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?

Yes.

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

How To Make Leggings Look Intentional: My Casual Outfit Guidelines

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.

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).

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

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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.

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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.

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Chunky Boots To Wear With Leggings

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

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

I just can’t seem to quit them.

xo,
S

Photo credit: Redfield Photography

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