How to wear slip-on shoes


Loafers are comfortable, versatile and smart.
Image source: Samuel Windsor

Slip-ons are the height of hipster fashion, but they’re also a great choice for a whole range of formal, smart-casual and relaxed occasions. Plus they’re a superbly comfortable and easy-to-wear alternative to lace-ups. From penny loafers to moccasins and boat shoes, here’s your guide to looking the ticket in slip-on shoes.

In fashion


Loafers might be cutting edge fashion, but they’re also effortlessly timeless
Image source: Shutterstock

Check out any recent copy of GQ, or any other men’s fashion magazine for that matter, and you’ll be greeted by images of stylish gents sporting figure hugging suits. They’ll be wearing cuffed trousers to better display the wearer’s ankles, and dangling at the end of them, a very stylish pair of loafers.

It’s always nice to know you’re at the cutting edge of fashion, even if you’ve had to wait thirty years for the wheel to turn full circle. But slip-ons are all the rage, and here’s how to make the most of it.



A smart pair of black leather penny loafers works well for the office or formal occasions
Image source: Samuel Windsor loafers

At the smarter end of things, you have penny loafers, tasselled loafers, and horsebit loafers – the ones with the metal bar across the apron. Available in leather or suede, these make excellent shoes for formal occasions like weddings, graduations, and evening soirees.

Loafers may not be your first thought for a day at the office, but a smart black pair does make the grade provided you wear them with sober and professional-coloured socks.

The same slip-on also does smart casual very nicely, and for less formal occasions, feel free to add to the list of acceptable choices. Moccasins and boat shoes both work well for dress-down events such as barbecues.

Driving? Give your feet a break by ditching restrictive lace-ups in favour of a luxurious pair of soft leather or suede driving shoes. The slim-fitting profile and rubber sole gives great feel when you’re operating the foot pedals and the flexible leather minimises the stiffness you’ll feel at the end of a long journey.

How to fit a slip-on


Suede tasselled loafers with a high apron are easy to slip on but offer a snug fit
Featured: Prestige Tasselled Suede Loafers from Samuel Windsor

Slip-ons are designed to show more of your foot and ankle than standard lace ups. You don’t wear them with thick woolly socks, so make sure before you try yours on, that you’re wearing an appropriate pair of ankle socks.

Stand up and have a walk around. The ball of your foot should fit nicely into the widest part of the shoe, and when your weight is on your foot, your longest toe (sometimes your second toe) should come no closer than 1/2” from the front of the shoe. At the heel, the shoe should neither slip nor pinch. Happy with your purchase? Let’s take a look at your wardrobe options.



Brown suede loafers are perfect with chinos
Image source: Samuel Windsor

For trips to the theatre, meals out, and other special occasions, loafers offer the chance to make a subtle statement. Wear your brown penny loafers with a pair of classic chinos or cavalry twill trousers. A smart weekend shirt and sports jacket or blazer completes the look.

For something a little different, stick with your chinos, add a crisp white, pale blue or pink cotton shirt and tweed jacket, and put on a pair of luxurious suede loafers. Feel free to experiment with colour – light khaki chinos go well with blue, green or even red suede slip-on shoes.

Feeling the chill? Opt for wool mix or tweed trousers. Go for darker winter colours, worn with black loafers or alternatively, contrast dark blue and grey trousers with brown loafers. Wearing winter textures? Don’t overdo it. If you’re into suede shoes, keep your trousers untextured. Wearing moleskins? Go for leather footwear.



Driving shoes offer the ultimate in comfort and style
Image source: Samuel Windsor

Having friends around? Driving to your local for a bite to eat? Moccasins are the perfect choice for when you want to relax and unwind. Wear yours with chunky cords, moleskins or jeans, and go for a thick fisherman’s jumper or Nordic-style sweater over a country check shirt.

Moccasins are all about comfort – think of that Scandinavian lifestyle buzz-word “hygge” which, roughly translated, means hanging out in front of the fire with family and friends. It’s slouching with style – all you need now is some aquavit and a scented candle or two, and you’re practically a hipster.

Deck shoes


Slip-on deck shoes are ideal casual wear
Image source: Samuel Windsor

It doesn’t matter whether you’re a yacht club regular or have no association with boats other than the occasional cross-channel ferry passage, deck shoes are a great look for casual spring and summer wear.

Probably the only slip-on that works a treat when you wear them with your shorts, this is the ideal look to go for when wielding the barbecue tongs. Just bung on a polo shirt or relaxed weekend check shirt, and you’ll look every bit the convivial, but well-dressed host.

Deck shoes also look good with chinos and jeans – it’s up to you whether you decide to bear your ankles or not, but we suggest that if you do, you invest in a pair of invisible ‘foot socks’ to help keep your feet comfortable, and your shoes smelling fresh.

How do you like to wear your slip-ons? We’d love to hear your fashion tips. Just head over to our Facebook page and drop us a line.

Posted in How To - Shoes.