Skip to Content

What Shoes to Wear with Jean Shorts-Ladies, The Best Choices

What Shoes to Wear with Jean Shorts-Ladies, The Best Choices

The beauty of jean shorts is that they go with anything and with any shoes.


You can wear them in all seasons, changing your shoes for different looks and different weather.

So let’s find the answer to the question: What shoes to wear with jean shorts?

What Shoes to Wear with Jean Shorts

Jean shorts are versatile, so they can be worn with a range of shoes. Sneakers or trainers are a popular option for any season, while flip-flops or flat sandals are great for Summer. They can also be worn with gum boots or mules in Fall and sheepskin boots in Winter. Strappy sandals or closed wedge espadrilles can give jean shorts a slightly more glamorous look.


What Shoes to Wear with Jean Shorts

Boots and shorts? Big YES

After wearing trousers, leggings, and tights in Winter, it’s time to break out your jean shorts in Spring.

And to set your feet free. As the weather warms up, it may be best to stick to wearing sneakers or ankle boots.

Why not go halfway and wear a pair of ankle-length rubber gumboots?

They will keep your feet dry and mostly warm.

I also find moccasins great as in-between shoes to wear with jean shorts.

As the weather warms up, take the plunge and wear mules or pumps with your jean shorts.

If I want to add a bit of glamour, I go for a pair of block heels or wedges.

Spring is also the time when the world bursts into color, so don’t hold back when you choose the shoes to wear with your jean shorts.

Pair them with bright yellow slip-on sandals, or chunky orange platforms.

You can also make a statement with bright purple platform sneakers.


What Shoes to Wear with Jean Shorts

Sneakers are always a good option

Summer just has to be the perfect season to wear jean shorts.

They can be worn with flip-flops or flat, slip-on sandals on really hot days, especially along the beachfront.

On the other hand, you can put on a pair of bum shorts and wear high strappy sandals for a showstopper outfit.

One of the classic looks is to wear mom jean shorts with platform sandals and you will rock the retro look.

These high-waist shorts can also look great with low-cut sneakers.

Knee-length, Bermuda jean shorts can be paired with slip-on mules or low-cut slip-on canvas sneakers.

You can also wear them with thong sandals.

Mid-thigh jean shorts are the perfect garment for hiking, so you can wear them with hiking boots.

Make sure you wear thick hiking socks too.

If hiking is not your scene, but you want to get out and about, trainers are the way to go.

What Shoes to Wear with Jean Shorts

Hiking boots and shorts are the perfect fit


What Shoes to Wear with Jean Shorts

Jean shorts are very versatile

Fall is the in-between season, so you can take liberties with the shoes you wear with your jean shorts.

On warmer days, reach for a pair of sneakers. On cooler days, either trainers or some boots will be perfect.

Jean shorts are great for yard work, like raking the leaves.

Make sure you wear a substantial pair of hiking sandals or old trainers with shorts.

If you are mowing the lawn, then you must at least wear an old pair of trainers. Make sure your whole foot is covered.

When you go out and about in Fall and wear shorts, you can add a pair of leggings underneath them.

Complete the outfit by wearing rubber boots if it is raining, or slip-on mules on dry days.


What Shoes to Wear with Jean Shorts

Shorts can also be worn in winter

Don’t think that jean shorts are only suited to be worn in Summer.

Just because they leave your legs exposed, it doesn’t mean you have to pack them away when the weather gets cold.

This means you can wear them with your best winter shoes.

On warmer winter days, I like to wear jean shorts with a pair of leather sheepskin boots.

They keep my ankles and feet snug.

If you follow my example, make sure you wear layers on top, including a puffer jacket.

On colder days, I like wearing a pair of tights under my shorts, which keeps my legs warmer overall.

This presents the best chance to wear fashionable ankle boots, or lace-up, sheepskin-lined boots.

For a slightly less casual winter look, swap the tights for pantyhose and wear knee-length boots.

You can change the tone of your outfit by wearing a pair of high tops with pantyhose or tights.

Of course, if you winter in the sun, then you’ll wear your jean shorts with espadrilles.

If you are going to spend time walking around the shops and outdoors, then make sure they are flat.

For a more fun feeling when you go out for lunch or coffee, choose a pair with a wedge heel.

Frequently Asked Questions about Jean Shorts

Can I wear boots with jean shorts?

Jean shorts leave just about your whole leg exposed, so wearing boots is a great option, especially if you want to draw attention to your footwear. Ankle boots in late summer and fall work well. In winter, you can opt for knee-length boots with tights under your shorts.

Do I have to wear flat shoes with jean shorts?

Jean shorts tend to be a fun and practical garment, so wearing flat shoes often goes with an active lifestyle. However, you can also wear wedges or even high heels with jean shorts, which will add to your legs and give the shorts some glamour.


Jean shorts can be worn with just about any color and any top. They can also be worn with really any style of shoe.

In Spring and Summer, your best bet is to wear flip-flops, flat sandals, or strappy heels.

In Fall and Winter, you can wear anything from sneakers, to ankle boots to sheepskin boots with your jean shorts.