The flare on cropped jeans can be subtle or dramatic. A pair of cropped straight leg jeans creates a more subtle flare at the hem, which is usually an easier outfit proportion to work with. That said, if you have wider calves, a wider flare will be more comfortable. 

Flared crops look best to my eye when the hem finishes two to four inches above the ankle bone. That way the length looks intentionally cropped and not like you’e wearing bottoms that are too short. Lengths that are as long as half an inch above the ankle bone can work, but you’ll need to put more thought into the proportions of the rest of the outfit. It’s easier to create a longer leg line with a slightly shorter length, and an inch can make all the difference. (Note the shorter length of the flared crops on the models in the photos below.) 

You’ll see flared crops styled with all sorts of trendy shoes, but to my eye some styles look better than others. Here are six styles of shoes that create outfit proportions with flared crops jeans that are just flattering enough. You can apply the guidelines to trousers too.

1. Heeled Ankle Straps

This is a flop proof way to create a longer leg line with flared crops because the ankle strap closes the gap and creates a continuous line up the leg. The strap must be positioned on or above the ankle bone. The model showcases sky scraping platforms, but any heel height is good in a dressy or casual style of shoe. You’ll find the right ankle strap on heeled footwear styles like pumps, sandals, sandal booties, cage heels and cut-out booties.

Heeled Ankle Straps

2. Flat Ankle Straps

Trendy lace-up styles create “the ankle strap effect”, thereby closing the gap with the laces that are positioned well above the ankle bone. You’ll also find the right ankle strap on flat footwear styles like sandals, pointy toe flats, sandal booties and cut-out booties.

Flat Ankle Strap

3. Booties

You can wear flared crops in Autumn and Winter with booties. The booties on the model here are high in the shaft, which creates a longer leg line (especially when the booties are a low-contrast colour to the jeans). But feel free to wear booties or shooties with lower shafts as long as the openings fit close to the ankle. 

I don’t like socks to peek through when I sit down and cross my legs, and prefer the look of “bare skin”. I use nude knee-highs to create a bare-leg effect because that looks more dressy and polished than socks with my own outfits. Others might not find knee-highs sufficiently comfortable or insulating.


4. Oxfords

The next three styles of footwear are less elongating than the first three because they don’t cover part of the ankle. That breaks up the continuous vertical line from foot to hip. But the high vamps of these styles add back a bit of that “continuous line”, which you can see with the oxfords below. Furthermore, the silver oxfords create a low contrast against the skin tone of the model and her faded jeans, which strengthens the flow of the vertical line. You would break the flow of the line in this outfit if the oxfords were a high-contrast black.


5. Sneakers 

Sneakers are sporty oxfords and a very similar style of shoe (high-vamped flat lace-up), so the same guidelines apply. The white sneakers here do create a higher contrast against the model’s darker skin tone, but the shorter length of the crops, the high vamp of the shoe, and the semi-tuck of the top offsets the more horizontally cutting effect.


6. Loafers 

Loafers are slip-on versions of oxfords and laced sneakers, and just as high in the vamp. Here the model is wearing silver loafers that are low contrast to her skin tone, but high contrast to the dark wash of the jeans. The low contrast footwear lengthens the line of the leg from the hem of the jeans down to the toe box of the shoes. The shorter length of the jeans lengthens the leg line from the calves down, while the semi-tuck of the top lengthens the line from the hips upward.


Of course, the concept of creating outfits that are “just flattering enough” is on a sliding scale, and you’ll need to take into account your figure flattering priorities and go with what makes you feel fab. Some like to wear low-vamped pumps and flats with flared crops, and while that isn’t my own preference, the combination can work if the hems are sufficiently short. Pointy toe boxes also help elongate the leg. 

You can further elongate the leg line from the hips upwards by fully or semi-tucking the top. You’ll find that the level of the contrast of the footwear against your skin tone and/or the colour of the crops will also make a visual difference.

My own eye is very, very particular about a cropped pants length and footwear pairing, and I can’t help but have my poison eye moments with some combinations. Yet flared cropped jeans are a wardrobe essential at the moment and I have several pairs that are in frequent rotation. I prefer to wear heeled and flat ankle strap footwear with my flared crops, but have also worn laceless flat oxfords and loafers. I don’t like the Tomboy pairing quite as much, but it’s VERY comfortable so I make sure I’m sporting a girly support act with those footwear choices. I also wear a cropped top or semi-tuck my top so that I lengthen the leg upward from the hips.