pleat Detail Cotton Blouse is one of my favorite long shirts to wear with leggings. For the more relaxed environment, it can be paired with leggings and pointed toe flats for work.

Sizing Tip: Fits true to size.

Eileen Fisher 3/4 Sleeve Jersey Tunic

This Eileen Fisher 3/4 Sleeve Jersey Tunic is one of the best shirts to wear with leggings for a more casual look. Great for hiding a belly—without looking like you are hiding. It looks much better in person by the way.

Sizing Tip: Runs very large. Order a size or two down.

Free People Sunset Dreams Ruffle Top

This Free People Sunset Dreams Ruffle Top is fabulous for a leggings-with-booties look on a somewhat chilly day. I mention this because you can’t wear a jacket over it. I recommend a scarf if you’re cold.

Sizing Tip: Runs one or even two sizes big.

Alice + Olivia Shirts To Wear With Leggings

Another great option for a work look in a more creative work environment. This Alice + Olivia Toro Embroidered Tie Sleeve Blouse is only long enough for leggings if you’re shorter than 5′9″.

Sizing Tip: Runs small. Order a size up.

Lafayette 148 New York Karleya Print Silk Blouse

Lafayette does it again. This Lafayette 148 New York Karleya Print Silk Blouse is perfect with black or green leggings for work or play.

Sizing Tip: Runs about one size too big. Order two sizes to compare.

Theory Fluid Silk Georgette Top

This Theory Fluid Silk Georgette Top is a great shirt to wear with leggings for a going-out look. Pair it with grey leggings and heels. Add a long coat if you’re cold. For an edgier look pair the top with black leather leggings and suede boots. I don’t usually recommend an all black look unless we mix textures like we are doing here with silk, leather, and suede. As a side note, I also like mixing black lace with black leather.

Sizing Tip: Theory usual runs small, but this one had a bit of room. I recommend you order your usual size as well as a size up to compare.

Lafayette 148 New York Ruthie Silk Blouse

This Lafayette 148 New York Ruthie Silk Blouse is a real client favorite shirt to wear with leggings — and other items. Pair with a long necklace like Anna Beck’s gold pendant necklace, and wear for work or play with brown or black leggings. Keep in mind, you can also tuck this into a-line skirts. I recently had a client tuck it into this fabulous black leather skirt by Lewit.

Sizing Tip: Runs about one size too big.

Eileen Fisher Jersey Handkerchief Hem Tunic

Another more casual look, the Eileen Fisher Jersey Handkerchief Hem Tunic is a great shirt for lounging in leggings, while still looking fresh.

Sizing Tip: Runs very large. Order a size or two down.

Madewell Long Shirts For Leggings

This Madewell Button Down Tunic Shirt is great for navy leggings. Works for both casual and some work environments.

Sizing Tip: Runs true to size.

Halogen Side Ruched Top

This Halogen Side Ruched Top is an easy choice with its chic side ruching drawstring to jazz up those leggings.

Sizing Tip: Fits true to size.

This post is sponsored by Nakturnal.