Wearing dresses over skinnies or leggings is an easy combination that some will wear forever. Wearing the frock over flared or straight cropped pants or jeans is a fresher version of the combination, and one I’m into quite a bit. The subtle or fuller flare on the hems of the bottoms adds a more fashionable sensibility to the outfit. To my eye the vibe looks chic, elegant, fun and a little avant-garde. 

Combine a length of dress that falls somewhere between mid-thigh and above the kneecap with a pair of flared or straight cropped jeans or pants. Straighter knee-covering midi dresses can work (here I am wearing this with jeans last year),  but you’ll probably need a heel with that pairing unless you have a very long leg line. Finish off the look with footwear that works with the bottoms, accessories, and add layers for warmth if necessary.

Keep the contrast low, the colours tonal, or create a column of colour between the dress and crops if you’re concerned about chopping up your long lean line. You’ll want a dress that is fluid over the waist so that you can’t see the silhouette of your jeans or pants. Unstructured shirt dresses are ideal for this look. That said, waist-defining dresses made of thicker fabric, or with strategically placed ruching can glide over the waistband of the bottoms quite successfully too. No grinning. 

I don’t have great visual examples, but the Summery renditions of the vibe below and in this pin might get your creative juices flowing. Mess around in your closet and combine a dress with cropped flares or straights, and see what happens. Heels are not essential for the look.

REDVALENTINO Cashmere and Point D'esprit Mini Sweater Dress

I wore my linen and denim shirt dresses over straight white cropped jeans quite a bit last Summer. I finished off the outfit with pearls, flat white sandals, and a gold or white bag. I find the insulating and structured feeling of the jeans under my dress quite comforting. 

Just last week, I pulled together a dressier version of this vibe for a friend’s birthday party at a restaurant. I combined my new black holiday dress with dressy black cropped flares, black Heattech socks, cream booties, and pearls. I finished off the outfit with an orange bag, chartreuse coat, matching patterned scarf, watch, and green specs. I enjoyed how layering the dress over the pants amps down the dressiness of the frock. Here are the exact items of the outfit. I was very comfortable, and felt fab.