How To Make Your Cropped Wide-Leg Jeans Feel Fresh


One simple word for styling your cropped wide-leg jeans for this year…knee boots. Ok, I guess that’s two words, but trust me when I say not only are they warmer for the cold temps but they solve the issue of which boots work with cropped jeans.

Knee boots are your winter-time friend. They’re my go-to year-round for making dresses feel slightly edgier (like I prefer) and in winter they make wider-leg jeans work!

how to wear cropped wide-leg jeans

Coat (S) | Similar Sweater | Jeans (29) (or these) | Boots

You probably have a pair of these jeans in your closet. But in case you need an update or got rid of them or changed sizes like me, here are some cute jean options for this combo.

My exact pair, The Pilcro Kit Cropped, is amazingly comfy and I bet more of the extended sizes will be restocked soon (some of the Standard have just been!) The famously loved Colette jeans from anthropologie below are probably my other top pick (and they come in Standard, Petite, Tall + Plus sizes, too) but the Wit & Wisdom below have got to be good knowing their rep around here and their price point is great. They also have a cool front seam detail I love.

5 Outfits To Update Your Cropped Wide-Leg Jeans

No matter which pair of cropped wide-leg jeans or pants you have or add to your closet, this combo can work. I do like pairing this darker wash with my darker knee boots for winter and for a dressier overall feel, but you can achieve a successful outfit with lighter wash jeans and lighter boots, too.

Another option is to keep the tops + coats + everything but the boots in a similar lighter value if you have darker knee boots. Bring in a darker bag to tie it together. Since I have the dark-wash denim here I stuck with my two pairs of brown knee boots I wear most often. Black jeans and black knee boots would be gorgeous, too!

1 | Cropped Wide-Leg Jeans: With A Cashmere Sweater + Statement Bag

This is an outfit I can and will wear on repeat. I love that it looks really pulled together but in fact is super comfy. The pop of white my vintage Chloe bag adds is one of my favorite styling tricks, too.

wide leg cropped jeans outfit

Outfit: Sweater (M) | Jeans (29) (or these) | Boots

Accessories: Similar Bag

I highly recommend these Blondo waterproof suede knee boots. They’re not only great in weather, cute and warm, but they also have a cushioned insole and they’re not tight in the calves. And this Quince Mongolian Cashmere sweater is a real winter go-to for me. It holds up so well and is just over $100. It would make a great gift.

2 | Cropped Wide-Leg Jeans: With A Blazer + Scarf

This next look would be a great airport outfit actually, if your jeans are comfy. Wearing a scarf as a wrap is my fav for travel and packing blazers in a suitcase is never my favorite. So this outfit gives the option of wearing your harder-to-pack items (like those knee boots) and looks chic but is surprisingly comfy.

wide leg cropped jeans outfit

Outfit: Similar Blazer (Plus Size) | Tee (M) | Jeans (29) (or these) | Boots

Accessories: Similar Bag | Scarf

The tee underneath is perfect if it gets too toasty. Choose a statement bag big enough to be your tote for the plane and voila. I think I’ll be rocking this later this month exactly!

…or grab a GIANT scarf! If it’s even colder and you want a fun statement piece? Grab a Lenny Kravitz style giant scarf and it’s honestly like a wearable blanket. Haha. I freaking love this combo for the right days. This would be perf for really cool mornings and sunny warmer-ish afternoons like we get here this time of year.

wide leg cropped jeans outfit

Outfit: Similar Blazer (Plus Size) | Tee (M) | Jeans (29) (or these) | Boots

Accessories: Similar Bag | Scarf

3 | Cropped Wide-Leg Jeans: With A Plaid Coat + Cabled Sweater

This coat, friends. I cannot express how comfy and lovely it is. The plaid color combo is perfection and the coat itself is super soft. I love the long coat + cropped jeans combination for some juxtaposition. And who doesn’t love a great cable knit classic sweater. The one I’ve linked to here is even better IMO. (Mine is the sold out Madewell one but the sleeves were too short, so it went back.)

wide leg cropped jeans outfit

Coat (S) | Similar Sweater | Jeans (29) (or these) | Boots

This is another wear-on-repeat look I’ll be rocking all winter. Any maxi coat you have would be great in a similar combo. And here I’ve pulled out my brown croc Schutz knee boots that take the look up a notch. While not quite as cushiony as the Blondo boots, these have taken me through 4+ years now and I love pairing them with dresses for events. They’re comfy enough for this hardly-ever-wears-heels gal to wear for a few hours and be just fine.

4 | Cropped Wide-Leg Jeans: With A Faux Leather Puffer + Structured Bag

I love this fun combo, but I think I’d love it even more if I had grabbed a white or ivory tee, aka match the tee to whatever cropped puffer you have. I love the proportions of the puffer with the wide-leg crops and the fact that it’s faux leather kicks it up a notch.

wide leg cropped jeans outfit

Outfit: Puffer (M) | Tee | Jeans (29) (or these) | Boots

Accessories: Bag | Similar Earrings

The structured bag adds another chic element making this lean more dressy than sporty. It’s a fun wearable combo. Swap in a cropped sweater if you need more warmth.

5 | Cropped Wide-Leg Jeans: With A Metallic Top For A Casual Holiday Party

Here I switched to my fancy knee boots again…the ones that make me feel like a million bucks. Shiny pieces are always a good call for a party and honestly any shimmery, glittery party top would be great here.

Outfit: Top (M) | Jeans (29) (or these) | Boots

Accessories: Similar Clutch | Similar Earrings

This party top from Anthro is cute, but I wasn’t blown away by the fit. I think I’d go with a metallic cami or this sequined Free People top instead, but the idea is the same…glitzy + jeans + fancy knee boots + jewelry.

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Hope this is helpful in your quest to make those cropped wide leg jeans that work well in summer wearable in the colder months. As always, let us know if you have a comfy pair you love in the comments.



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