My New Rules For Leggings-As-Pants


Most days, I find that I’m still reaching for my leggings. Partly because, yes, I am running off to work out but also because of a combination of cold weather, being busy and — like Laura — hating all my jeans right now.

When I’m heading to an actual workout class, it’s easy to make my leggings feel fresh: I add a cropped fleece, socks, running shoes and done. It’s easy.

But when I want to make leggings look like an actual outfit…what’s the trick for 2022 (soon to be 2023)? Are there rules?


(Actually, no — never rules. But I do have…thoughts.)

How To Make Leggings Look Intentional: My Casual Outfit Guidelines

The best way to dress up leggings? W/ a casual, sporty outfit like this 1 with a cropped workout top, a sherpa jacket & chunky lug-sole boots.

jacket (S petite) | top (M) | leggings (S) | boots | similar bag | similar necklace | earrings

OK, so here are my personal “rules” for how to wear leggings right now. I hate rules, so take everything here with a huge grain of salt and wear whatever the hell you want. That said:

  • Outerwear: Short and boxy. While “cropped” is a bit aggressive, a shorter, boxier jacket (or sweatshirt), like this sherpa one from Athleta, is my top pick with leggings right now. And while I’m thrilled with the black-and-white combo I’m wearing here, a monochromatic moment can also make leggings feel really fresh and modern.
  • Tops: Anything that fits under the short, boxy outerwear. This can mean anything from a cropped workout top to a long button-down that intentionally hangs below the outerwear…but in a cool way.
  • Boots: Flat, chunky lug-sole boots are the perfect shoes to wear with leggings. Short or tall — doesn’t matter as long as they’re flat and chunky.
  • Overall vibe: Casual and somewhat sporty. While I’m not opposed to pops of luxe texture (the sherpa collar, for example) or jewelry (I’m wearing both earrings AND a necklace here), each piece still has a sporty or casual feel. Even my leather bag — an old Clare V. — is a duffle shape, which has an inherent sportiness built in. This makes the leggings feel intentional, like they’re meant to be part of this outfit instead of an afterthought.
Pairing leggings with slightly elevated casual pieces makes them feel intentional instead of an afterthought.

jacket (S petite) | top (M) | leggings (S) | boots | similar bag | similar necklace | earrings

Side Note: This “jacket” I’m wearing is actually Athleta’s sherpa-lined sweatshirt (yes, you read that right — a SWEATSHIRT), and it’s freaking amazing. I cannot recommend it enough! The size range (petite, regular, tall and plus sizes) is glorious, ensuring the best possible fit, and it’s also available in black or brown. Best of all? ON SALE. Go now — I’ll wait. (I’m wearing a size small petite, for reference. I’m just under 5’3″, 120 pounds).

This "jacket" I'm wearing is actually Athleta's sherpa-lined sweatshirt (yes, you read that right — a SWEATSHIRT), & it's freaking amazing.
The size range of Athleta's sherpa jacket is glorious, ensuring the best possible fit (petite, regular, tall & plus sizes), & it's also available in black or brown.
While I'm thrilled with the black-&-white combo I'm wearing here, a monochromatic moment can also make leggings feel really fresh & modern.
Wear leggings with anything from a workout top to a long button-down that intentionally hangs below the cropped outerwear...but in a cool way.

jacket (S petite) | top (M) | leggings (S) | boots | similar bag | similar necklace | earrings

Jackets To Wear With Leggings

If you’re interested, here are a few other jackets I recommend wearing with leggings. Many of these I own, others are just similar.

Sweaters & Sweatshirts To Wear With Leggings

Here’s a short list of the sweatshirts and sweaters I’ve been pulling on with my leggings, as well as a few similar pieces that caught my eye.

Chunky Boots To Wear With Leggings

The key? Flat, chunky lug-sole boots. These have the added upside of being decidedly practical too.

How are you guys wearing leggings these days (if at all)?

I just can’t seem to quit them.


Photo credit: Redfield Photography

Hey, Pinners…

Never know what to wear with leggings? Here are some "rules" on how to dress them up in a casual yet intentional way (think: lug-sole boots & cute tops).
How often do you want to hear from us?


  1. I am a huge jeans girl but have been hating the waistband lately too! Happy to know I’m not the only one (at nearly 49 myself). So yes, still team legging when WFH.

  2. Can we talk about your hair?!! LOVING the color and the wavy/curly look. How you got your dark brown hair that shade of blonde (without the brass) is a scientific marvel. LOVE it!

    • Haha – thanks! This was a pandemic silver lining. Since I didn’t get my hair done for over a year, it actually grew in…lighter than we thought. So Shannon (my stylist) was all oh heyyyyy let’s lean in and here we are.
      The waves are from this thing:

  3. I am with you and Laura, just not into my jeans right now. This is helpful. And I know you said no rules, wondering about this look but with a long duster/wool coat. For some reason I have a hard time wearing shorter items with leggings. (Maybe from all the years I told myself leggings weren’t pants?) Do you think a similar vibe could be had with one of those coats?

    • Oooo…a duster with leggings is PERFECT. I think the look (if you’re looking to modernize a bit) is one of two extremes: really short or really long. A long duster + sneaks would be a very model off duty vibe. Love this idea.

  4. Shana, appreciate the insights; going to try it this weekend once off Covid quarantine. Need to try it with boots as it is cold and wet here. Thanks for the inspo!

  5. I just received my jacket today based on your recommendation. It’s really cute and cozy. I can’t wait to try to recreate your look with leggings. I wonder if anyone has washed/dryed it yet and how it looks after? Thanks for everything you do, TME is a fave!

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