What To Wear With Leggings Now: Mid-Calf, Lug Sole Chelsea Boots

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I’ve been wearing black leggings for…uhhh…too many years to count. And while they’re not the most exciting item in my wardrobe, they’re not exactly going anywhere, either. So I’m always on the lookout, especially in winter, for new ways to make this old standby feel a little more modern.

A black leggings spruce up, if you will.

This year, the mid-calf, lug sole Chelsea boot has become a particular favorite of mine, in no small part because of it’s so darn practical (the comfort! the resistance to mud!), and because it seems to work with all the jeans I typically wear in winter (mostly straight-leg & skinny). Even better, these boots winterize my cropped jeans. So yeah — I’m a fan.

But the one thing that has elevated these chunky Chelsea boots into almost everyday status is the fact that they look so darn good with my black leggings.

 fashion girls do -- there's wayyyy too much snow and mud and ice where I live to pull that off. I mean...gimme a few months. But for now, I'm sticking with chunky, mid-calf, Chelsea boots.

jacket (s) | hoodie (s) | leggings | boots

And while I want to be wearing sneakers and socks with my leggings — like all the fashion girls do — there’s wayyyy too much snow and mud and ice where I live to pull that off. I mean…gimme a few months. But for now, I’m sticking with chunky, mid-calf, Chelsea boots.

5 Cute Winter Outfits With Leggings & Lug Sole Chelsea Boots

I’ve been wearing the heck out of my mid-calf Chelsea boots, so much so that I now own two pairs: Ganni’s Mid Chelsea Boot in ‘kalamata’ (an olive green color) and Schutz’s Rubber Leather Chelsea Boot (in black). I’ve also rounded up a few more options (found at the end of this article).

In these photos, the leggings I’m wearing are my favorite black leggings, Vuori’s Daily Leggings (size small), but when the temps dip below 10F, they’re not nearly warm enough. In that case, I wear these exact same outfits with Athleta’s Polar Tech Leggings (size small).

ps. We also made a quick little IG reel of these outfits, if interested. Oh, and if you see us on your #fyp? We officially made our debut on TikTok (follow along @themomeditofficial)!

Leggings & Boots Outfit 1: Sporty Monochromatic With a Hoodie

 If I need to run out of the house, I replace my sweatpants with leggings and voilà! Off I go. I do try to liven things up with that cute pink puffer jacket, though.

hoodie (s) | leggings | boots

Admittedly, this is the outfit I wear the most often. If I need to run out of the house, I replace my sweatpants with leggings and voilà! Off I go. I do try to liven things up with that cute pink puffer jacket, though.


Leggings & Boots Outfit 2: Slightly More Elevated Monochromatic

The 1 thing that has elevated these chunky, lug sole Chelsea boots into almost everyday status is that they look so darn good with black leggings. Enter 5 cute winter outfits...

jacket (s) | sweater | similar sweater | leggings | boots

Swapping out the hoodie for a cropped, cashmere sweater, and the two-tone olive boots for a sleeker black pair results in an outfit that is fundamentally the same, but with a slightly different vibe. (Also, in the past I’ve described this Patagonia puffer as “lightweight” and it IS…but I was completely missing the fact that it is JUST as warm as the other short puffers I own, despite their extra heft. I need to do a complete review on this piece; it’s pretty amazing.)

The 1 thing that has elevated these chunky, lug sole Chelsea boots into almost everyday status is that they look so darn good with black leggings. Enter 5 cute winter outfits...

jacket (s) | sweater | similar sweater | leggings | boots


Leggings & Boots Outfit 3: With a Knotted Graphic Tee & Mid-Length Puffer

The 1 thing that has elevated these chunky, lug sole Chelsea boots into almost everyday status is that they look so darn good with black leggings. Enter 5 cute winter outfits...

parka (s) | similar tee (s) | leggings | boots

It’s funny how this outfit (when you remove the coat and boots) looks and feels exactly like loungewear, yet when you add in all of the pieces, it’s instantly elevated into a real outfit. Such is the power of a good graphic tee (or maybe the coat and boots?). IDK. It works. I add in a long-sleeve tee (or turtleneck) underneath the graphic tee when I need more warmth.

The 1 thing that has elevated these chunky, lug sole Chelsea boots into almost everyday status is that they look so darn good with black leggings. Enter 5 cute winter outfits...

parka (s) | similar tee (s) | leggings | boots


Leggings & Boots Outfit 4: With a Cropped, Cashmere Sweater & Long Wool Coat

Personally, I love a cropped sweater with high-rise leggings. The look feels fresh and fun — but in this outfit, the sweater length really doesn't matter. The coat and boots are the focus.

similar coat at Saks | J.Crew | L.L Bean | sweater (s) | leggings | boots

The key point here is the wool coat. Any sort of long-ish wool coat would work here — something that hits riiiight above the knees or longer. A maxi coat would be an epic, totally on-trend option. Personally, I love a cropped sweater with high-rise leggings. The look feels fresh and fun — but in this outfit, the sweater length really doesn’t matter. The coat and boots are the focus.

Personally, I love a cropped sweater with high-rise leggings. The look feels fresh and fun — but in this outfit, the sweater length really doesn't matter. The coat and boots are the focus.

similar coat at Saks | J.Crew | L.L Bean | sweater (s) | leggings | boots


Leggings & Boots Outfit 5: With Preppy Layers & A Parka

The 1 thing that has elevated these chunky, lug sole Chelsea boots into almost everyday status is that they look so darn good with black leggings. Enter 5 cute winter outfits...

parka (s) | sweater (s) | leggings | boots

Sometimes, an old outfit formula just needs a modern tweak. In this case, oversized, preppy layers (button-downs + stripes) look perfect with the updated chunky boots.

Sometimes, an old outfit formula just needs a modern tweak. In this case, oversized, preppy layers (button-downs + stripes) look perfect with the updated chunky boots.

parka (s) | sweater (s) | leggings | boots


Shop Chunky, Mid-Calf Chelsea Boots To Wear With Leggings

xo,

S

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Shana founded The Mom Edit in 2008. She lives with the love of her life (his name's Mike) and their two crazy boys in downtown Philadelphia. She loves a good styling challenge (her engineering side shows eventually), appreciates kindness, and usually picks scotch over wine, sneakers over stilettos, and shorts known as denim-underwear, always.

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