Sorry to break it to you, but we’ve officially entered the autumn season (*sobs*).
It’s time to think about how to update our wardrobes for the weather ahead, and upgrade our summer faves for the chillier months.
It helps to lean on versatile clothing options, such as cropped jeans: trousers which can be dressed up or down, and which can easily be layered for more warmth. However, while cropped jeans are a transseasonal styling hero, some folks struggle to choose the footwear with which to pair with this well-worn fave.
Everyone’s clicking on…
Thankfully, team Cosmo has been doing some digging. After consulting plenty of street style pics, scanning social media for inspo, and doing some of our own IRL trial-and-error with the footwear in our wardrobes, we have compiled a definitive guide of the best shoes to wear with cropped denim.
So, without further ado, check out our picks — complete with helpful styling tips — below!
Cropped jeans and sandals
Let’s start off with the most optimistic of the pairings: cropped jeans and sandals. Naturally, this is one for the warmer days this autumn, but if you’ve invested in new sandals or hopped on the luxe flipflop trend, get some more mileage out of your footwear by pairing yours with cropped jeans.
Black or white leather sandal styles work best here, as this in-keeps with the more polished turn fashion is taking for the new season. Due to the more relaxed vibe of sandals, you’ll want to make this one more seasonally appropriate by opting for structured denim — whether dark, raw denim or a more formal, cropped cigarette jean. On top, try a crisp white, black or grey tee, a shirt, or a fine gauge jumper.
Cropped jeans and loafers
Loafers are about to be everywhere, so it makes sense to hop on the trend early so you can get the most mileage out of this preppy staple. These particularly versatile shoes can be worn with cropped skinnies, as well as cropped wide-leg styles (though may be trickier to style with flares).
Loafers work particularly well as workwear, and can be styled with a darker wash pair of jeans for this purpose. Notoriously difficult to wear in, due to the stiff leather, be sure to wear yours with socks — but be intentional with either a preppy patterned pair or a sheer pair of hold-ups.
Cropped jeans and kitten heels
Kitten heels are the perfect shoe to elevate a cropped pair of jeans into more formal attire, whether for a date, or an event. Generally, dark-wash or black rinses work best with this style of shoe, and a pointed toe will make the look more glamorous still.
It’s worth mentioning, though, that peep-toe shoes worn with tights or socks are set to be the next big heels trend (don’t say we didn’t worn you). On top, you might want to consider a slinky camisole or even going for the dress-over-jeans look by wearing a silky slip dress.
Cropped jeans and ankle boots
Nothing feels more autumnal than a good pair of boots, which makes them the perfect companion for your cropped jeans. This season, boots are getting slouchier and will find harmony with lighter-rinse, flared or wide-legged jeans as part of the broader boho revival.
On the whole, this is more of casual style and can be worn with floaty tops or even a statement slogan tee to really tap into the late aughts mood influencing fashion atm. However, you can go for a dressier version of this look by opting for a darker, sleeker and more structured heeled boot and and a pair of dark, straight leg jeans.
Cropped jeans and trainers
Cropped jeans and trainers are a dreamy match — perfect for busy days running errands, grabbing coffee with a friend, or heading into a more casual office environment.
Lowtop (such as the Adidas Superstar) and low profile (ie the Puma Speedboat) trainers go well with skinnier styles whereas hightop shoes (like your good ol’ Converse Chuck Taylors) look great with a pair of flared, cropped jeans.
This is generally quite a lowkey look, and can be worn with a simple — or statement — tee, or a shirt. A tracksuit jacket or lightweight denim jacket can be a good addition as an easy layer which gives the look a sporty edge.
Megan Wallace (they/them) is Cosmopolitan UK’s Former Sex and Relationships Editor covering sexual pleasure, sex toys, LGBTQIA+ identity, dating and romance. They have covered sexuality and relationships for over five years and are the founder of the PULP zine, which publishes essays on culture and sex. In their spare time, they can be found exploring the London kink scene and planning dates on Feeld.
