As someone who avoided wearing trousers for the best part of 20 years, I’ve always found it increasingly difficult to style them—particularly where shoes are concerned. Often, I’ll compile my looks from head to toe, starting with a statement top, the accompanying bottom half and then the footwear. However, I tend to find myself slipping on every shoe style I own (trust me—there are a few), unconvinced that any of them suit my strides.
Some prove too chunky, while others make me feel frumpy. Either way, it’s not a very enjoyable experience. As such, I set about to find out which shoe styles should be worn with which types of trousers once and for all. After lengthy try-on sessions and lots of IG scrolling, I think I’ve cracked the perfect footwear-and-trouser formulas. Below, you’ll find five key trouser silhouettes, each boasting three shoe options that work specifically with them.
Keep scrolling to see my edit of stylish shoes to wear with trousers.
Jeans make up the vast majority of our off-duty outfits, with straight-leg styles still proving to be increasingly popular. As far as shoes go, we think denim looks best paired with flats or low heels. For winter days, a pair of thick-soled boots will always serve you well, as the slim leg of the jeans will offset the chunky shape.
Honestly, there are few trousers these boots won’t work with.
This is the perfect heel height for days you know you’re going to be on your feet a lot.
Soon enough, we’ll be enjoying warm days, and styling our jeans sans socks.
Tailored trousers have diversified their role within our wardrobes from workwear to almost all occasions. When running errands, a pair of retro trainers will suit the current throw-back sneaker trends. If you’re embracing the polished silhouette for work, a pair of loafers will feel fashion forward, yet comfortable for all day wear. Finally, for dinners out, swap in a pair of mules to elevate the look.
Truly timeless.
A pair on every editor’s wish list.
The croc-embossed finish won me over.
If you’re stuck in a trouser rut, a leather version should be your first port of call. The fabric adds a nice contrast to all pairings, be it a simple black jumper or a crisp white tee. This versatile style is a another that does it all, from easy everyday looks, to the sharpest evening attire.
A designer gem.
Try mixing a contrasting shade with your black or brown leather trousers.
This pair adds a lot of polish for a reasonable price.
Wide-leg styles remain a favourite amongst the fashion set, and are on track to remain a winning silhouette for 2024. To contrast the oversized shape, play with a delicate ballet flat, or go bold with a bulky boot.
A favourite for 2024.
Ganni boots are a modern staple.
Colourful Adidas trainers are everywhere right now.
Leggings are an essential part of our uniforms, and have a wide range of occasions they can work for. Naturally, there’s a sporty feel that lends the style to trainer pairings, but don’t overlook the dress-up appeal of leggings. Make like Marilyn and try a bold heel to elevate this staple for evening, or a knee-high boot look that you’ll rewear for years to come.
A bold heel will definitely take your leggings from day to night.
The streamlined effect of leggings work so well tucked into knee-high boots.
Make the most of the sporty style of leggings with a chunky trainer.
Baggy jeans sit on the more statement end of the trouser spectrum, creating a voluminous silhouette that’s perhaps best balanced out with a slim, pointed-toe shoe. That being said, chunky loafers are another good option if you want to lean into the oversized look.
Show off your fashion know-how with these trendy boots.
Add red socks for a pop of colour.
I can’t believe these are only £35—bargain!
This post was originally published at an earlier time and has since been updated.
