A guide to styling men’s shoes

Written by Nigel Simpkins

Men’s footwear is a huge market, with research from Mintel showing that men’s footwear accounted for 37% of all footwear sales in 2017. As such, it is clear that men have the money and time to buy themselves many pairs of stylish shoes, but how can you style them so that you look great and really make your new kicks stand out? Here are some top tips to help you look stylish in any kind of men’s shoes.

Work Boots

If you’re looking for comfortable footwear that will survive any terrain, then hardwearing work-style boots are the perfect options. There are so many hardwearing options that look fashionable and will stand the test of time, like Timberlands, which are renowned for their durability and have become popular with trendsetters thanks to their distinctive appearance. These boots are often best worn with outdoor wear, such as hardwearing clothes like corduroys, jeans and thick flannel shirts. If you’re keen to look more presentable then make sure your boots are clean and pair them with jeans for a smart casual look.

Cowboy Boots

Once considered to be just part of a fancy-dress costume, cowboy boots have come into their own over recent years and can now be worn as part of a relaxed rustic ensemble. Tough and rugged, cowboy boots now come in a range of styles and look great when paired with outdoor outfits.


Renowned for being paired with socks by out-of-touch older men, sandals are the ideal shoes for warm summer weather when you don’t want your feet to get sweaty. They’re ideal for the beach as they can be slipped on and off easily and are open so your feet can dry quickly after you’ve had a paddle in the water. Wear them with long shorts and a casual polo shirt to show off your relaxed style during the warmer weather.


A staple of anyone’s wardrobe, the humble trainer has become incredibly fashionable over recent years, meaning that you can now find comfortable, trendy trainers that you can wear anywhere. SSENSE offer a range of on-trend Fendi trainers that are perfect for pairing with any look, be it a casual office getup or a relaxed outfit for chilling out in.

Oxfords, Derbys and Brogues

These three styles of shoe are essentially the same, except that brogues are embellished with designs whilst oxfords and derbys are not. When it comes to the difference between the oxford and the derby, the key is in the way that the laces are secured to the shoe. All three styles are a classic, sleek shape that is ideal for wearing with a sharp suit. Usually made from leather, these three styles of shoe come in many colours including brown, dark blue and black. Pair any of the three styles with a more formal outfit to get a distinctive look or dress them down by wearing jeans and a neat shirt so that you appear casual but also smart.


Light, versatile and stylish, espadrilles come in a variety of colours and patterns meaning that they can be worn with a range of different outfits. A more casual style of footwear, they aren’t very hardwearing, so are best styled with relaxed outfits when you aren’t doing very much and just need to slip a pair of shoes on and off your feet quickly.


A stylish lace-less shoe commonly made of leather and designed to be worn as a casual suit shoe, loafers are great for a variety of outfits. This versatile shoe can be dressed-up to go with a suit or worn in a more casual way by wearing suit trousers and a shirt without the tie or jacket for those who want to appear casual yet still professional.


Similar to loafer and espadrilles, Moccasins are made from a single piece of leather wrapped around the sole of the shoe, and usually have a bow on the top and obvious stitching to the sides and top. Comfortable and relaxed, Moccasins can be styled with a lightweight summer suit or even worn with jeans in a more casual outfit.


This might sound a little odd, but ever since the rise in popularity of UGGS, men have been wearing slippers as outdoor shoes as well as in the comfort of their own homes. When wearing slippers out of the house, remember that they are strictly a casual shoe, so pair them with the most relaxed of outfits such as tracksuit bottoms and baggy t-shirts. They’re ideal for when you’re just popping out to the shops or out to the front of the house to move the bins and can’t be bothered to put on proper shoes.

Final Verdict

Always keep your own personal style in mind and if you don’t feel comfortable then don’t wear it. You want to look and feel good in your new shoes, so follow these top tips and you can’t go wrong.