Jeans are an incredibly versatile piece of clothing and a go-to wardrobe staple, suitable for office and weekend looks alike. They may be basic, originally designed as hard wearing work wear, but jeans come in so many designs, styles, and colours that they can be worn in many exciting and stylish ways.

Despite their versatility, however, it can be a puzzle sometimes to work out how to match jeans with shoes. Pairing up a pair of your favourite jeans with an appropriate footwear pick needn’t be an unnavigable mire. Just follow our simple guide to picking shoes to wear with jeans and you’ll be putting your best foot forward in no time.

Styling shoes with jeans cheat sheet:

  • Wear a style of shoe or boot that suits the occasion
  •  If there is a style of jeans that works best for you then match it to an appropriate shoe to complete your look
  • Cuff your jeans to add extra flair and show off your shoes (but don’t roll them more than twice or you’ll kill the shape of your jeans)
  • Keep colour matching simple; dark shoes with dark jeans, and light shoes with light jeans – usually!

How to pick shoes to wear with jeans

How to wear trainers with jeans

It’s hard to put a foot wrong wearing jeans with trainers. It’s a streetwear staple that creates a sleek low-profile style that works with almost any pair of jeans, except maybe the dreaded bootcut.

Lighter coloured jeans call for lighter shades of trainers. Dark trainers with light jeans can create a dramatic contrast that draws the eye down. Lighter shades of trainers also look great with dark jeans, but you can also opt for a darker shade of sneaker to create a more balanced outfit.

Vans Black & White Old Skool Trainers

Adidas Gazelle Orange Trainers

Nike Air Force 1







How to wear derbies with jeans

Fashion may have shifted since their inception in the 19th century, but derbies have stayed loyal to their original design for over 100 years, and now create a casual alternative to their more formal Oxford counterpart.

With their chunkier, wider profile, derbies are good for counterbalancing denim. Try matching tapered or skinny jeans with a chunky pair of derbies for a casual and balanced look. Keep dark reds and black shoes for your black jeans and lighten the tone with browns and greys with your blue jeans.

Schuh Troy Gibson Derby

Dr Martens 1461

Base London Artist Derby







How to wear Chelsea boots with jeans

Much like other types of boots or smart shoes some basic principles apply to style Chelsea boots correctly. Chunky profiles are more casual than slim, browns are more casual than black, and suede is more casual than leather. Apply these rules to your choice of jeans (keeping skinny jeans with sleek Chelsea boots, and relaxed fit jeans with chunkier boots) and you’ll be well on your way to serving a smart and balanced look.

Dr Martens 2976 Base London Ramson Base London Engine Chelsea Boots







How to wear high-tops with jeans

Wearing jeans with high-top trainers couldn’t be easier. Just roll those jeans up to show off your latest sneaker purchase and you’re all set! Don’t roll your jeans more than twice though, or the resulting thickness of the cuff will create a chunky look that will throw off your whole look.

Converse All Star Utility Draft Boot

Converse All Star Chuck Taylor

Adidas Matchcourt x Beavis & Butthead







How to wear desert boots with jeans

Ever wanted to know the difference between a desert boot and a chukka boot? It’s all in the sole. A desert boot is a chukka boot with a crepe rubber sole, and typically a suede upper, as opposed to a Chukka boot which usually has a leather upper. Regardless of their subtle differences, desert boots and chukka boots have persisted as a popular choice for casual and formal occasions for decades.

Much like high-tops, wearing these boots with jeans couldn’t be simpler. Their versatility means they’ll go with anything from baggy to skinny jeans under the right circumstances. Just make sure to roll up the ankles of your jeans to show off your boots.

Red or Dead Mr Lawrence Desert Boots

Clarks Originals Desert Boots

Base London County Chukka Boots







How to wear chunky trainers with jeans

Chunky trainers, or dad trainers as they’re otherwise known, are a hot trend at the moment. The resurgence of 90s fashion trends might have seemed unlikely to those that lived through it the first time, but big trainers, loud prints, and straighter, wider jeans look like they’re going to stick around for a while at least.

To pull off the perfect 90s dad trainer look, go for a pair of jeans that match the decade with a wider, straighter fit and a lighter, stonewash colour.

Skechers D'Lites

Puma RS-0

Nike M2K Tekno







How to wear hiking boots with jeans

Wearing hiking boots with jeans can create a great workwear-inspired look, even if you’ve never done a day of hard work in your life.

To pull off the perfect casual lumberjack look, opt for a wide-legged jean to complement the chunkiness of your hiking boots. Wearing skinny jeans will create an unbalanced look that may contrast too harshly. A pair of indigo jeans with some Red Wing boots is the perfect example of this look, especially when you roll up your jeans with an oversized cuff to exude maximum vintage vibes.

Timberland 6 Inch Premium Boots

Red Wing 6 Inch Classic Moc Toe Boots

Dr Martens Bonny Boots







Ready to put your new found knowledge to the test? Take a look at our men’s footwear and get a new pair of shoes to match up with your wardrobe.