How To Wear Jeans With Boots

The jeans and boots combination is a staple for every Autumn/Winter wardrobe. A common feature of utilitarian workwear-inspired fashion, the chunky boots and jeans trend has been around for some time, and it’s not going anywhere soon. 

So, how do you get on board? How should you pair your jeans and boots? Which brands should you be wearing? Don’t worry; we have you covered with our handy guide that features tips and tricks from our style experts at Stuarts. 


Cuff or no cuff? 

When wearing jeans with boots, you should consider the length of the denim compared to the boot height. You want to show off your boots, but you don’t want the jeans to sit too high on your legs. 

You can layer your jeans and boots in one of two ways; stacking or cuffing. Stacking your jeans simply means letting your jeans bunch above the shoes and is suited towards skinny and slim tapered jeans. Cuffing your jeans is ideal for boxier fits with selvedge denim and straight regular-fitting ensembles.

How to cuff jeans with men’s boots

  1. Put your jeans on with your boots and roll your jeans over the bottom of your shoes. 
  2. From here, grab the bottom of your jeans and fold the hem back on itself with the aim of a 1.5-inch lip. 
  3. After you have rolled your jeans once, roll them again to keep them secure. 
  4. Make sure you only roll the jeans twice, as any more rotations will leave the cuff looking too bulky. 

Cuffing allows you to create a clean break between the end of your denim and the start of your shoes. One tip to consider is that the larger the cuff area, the shorter your legs will look. If you want to create the illusion of a longer leg, ensure your cuff isn’t too bulky. 

Colour combinations to choose when wearing boots with jeans

When deciding how to wear your boots and jeans, one particularly important thing is the colour choice of your pairing. You want to ensure that the colours work well together, and once you strike the right balance, the colour combination can take your outfit to the next level. Colour matching can make or break an outfit  – so make sure you opt for one of the following choices. 

Brown and blue 

When wearing boots, brown and blue complement one another perfectly. Opting for the blue and brown combination offers you versatility with your styling, as blue jeans are a wardrobe staple for any modern gentleman and can be dressed down for off-duty days or up with a crisp classic shirt. If you want to step up the styling further, try incorporating light earthy tones into the top half of your outfit with a jacket, overshirt or ‘shacket’. 

All black

The all-black combo will also go with a wide range of looks. Try tapered black jeans with black boots for a sleek look that will give you an unbroken trouser line. This look is great if you want to show off a statement piece on the top half of your ensemble. If you do decide to opt for the all-black look, we have a selection of black jeans in various fits to suit. 

Have fun with it

When choosing the colour combination of your jeans and boots, have fun with your pairing. Monochrome, tonal or all one colour are three main combinations to stick to, but it’s the confidence and styling of an outfit that will make it work. 

Denim brands to pair with boots

At Stuarts, we have a wide range of denim jeans for you to choose from in a selection of fits and colours to suit your existing wardrobe. Below you will find some of our favourites selected by our buying team, including understated brands and industry powerhouses. 

Naked and Famous

A distinctive denim brand that denim lovers rave about – Naked and Famous. Known for their cheeky references and innovative jeans, the selection of designs includes Japanese raw denim of the highest quality. Crafted in Canada, the Naked and Famous jeans range boasts scratch-and-sniff jeans, reflective denim and even glow-in-the-dark jeans. As a brand that prides itself on delivering quality to customers, a pair of Naked and Famous denim jeans will stay in your wardrobe for years and will be a great talking point at your next dinner party. 


Ever since 1890, Levi’s® has crafted high-quality denim that lasts. Every man probably has some form of Levi’s® in their wardrobe and the eclectic range available at Stuart’s are the perfect option for pairing with boots. Featuring classic styles, tapered and skinny styles to suit your aesthetic – you can’t go wrong. The Levi’s® range also includes various colours and washes to suit your existing wardrobe and take it to new heights. 

Edwin Jeans 

Established in Japan, Edwin Jeans offer some of the finest raw selvedge denim on the market. Combined with the finest craftsmanship and on-the-pulse styling, Edwin Jeans are an ideal companion for boots. Boasting boxy cuts and roomy fits, Edwin Jeans can be cuffed with boots to create a masculine silhouette ideal for dressed-down days. 

Boots to pair with jeans

If you already have a pair of jeans that you want to pair with boots but don’t know which on-trend footwear brands to try – we have you covered. Below is a selection of boot brands to bring your vision to life. 

Red Wing boots

For over 100 years, Red Wing boots have crafted the finest workwear-inspired designs, and their modern iterations feature hardwearing styles that look great and feel comfortable. Some stand-out styles within the range include the Classic Moc Toe Boot, which can be found in various colours. The chunky aesthetic of Red Wing boots offers a sturdy yet signature look combined with technical properties, such as Vibram® 430 Mini-Lug Outsole and triple stitched Goodyear welt. 

Blundstone boots

Full to the brim of choice, the range of Blundstone boots available at Stuart’s blends contemporary styling with traditional shapes. Crafted using recycled and recyclable materials, Blundstone boots are the perfect choice for the eco-conscious fashionista. Available in a selection of finishes and styles, you can be sure that Blundstone has a pair of boots waiting for you to pair with your jeans. 

Jeffery West boots

Jeffery West is the ideal brand if you’re looking for stylish boots to pair with your jeans. Quintessentially British, the designer has collated polished footwear crafted from premium leather designed to make you feel chic and sophisticated. Whether you wear them for the finer moments or weekend drinks, the collection is waiting to be added to your wardrobe. 

Find the perfect pair of jeans and boots at Stuarts London today

Browse the full range of men’s jeans and boots available at Stuarts London, where you will find the latest collections from premium brands that have been carefully selected. Whether you are looking for boxy-styled jeans that deliver the contemporary trend or tapered jeans that you can cuff – our stylists have curated a wide selection for you to choose from. You will also find many stylish footwear brands that will take your wardrobe to new heights. 

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