40 Ways to Style Leggings!

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!

Leggings Outfit

Tunic  //  Denim Jacket (Similar HERE)  //  Leggings   //  Wedge sneakers (go up half a size)

Leggings Outfit

Jen:  Leggings // Top  //  Denim Jacket  //  Shoes  |  Remi:  Jacket //  Shoes  //  Tunic

Leggings Outfit

Leggings (similar HERE) //  Top (size up one)  //  Sneakers //  Jacket

Leggings outfit

Leggings  //  Flats  //  Sweater

Leggings Outfit

Leggings  //  Gladiator Booties  //  Top (size small)  //  Chambray Top

Sweater (sold out, similar HERE)  // Leggings  // Boots

Sweater //  Leggings  // Shoes

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

Leggings Outfit

 

Camo Sweater //  Mustard Top  //Leggings

Leggings Outfit

Leggings  //   My Hunter Boots / Remi’s Hunter Boots  //  My Sweater / Remi’s Sweater

Leggings Outfit

Leggings Outfit

Black Top  //  Similar Vest //  Leggings //  $20 Rose Gold Sneakers

Leggings Outfit

Sweater //  Leggings //  Wedge Sneakers (size UP half a size)

Leggings Outfit

Amazon Tunic //  Boots (size down!)  //  Scarf  //  Leggings  //  Sunglasses 

Leggings Outfit

Sweater (wearing xs)  //  Leggings  //  Boots  // Remi’s Dress //  Remi’s Boots 

Leggings outfit

My Leggings / Remi’s Leggings  //  My Boots / Remi’s Boots  //  My Jackets / Remi’s Jacket

Leggings Outfit

Leggings //  My Boots / Remi’s Boot //  My Sweater  / Remi’s Sweater 

leggings outfit

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

legging outfits

Same tunic as above  //  Similar Boots  //  Vest  //  Bag // Leggings 

Same tunic as above  //  Leggings  //  Pumps  //  Trench Coat

legging outfit

Leggings  //  Booties  //  White Tee (size small)  //  Mustard Sweater (xs)

legging outfit

Leggings //  White Tee (size small)  //  Ugg Boots  //  Similar Cardigan  //  Bag

legging outfit

White Tee //  Leggings (sold out)  //  Similar Plaid Top  //  Adidas

legging outfit

Moto Jacket  //  Leggings  //  Tank  //  Wedge Sneakers (go up half a size)

legging outfit

Moto Jacket  //  Leggings  //  Tee  //  Adidas

legging outfit

Tank  //  Cardigan (50% OFF today only)  //  Leggings  //  Flats

legging outfit

Striped Tee (size up one)  //  Leggings  //   Jacket

legging outfit

Same top as above  //  Similar Jacket  //  Leggings  //   Wedges Sneakers  (go up half a size)

leggings outfit

Same top as above  //  Vest   //  Leggings  // Wedge Sneakers

legging outfit

  Tunic Top  (if between sizes, go down)  //  Booties  // Bag //  Leggings

legging outfit

Jacket (xs, other colors available)  //  Leggings  //  Booties  //  White Tee (size small)

leggings outfit

Sweater (size xs) //  Leggings // Boots (Similar option HERE)

Leggings  //  Tank  //  Green Top  //  Adidas

legging outfit

Nikes  //  Sweater  //  White Tee  // Bralette  //   Leggings

legging outfit

Cardigan (xs)  //  White Tank  //  Leggings  //   Booties

legging outfit

Tunic (size small)  //  Wedge Sneakers (go up half a size)  //  Leggings  //   Green Jacket

Leggings  //   Tunic  //  Scarf  //  Adidas

legging outfit

Striped Tee //  Sweater  //  Ugg Boots  //   Bag  //  Leggings

legging outfit

Hunter Boots //  Leggings  //  Vest  //   Similar Tee

legging outfit

Sweater   //   White Tee  //  Adidas

Cardigan  //  Tank  //  Flats  //  Bag  //  Earrings  //  Leggings

legging outfit

Sweater  //  Leggings  //   Wedge Sneakers (go up half a size)

legging outfit

Striped Tee  //   Similar Sweater   //   Leggings   //  Ugg Boots

legging outfit

Leggings  //   Flats  //   Mustard Top (size small)  //  Chambray Top

legging outfit

Sweater (sold out)  //  Boots (SO COMFY)

leggings outfit

Cardigan (I LOVE this)  //   Slippers   //   Leggings  //   Tank

legging outfit

Sweater  (wearing xs)  //  Boots  //  Similar Boots  //  Leggings

Sweater (xs) //   Leggings  //  Adidas

legging outfit

Chambray Top (this one is a little too short for leggings)  //  Vest  //  Leggings  //   Flats

legging outfit

Tunic (xs)  //  Leggings  //  Miller Sandals (color: sand)

legging outfit

Same tunic as a above //  Vest  //  Boots  //  Similar Boots

legging outfit

Same tunic as a above  //  Tank  //  Wedge Sneakers (go up half a size)  //  Leggings

legging outfit

Tank //  Cardigan  //  Leggings  //   Flats

legging outfit

Sweater  //  Leggings  //   Wedge Sneakers  (go up half a size)

legging outfit

I LOVE this sweater!!  //  Tall Boots (similar boots) //  Leopard Booties

Sweater //  White Tee  //  Leggings  //   Adidas

legging outfit

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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Hi, I'm Jen!

I'm a mom of two who loves on coffee (and wine) and a lot of humor! If you enjoy affordable + achievable style, then you're in the right place. I'm so glad you're here!

