How To Wear 4 Different Trouser Styles
How To Wear 4 Different Trouser Styles

How To Wear 4 Different Trouser Styles

Ever wondered where your jeans should sit with ankle boots? Or perhaps you want to make a tailored trouser look less formal? From 90s cuts to split hems, here’s what you need to know about styling four types of trouser…
By Polly Sayer

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Do… Consider your footwear. You can’t go far wrong with a cropped straight-leg jean, but there are couple of things to bear in mind to ensure they look right. Cropped lengths look better with ankle boots – just make sure the gap between the top of the boot and hemline of the jeans isn’t too wide. Ideally, the jeans should sit just below the top of the boots, as a continuous line will give the illusion of a longer leg. 

Don’t… Team cropped lengths with a ballet flat. While you won’t get any strange looks, the overall effect is a little dated. Instead, go for a slightly longer-length jean that hits at the ankle bone – not only will this appear more modern, it will help your legs look longer, too. 


Do… Juxtapose a smart trouser with a casual shoe, like a pair of trainers. Smarter shoes like loafers and heels work for the office, but a sneaker lets you wear them in a more laidback way. When it comes to the shape of the trouser, a looser, longer fit should almost skim the floor (ideally a bit of fabric should bunch round the ankle). If you prefer a cropped length, opt for a straight, cigarette or tapered shape, avoiding anything too skin-tight. 

Don’t… Team a tailored trouser with a chunky, flat boot, as the combination feels a little too boyish. Instead, switch them out for a heel, whether it’s a boot or a court shoe – a more feminine footwear choice will balance out a masculine trouser. 

90s Length 

Do… Wear them day and night. Cropped length trousers have dominated for years, so it’s understandable if you’re apprehensive about making a longer 90s style work. Fortunately, they’re easier to style than you think – plus, they’ll make your look feel a little more contemporary. If you’re a ‘jeans and nice top’ kind of girl, don’t be afraid to wear them with a strappy heel for a night out. For the daytime, add a retro sneaker to refresh the classic ‘jeans and trainer’ combination. 

Don’t… Pair them with chunky, flat boots. In a similar way to tailored trousers, the combination feels a little too masculine and can be tricky to pull off. 

Split Hem 

Do… Make sure they’re long enough. Ideally a split-hem legging or trouser should be at least as long as the widest point of your ankle. If you’re wearing them with trainers, a slightly longer length works better as it’ll make your legs look longer – just make sure it finishes at least a couple of inches above the ground. If you’re wearing a heel, you can get away with something a little shorter. 

Don’t… Choose anything too cropped. A split hem should be sleek and elegant – a length that cuts you off at the wrong point will make your look feel disjointed.

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