Not All Shoes and Trousers Go Together, But These Combinations Sure Do

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.

1. STRAIGHT-LEG JEANS

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.

OPTION 1: Chunky Boots

OPTION 2: Kitten Heels

OPTION 3: Ballet Flats

2. TAILORED ANKLE-GRAZERS

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. 

OPTION 1: Loafers

OPTION 2: Retro Trainers

OPTION 3: Mules

3. LEATHER TROUSERS

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. 

OPTION 1: Flat Black Boots

OPTION 2: Slingbacks

OPTION 3: Heeled Boots

4. WIDE-LEG TROUSERS

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.

OPTION 1: Ballet Flats

OPTION 2: Chunky Boots

OPTION 3: Coloured Trainers

5. LEGGINGS

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. 

OPTION 1: Bold Heels

OPTION 2: Knee-High Boots

OPTION 3: Chunky Trainers

6. BAGGY JEANS

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.

Option 1: Pointed-Toe Boots

Option 2: Lug-Soled Loafers

Option 3: Court Shoes

This post was originally published at an earlier time and has since been updated.

Next Up: The 10 Major Trends That Will Define Spring 2024 Fashion