Wowza, this post took some time! It’s been a HUGE request though so I’m so happy to have this done! Today I’m sharing 40 ways to style leggings. Yep, that’s right, FORTY ways! So, technically, this post could have you wearing leggings for an entire month…plus, ten days! Ha!
In the majority of these images I am wearing the Spanx Faux Leather Leggings, but in some I’m wearing others. You can easily replicate these looks with whichever leggings you prefer to wear. If the items I’m wearing are still in stock, I’ve linked them below. Also, this may be a good post to bookmark or add to your Pinterest because I’ll continue to add to this post in the future.
PSA: You’ll notice that in the majority of these outfits, I’m either wearing a long sleeve white tee, a sleeveless white tee, or a white tunic blouse…each of these have the length to cover you booty!
Alrighty, let’s dive in…
UPDATED: 10 NEW WAYS HAVE BEEN ADDED TO THIS POST!
Tunic // Denim Jacket (Similar HERE) // Leggings // Wedge sneakers (go up half a size)
Jen: Leggings // Top // Denim Jacket // Shoes | Remi: Jacket // Shoes // Tunic
Leggings (similar HERE) // Top (size up one) // Sneakers // Jacket
Leggings // Gladiator Booties // Top (size small) // Chambray Top
Sweater (sold out, similar HERE) // Leggings // Boots
Tunic // Vest // Leggings // Sneakers
Tunic // Vest // Leggings // Boots // Socks // Bracelets
Sweatshirt // Leggings // Slippers
Vest // Tee // Leggings // Boots
Vest // Tee (size up one) // Moto Leggings // Sneakers
Coat // Tunic // Leggings // Sneakers
Sweater // Chambray Top // Leggings // Boots
Tunic // Vest // Leggings // Sneakers
Cap //Sunglasses // Tunic // Vest //Leggings // Sneakers
Sweater // Scarf // Leggings // Boots // Hat
Camo Sweater // Mustard Top //Leggings
Leggings // My Hunter Boots / Remi’s Hunter Boots // My Sweater / Remi’s Sweater
Black Top // Similar Vest // Leggings // $20 Rose Gold Sneakers
Sweater // Leggings // Wedge Sneakers (size UP half a size)
Amazon Tunic // Boots (size down!) // Scarf // Leggings // Sunglasses
Sweater (wearing xs) // Leggings // Boots // Remi’s Dress // Remi’s Boots
My Leggings / Remi’s Leggings // My Boots / Remi’s Boots // My Jackets / Remi’s Jacket
Leggings // My Boots / Remi’s Boot // My Sweater / Remi’s Sweater
This $27 tunic comes in a ton of colors and it PERFECT for layering with sweaters when you need a little more length! It runs a little big so if you’re between sizes, go down. It’s available HERE.