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55 Comments

  1. Maridel Dubb wrote:

    Wowza! Thanks for doing this. I’ll be sure to reference back to this post everytime I need a leggings outfit! You’re awesome 😁

    Posted 10.7.18 Reply
    • I’m SO glad this post is helpful! Thank you!!!!

      Posted 10.7.18 Reply
      • Stacey wrote:

        Could u tell us who the make is for the checkered purse?

        Posted 2.28.19 Reply
    • Natalie wrote:

      Amen!! Jennifer is the BEST!

      Posted 10.7.18 Reply
    • Channing wrote:

      For up to date 2019 leggings and best deals please go to

      only-options.myshopify.com

      Posted 1.20.19 Reply
  2. This is EXACTLY what I’ve been needing!! I tried to search ideas on Pinterest yesterday but didn’t have much luck. Thank you!!

    Posted 10.7.18 Reply
    • YAY!!! I’m so happy that it’s helpful!!

      Posted 10.7.18 Reply
      • April wrote:

        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

        Posted 1.2.19 Reply
  3. Thank you for doing this! I loved looking at all the different styles!

    Posted 10.7.18 Reply
  4. Jill wrote:

    Thank you so much! This is so helpful!

    Posted 10.7.18 Reply
  5. Bonny wrote:

    This is so perfect! Thank you so much! I am beyond excited to start styling 🙂

    Posted 10.7.18 Reply
  6. Josiline wrote:

    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.

    Posted 10.7.18 Reply
    • Josiline wrote:

      I meant styling not staying 🤦🏼‍♀️

      Posted 10.7.18 Reply
      • I definitely plan to do similar posts in the future! 🙂

        Posted 10.8.18 Reply
  7. Karen W Bank wrote:

    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!

    Posted 10.8.18 Reply
    • 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! 🙂

      Posted 10.8.18 Reply
  8. Lisa wrote:

    This is great! You’re the best.

    Posted 10.8.18 Reply
  9. Kelli wrote:

    Exactly what I needed and was hoping for!!!

    Posted 10.8.18 Reply
  10. Rachel wrote:

    LOVE this post and all the links for the pieces!!!

    Posted 10.8.18 Reply
  11. Maggie wrote:

    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

    Posted 10.8.18 Reply
  12. Allexa Parham wrote:

    You just made all my Wardrobe dreams come true with this post!! Thank you taking the time to do this ❤️❤️❤️

    Posted 10.8.18 Reply
  13. Niki wrote:

    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!

    Posted 10.8.18 Reply
  14. Wow!! Awesome post- I got so many great ideas for fall! I love every single way you styled your leggings!

    Posted 10.8.18 Reply
  15. Athena Altomerianos wrote:

    I wish I could save this whole post!! All your outfits are great!! You are adorable & real & I soooo enjoy your blog!! ❤️

    Posted 10.8.18 Reply
  16. Kristina wrote:

    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!!!

    Posted 10.8.18 Reply
    • Corinne wrote:

      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

      Posted 10.8.18 Reply
  17. Cory wrote:

    Holy crap! This post is thorough! You gave me so many ideas (and also just made me order about 5 new sweaters!)

    Posted 10.8.18 Reply
  18. Allison wrote:

    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

    Posted 10.8.18 Reply
  19. Maegan wrote:

    This post is amazing!! Thank you!
    How do the spanx leggings fit? True to size?

    Posted 10.8.18 Reply
  20. Kimberly wrote:

    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!!!

    Posted 10.9.18 Reply
  21. Stephanie wrote:

    SO perfect for my last month of pregnancy! Thanks!

    Posted 10.11.18 Reply
  22. Christy wrote:

    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.

    Posted 10.12.18 Reply
  23. Lessie wrote:

    Love them all! Thank you!

    Posted 10.13.18 Reply
  24. Sophia wrote:

    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

    Posted 10.15.18 Reply
  25. Joni wrote:

    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!!! 😗

    Posted 10.15.18 Reply
  26. Alexandra Rodriguez wrote:

    Umm ok all my outfits are going to be created based on this post…thank you so much!

    Posted 10.15.18 Reply
  27. Kelsey Ledford wrote:

    This post 🙏🙌 is EVERYTHING!! Thank you!!

    Posted 10.15.18 Reply
  28. Morgan Dennard wrote:

    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💜

    Posted 10.23.18 Reply
  29. Anna Lamarre wrote:

    I love this post! I’ve referenced it at least 4 times already!! Your a life saver!!

    Posted 11.3.18 Reply
  30. Tricia Hernandez wrote:

    Are the uggs the sort or tall style?

    Posted 11.7.18 Reply
  31. Liz Lawson wrote:

    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!

    Posted 11.21.18 Reply
  32. Elizabeth wrote:

    Would anyone make recommendations on length? I’m 5’7” & not sure whether to order regular or tall leggings. Mostly wear booties. Great post!

    Posted 11.25.18 Reply
  33. 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!!!

    Posted 12.5.18 Reply
  34. Tiffany wrote:

    Omg I love you for this! Thank you! 😍😍😍
    My mom uniform just got a major upgrade! 👯‍♀️

    Posted 12.6.18 Reply
  35. Sarah wrote:

    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.

    Posted 2.28.19 Reply
  36. Nice!! I could use some of these styles! Thanks for letting this out. :))

    Posted 8.29.19 Reply
  37. Valerie wrote:

    Thanks for this! I really have been wanting to have an outfit with leggings, it’s out of my comfort zone but just what I’m looking for. I now have something to go by when shopping since I’m not good at putting outfits together.

    Posted 9.23.19 Reply

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