Reviewed & updated: October 19, 2022 by Jamie Wilson BA
Plimsolls have long been a staple in most men’s wardrobes, but in recent years they’ve undergone something of a style evolution. Gone are the days when they were simply a casual piece reserved for quiet weekends – brands like Hudson and Religion are now producing a multitude of stylish plimsolls that you can rock on any occasion.
The likes of Vans and Converse are constantly dropping new collections too, with varying colours and textures providing a fresh perspective on the classic plimsoll look. If you’re feeling the love for these shoes but you’re not quite sure how to style plimsolls, then look no further than this guide. You’re welcome.
Jeans
Jeans are the perfect partner for your new plimsolls. Stay on trend with skinny jeans or keep your look current with a tapered pair by turning them up the ankle. Although pretty much any colour and cut of jeans will compliment your plimsolls, slim-fitting styles will help to show off your footwear and create a cool, yet casual look. This black pair of skinnys would look great with any style of plimsoll, as would this pair of Levi’s. The mid-blue wash on these Levi’s makes coloured or patterned plimsolls like these navy Superga pair really stand out.
Formalwear
Plimsolls have a reputation for being the king of casual, the go-to shoes for a night at the pub or dinner at your parent’s place. But they’ve grown up now and are ready to be taken out some place nice. Treat yourself to a pair of these Hudson leather slip-ons and you can sport the plimsoll look as formalwear too. Teaming this woven leather pair – available in both black and brown – with smart suit trousers like these ones makes for a suave look suitable for both the office and after-work drinks.
Patterns and Colour
If you’re the type who likes eye-catching but wearable pieces then look no further than a bright pair of plimsolls. Opt for a plain but bright pair like these pink Vans and team them with a crisp, simple t-shirt and trousers, then try and link up the colour again with accessories, maybe with your hat or your bag. You could go for a different colour all together in terms of your t-shirt and jacket, creating a blocked, structured look – just make sure your pieces all complement each other! Patterned plimsolls are on trend too.
This striped pair of Vans would look spot on with khaki or stone coloured shorts and a light top, especially if you were rocking a tan in the summer months. Another understated pattern can be found on this checked pair of Vans. The monochrome look is versatile and you so you don’t have to worry too much about it clashing with any other colours and patterns featured in your look. Despite their versatility, they are unusual and will be the focal point of your outfit. Whatever colour or pattern of plimsoll you choose, make sure they are in line with your look and help to express your overall aesthetic.
Clean and Simple
Bright colours and patterns are definitely a good look when it comes to footwear, but sometimes you just can’t beat a plain pair of cool shoes. Opting for a understated black pair of Vans or a sparkling white pair of Converse will provide you with a classic and versatile pair of plimsolls for your wardrobe, something that will complete almost every outfit. Keep your aesthetic clean and simple by pairing your plimsolls with a crisp white t-shirt and a pair of jeans.
Socks
Despite the fact that socks are, in some ways, quite a boring topic of conversation, they can actually make or break a look. Particularly if you’ve snapped up a coloured, patterned or textured pair of plimsolls, keep in mind whether they will look good with socks or whether you’d be better off sporting the old sockless look. While slip-ons generally look better without socks, many laced styles look pretty decent with a plain white or patterned pair, so think about those little guys if your outfit needs something to finish it off.
And on That Note
While plimsoll styles have evolved and their wearability has become more extensive, they still continue to give off a relaxed, I-don’t-care-vibe, whatever their pattern or material. Even if you’re having a go at the formal plimsoll look, keep in mind that this footwear style is somehow effortlessly cool and portray that through the rest of your look. With that advice, you won’t go far wrong.