Other items shown: Leggings // Boots (on SALE) // Sweater
Same tunic as above // Similar Boots // Vest // Bag // Leggings
Same tunic as above // Leggings // Pumps // Trench Coat
Leggings // Booties // White Tee (size small) // Mustard Sweater (xs)
Leggings // White Tee (size small) // Ugg Boots // Similar Cardigan // Bag
White Tee // Leggings (sold out) // Similar Plaid Top // Adidas
Moto Jacket // Leggings // Tank // Wedge Sneakers (go up half a size)
Moto Jacket // Leggings // Tee // Adidas
Tank // Cardigan (50% OFF today only) // Leggings // Flats
Striped Tee (size up one) // Leggings // Jacket
Same top as above // Similar Jacket // Leggings // Wedges Sneakers (go up half a size)
Same top as above // Vest // Leggings // Wedge Sneakers
Tunic Top (if between sizes, go down) // Booties // Bag // Leggings
Jacket (xs, other colors available) // Leggings // Booties // White Tee (size small)
Sweater (size xs) // Leggings // Boots (Similar option HERE)
Leggings // Tank // Green Top // Adidas
Nikes // Sweater // White Tee // Bralette // Leggings
Cardigan (xs) // White Tank // Leggings // Booties
Tunic (size small) // Wedge Sneakers (go up half a size) // Leggings // Green Jacket
Leggings // Tunic // Scarf // Adidas
Striped Tee // Sweater // Ugg Boots // Bag // Leggings
Hunter Boots // Leggings // Vest // Similar Tee
Sweater // White Tee // Adidas
Cardigan // Tank // Flats // Bag // Earrings // Leggings
Sweater // Leggings // Wedge Sneakers (go up half a size)
Striped Tee // Similar Sweater // Leggings // Ugg Boots
Leggings // Flats // Mustard Top (size small) // Chambray Top
Sweater (sold out) // Boots (SO COMFY)
Cardigan (I LOVE this) // Slippers // Leggings // Tank
Sweater (wearing xs) // Boots // Similar Boots // Leggings
Sweater (xs) // Leggings // Adidas
Chambray Top (this one is a little too short for leggings) // Vest // Leggings // Flats
Tunic (xs) // Leggings // Miller Sandals (color: sand)
Same tunic as a above // Vest // Boots // Similar Boots
Same tunic as a above // Tank // Wedge Sneakers (go up half a size) // Leggings
Tank // Cardigan // Leggings // Flats
Sweater // Leggings // Wedge Sneakers (go up half a size)
I LOVE this sweater!! // Tall Boots (similar boots) // Leopard Booties
Sweater // White Tee // Leggings // Adidas
Tank // Leggings // Adidas // Similar Jacket // Hat
Whew! Anyone make it all the way down? I really hope this post was helpful. Again, I’ll try to update it regularly as I continue to wear/style leggings. Also, if you’re looking for a pair of faux leather leggings, but don’t want to pay for the Spanx, Express has an option HERE and Target has an option HERE (size down one in these). Both have great reviews!
You can find a FULL list of weekend sales HERE.
xo, Jen
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Wowza! Thanks for doing this. I’ll be sure to reference back to this post everytime I need a leggings outfit! You’re awesome 😁
I’m SO glad this post is helpful! Thank you!!!!
Could u tell us who the make is for the checkered purse?
Amen!! Jennifer is the BEST!
For up to date 2019 leggings and best deals please go to
only-options.myshopify.com
This is EXACTLY what I’ve been needing!! I tried to search ideas on Pinterest yesterday but didn’t have much luck. Thank you!!
YAY!!! I’m so happy that it’s helpful!!
This was an awesome post! I live in leggings at work I’m a special Ed teacher and I’m constantly moving majority of these outfits would work! Any stores you know of that would have the long white/black tops,tanks,tunics? I’m tall so it’s hard to find something that covers my “assets “ lol
Thank you for doing this! I loved looking at all the different styles!
Thank you so much! This is so helpful!
This is so perfect! Thank you so much! I am beyond excited to start styling 🙂
This is awesome. I would love to see more ways of staying the wardrobe. I often get in a rut and end up just wearing things the same way.
I meant styling not staying 🤦🏼♀️
I definitely plan to do similar posts in the future! 🙂
This is everything and a great resource to go back to over and over again!!! The weather is finally cooling down here in Northern California and I can’t wait to reproduce some of these looks!
I’m so glad it’s helpful! I’m hoping the weather will start to cool down here; I’m ready for leggings and cozy sweaters! 🙂
This is great! You’re the best.
Exactly what I needed and was hoping for!!!
LOVE this post and all the links for the pieces!!!
Ugh!!! So darn cute and versatile, but I just CANNOT get myself to wear leggings! I must have some sort of malfunction here. I guess I feel you have cute,thin little legs, while I have tree trunks for legs 🤣. Maybe one day I’ll get the courage to actually wear some because these outfits are so fantastic, I love them all!! Thanks again!
