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
Honestly, there are few trousers these boots won't work with.
OPTION 2: Kitten Heels
This is the perfect heel height for days you know you're going to be on your feet a lot.
OPTION 3: Ballet Flats
Soon enough, we'll be enjoying warm days, and styling our jeans sans socks.
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
Try mixing a contrasting shade with your black or brown leather trousers.
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
Colourful Adidas trainers are everywhere right now.
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
A bold heel will definitely take your leggings from day to night.
OPTION 2: Knee-High Boots
The streamlined effect of leggings work so well tucked into 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
Show off your fashion know-how with these trendy 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
Maxine Eggenberger is Who What Wear UK’s deputy editor and has over thirteen years of experience in fashion journalism. She been creating engaging and elevated style content specifically for Who What Wear UK since 2018, covering runway reports, emerging trends, long-form features, self-styled shopping stories and columns, including her edit of the best new-in buys. She ensures the highest editorial standards are met across the site, leads the editorial team in their SEO strategy and keyword planning, works closely with the beauty team on content initiatives, represents the brand at industry events, and regularly contributes to social media, including her own Who What Wear UK TikTok franchise, French Style Fridays. Previously, Maxine appeared on ITV's This Morning in her own fashion segment and has interviewed countless celebrities—everyone from Victoria Beckham to Oscar winner Lupita Nyong’o.
Prior to Who What Wear UK, Maxine’s career began when, after completing her first-ever internship at Look magazine, she was offered a position on the brand's fashion desk. She accepted, leaving university a year early in the process. Her passion and natural talent for writing and styling meant she swiftly rose through the ranks to become the title's fashion news and commercial content editor, with a stint as InStyle.co.uk’s fashion and beauty writer along the way. She later served as Look’s acting Editor in Chief, overseeing both print and digital, before embarking on a successful freelance career, working with Grazia, The Pool, and Marie Claire amongst others.
Maxine is based remotely from her countryside home near Edinburgh where she spends her downtime renovating her house, walking her dogs, hosting friends and trying to master the art of making Old Fashioned cocktails.
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