How to Match the Right Shoes With the Right Suit

You don’t need to look too closely to realise menswear is full of rules. This is not necessarily a bad thing. While everyone should be encouraged to wear what they want, and many look good breaking each and every rule, for most of us, sticking to a few here or there will help us look our best.
This is certainly true of tailoring. The Rake has spent over a decade suggesting ways for you to learn, and then break, the rules of style. But, if you’re concerned with following tradition, and with sticking to the old ways, we’re here for that too. Pairing the right shoes with the right suit for example is nefarious business and one in which you should proceed with caution. There’s no use, after all, in spending your hard earned cash on a perfectly fitting two-piece and ruining the look with a pair of poorly chosen brogues. From breaking down each style to discussing colours and fabric, here’s how to match the right shoes with the right suit.








Oxfords
Oxfords are among the most formal of shoe styles. They are defined by their ‘closed lacing’, with the shoelace eyelets stitched into the vamp itself. This gives a supremely sharp, streamlined look, slimming the profile of the shoe and allowing it to conform closer to the shape of your foot. Oxford shoes typically come with a narrow last and a more sculpted silhouette, which combines for a smarter look.
As a result they work best with formal, business suits. Black Oxfords are the smartest of all, combining well with structured navy or grey suits. Brown pairs are slightly formal, and traditionally wouldn’t be seen in the world’s financial centres. They work best with navy and blue tailoring, and would be a good option for weddings. If you’re going to buy just one pair of shoes to wear with a suit, should it be the Oxford? “It’s what the rules would say”, says James Fox, brand director at Crockett & Jones. “But today, we sell more loafers than Oxfords to customers pairing shoes with tailoring. Life is more relaxed, and they are easy to slip on/off, comfortable to wear and far more contemporary than the more conservative Oxford. That being said, we still sell plenty of those too."
Derbies
Derby shoes are the less formal alternative to Oxfords. Their lacing is ‘open’, meaning the eyelet panels are sewn on top of the vamp. This eliminates the continuous unbroken line of the Oxford shoe, giving Derbies a chunkier profile and one that is usually more comfortable.
Furthering the more informal look is the fact that Derby shoes usually come with a wider last. The style’s heritage lies in walking and hunting, pursuits where comfort is prioritised as much as durability. Derbies then are better suited for those with wider feet, and they’re inherently more versatile too.
Loafers
There are many different styles of loafer. The best two, and the ones easiest to wear with tailoring are penny loafers and tassel loafers. Pennys originated in Norway in the 1930s, when they were first worn by farmers. They’re defined by their unique vamp, which has a cut-out that fits a small penny. Tassel loafers on the other hand come with a tassel tied at the front, as well as a slimmer, more elongated profile. “The most versatile shoe used to be the Derby, but today, it must be the penny loafer”, says Fox. “Dress it up with ease, and go for a cross-over colour like dark brown calf or suede. They are even comfortable to drive in. These days, we sell more dark brown suede penny loafers with rubber soles than classic Oxfords. Times have changed, but we’re enjoying the modern, versatile way of living. It gives us, as English shoemakers, the opportunity to produce a variety of different styles, increasing the depth of our collection that is sold around the world.” Both penny and tassel loafers are on the more casual end of the spectrum. So while they might look out of place with a pinstripe double-breasted jacket, they will work with a more laid back suit. Loafers look particularly good with soft, Italian tailoring. Think unstructured jackets and high-waisted, pleated trousers with little to no trouser break.
Suede shoes
Suede is an underrated option when it comes to footwear. Its soft, textured finish instantly makes a pair feel more relaxed, both stylistically and also comfort wise. It’s the ideal option for lightweight summer suits, made from cotton, linen, silk, or a blend of all three. Brown suede loafers are a particularly versatile option, and can work with virtually every shade of summer suit. Want to complete a linen suit for “a balmy summer wedding on the Amalfi coast? Any suede loafer, particularly from our unlined or unstructured loafer collection”, says Fox. “Available with leather and rubber soles. Rubber offers longevity and comfort. Leather, on the other hand, is traditional and perfect for when your inner Swayze makes an appearance.”