Style, Winter

When to Wear Leggings

Let me be clear with you: I don’t think leggings are pants.  However, I do believe that there are perfectly acceptable opportunities to wear leggings, and that they should be worn often. Denim Shirtdress, Green Leggings, Black Booties, and Yellow Cardigan Denim Shirtdress, Green Leggings, Black Booties, and Yellow Cardigan Denim Shirtdress, Green Leggings, Black Booties, and Yellow Cardigan Denim Shirtdress, Green Leggings, Black Booties, and Yellow Cardigan Denim Shirtdress, Green Leggings, Black Booties, and Yellow Cardigan Denim Shirtdress, Green Leggings, Black Booties, and Yellow Cardigan

[In these pictures, I’ve got two books in my hand. These books are super special to me, so much so that I gave them their own post. Check it out here!]

While all elements of the outfit [with the exception of the shoes] are older, they are all also pieces that are common to find. My shirtdress is from the Levi’s Outlet, but Forever 21 has many options that I’m a fan of. This one is rather short, which makes it much better suited with leggings than it is on it’s own. The leggings are fleece lined [because it’s literally freezing outside] from Jane, but Forever 21 also has a pair in this same dark green color.

I feel like leggings really started becoming popular during my later years in college. I’ve got to be honest, I used to strongly judge any girls that I saw wearing them as their only source of bottoms. That was before I owned a few pairs and truly realized the extent of their comfort. Even though I’m a legging convert myself, I still cringe a bit when I see the complete view of a pair of leggings on a girl. Some things are not meant to be seen.

So when should you wear leggings?

One. With a dress. Or a skirt. That’s a pretty self-explanatory one. They are like thicker, warmer tights. Hello extending the life of your summer dress wardrobe.

Two. Around the house. If they are the comfort level of pajamas, then wear them as pajamas. ‘Nough said.

Three. With a tunic or shirt that is long enough to cover up your rear end. This is what leggings are basically made for. They are perfect for those pieces that are supposed to be a dress but really are more like tunics and make you feel incredibly uncomfortable to wear all by their lonesome.

Four. With big sweaters. Please place an emphasis on big. This is my personal favorite way to wear leggings. Talk about the ultimate comfort. Throw on boots or booties and I bet you are looking super cute.

Five. To work out. Ok, so these might need to be more of the yoga-pant variety, and definitely not see through, but they are the perfect stretchiness for getting your fitness on.

When shouldn’t you wear leggings?

One. With an itty bitty tank top. I’m sorry my dear, your behind is on display.

Two. With hi-lo tops. Truth be told, these types of shirts aren’t my favorite with any bottoms. I truly believe that when you wear leggings, there should be no chance that underwear can be seen from any perspective.

Three. Basically, with any short top.  No explanation. Duh.

Four. To a job interview. Let’s kick up the class level for this life event.

Five. When you first meet the boyfriends ‘rents. You really, really don’t want to come across as a floozy the first time you meet them. Save this for the days spent together later on.

*Warning: Do not confuse leggings with jeggings. They are a separate entity, and certainly acceptable in more situations:).

Shop the look:

Linked up with: Still Being Molly // Whitney a la Mode // A Little Bit of Cheer // A Lovely Little Wardrobe // Fizz and Frosting // Sincerely Jenna Marie // More Pieces of Me // Pink Sole // Michelle’s Pa(i)ge//Northwest Blonde //  Sandy a la Mode // Cute & Little // I Do deClaire  // Garay Treasures // Style Elixir // Two Peas in a Blog // Elegantly Dressed and Stylish // The Fashion Canvas // Walking in Memphis in High Heels

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  • ADA

    I love leggings. Your hunter green pair is lovely – I own some similar one in a dark green. Love that cozy mustard cardigan especially with that color combo of a dark color, a soft light neutral and a bright color. The blouse is feminine and fun. Love that first photo of you with the books. Perfect for the teacher you are. Happy Monday!

  • Haha. This cracks me up! I completely agree with your assessment of leggings!

  • Perfectly acceptable and should be worn often. Leggings ideas = perfection!

  • LOL, I loved your don’ts list. A job interview…yikes! I love how you styled your leggings and I agree completely that they can totally work if you wear them right.

  • Darcy

    That sweater is soooo cozy!!

  • I love the leggings! That mustard cardigan is gorgeous too!

    Abby of Life in the Fash Lane

  • Penny @ pennyspassion.blogspot

    You look adorable in that outfit! I totally agree with your list of when/not when too.

  • Katey Haines

    Great post. I agree with all the above. There is no need to see certain things. I love the comfort of leggings, but I don’t wear them much. Not really sure why!


  • Very cute look! Loving the pleats on your denim shirt dress and the booties complete your look perfectly. Great tips on when and when not to wear leggings. Totally agree on fleece-lined… Love them!

  • Totally totally totally agree with these tips for wearing leggings! They are comfortable but there are definitely ways to wear them!

  • Love that this is WHEN and not HOW! I think some people forget that they aren’t always the best choice!
    Thanks for linking up with us on Start the Week Stylish!
    – Ana Luiza
    The Northwest Blonde