♡, Maggie
You just made all my Wardrobe dreams come true with this post!! Thank you taking the time to do this ❤️❤️❤️
Aw!!! Yay!!!
GIRL!!! You OUTDID yourself with this post! This is absolutely amazing and I was sweating just looking at all of the different outfit changes! Seriously so helpful! Thanks, Jen!
Thank you, Niki!!
Wow!! Awesome post- I got so many great ideas for fall! I love every single way you styled your leggings!
Thank you so much!!!
I wish I could save this whole post!! All your outfits are great!! You are adorable & real & I soooo enjoy your blog!! ❤️
I would love to know which T-shirt or long sleeve shirts that you wear UNDER the sweaters are the longest. I’m 5’8/5’9 and I don’t want to order shirts that are on the shorter side in me. Shirts that I could layer under sweaters or hoodies and wear with leggings that are long for a taller girl. Thanks!!!
Hi Kristina,
I am about your height and have a hard time with longer shirts too. I always look for anything that says tunic in the description. The Nordstrom top she is wearing in the first few looks is super long. I have it in a couple of colors and it definitely covers my booty. Size down though. I am usually a size S and the XS is plenty roomy for me. I also like this lightweight sweatshirts from Amazon. They are the perfect legging length and could definitely be layered in colder weather. https://www.amazon.com/gp/product/B076M1NX4Z/ref=oh_aui_detailpage_o09_s01?ie=UTF8&psc=1
Holy crap! This post is thorough! You gave me so many ideas (and also just made me order about 5 new sweaters!)
Bookmarking this. Since I’m having a baby in November, I’m going to be wearing a certain leggings for a while to help with the belly situation. Having these outfit ideas will help me tremendously so I don’t have to think so much 😉
Allison
http://clementschronicles.com
This post is amazing!! Thank you!
How do the spanx leggings fit? True to size?
Yes, they’re TTS and SUCH great quality!!
This is the greatest leggings post of all time. You always have such great style and you totally knocked it out of the park with this one!! Thank you so much!!!
Thank you soooo much!!!
SO perfect for my last month of pregnancy! Thanks!
have you had an issue with the aerie joggers and the pockets coming unsewn? I own 2 pair and its happened on both but it was a while ago, so wondering if its worth trying again.
Love them all! Thank you!
This post is so cool! But can we talk about your precious dog??? Am i the only who notices him/she either on the chair or blending in with the rug??? Lol too cute
Wow!!!! This was the best post! Now I have many ways to wear my leggings! Thank you for all your hard work on this!!! Awesome sauce!!! 😗
Umm ok all my outfits are going to be created based on this post…thank you so much!
This post 🙏🙌 is EVERYTHING!! Thank you!!
I LOVE this post! I’ll be looking back on this one many more times to come. What’s better than wearing leggings everyday?! Love it.
Thanks Jen💜
I love this post! I’ve referenced it at least 4 times already!! Your a life saver!!
Are the uggs the sort or tall style?
Short! 🙂
I just wanted to hop on here and let you know this is awesome! I am so grateful for the time and energy you put into all of your posts, especially this one! Happy Thanksgiving!
Thank you so much!!
Would anyone make recommendations on length? I’m 5’7” & not sure whether to order regular or tall leggings. Mostly wear booties. Great post!
I am still going back to this post!! Thanks Jen for putting the time in the first time, AND updating it! Leggings are my go to! And since I bought the SPANX, my leggin game has been up’ed!!!
Thank you!!!
Omg I love you for this! Thank you! 😍😍😍
My mom uniform just got a major upgrade! 👯♀️
Hi! Quick question, the top you link to, the tunic that you wear in several consecutive photos that comes in several colours, from Nordstrom. It’s dry clean only. Is that really the one you’re wearing? And are you really not washing it at home as a mum of two? I just ordered it bit didn’t read the washing label first and am horrified it’s dry clean only. Wanted to check with you.