How to match your shoes to your outfit

The rules of footwear, like most things in menswear, have grown less rigid in recent years. These days you can wear trainers with a suit and Oxfords with jeans. But the real key to matching your shoes to your outfit is getting your colours right. As with everything else you wear, nailing colour combos is both the easiest and the hardest thing about putting together an outfit. It’s very easy to play it safe – black shoes with black trousers, brown shoes with tan chinos etc – and never put a foot wrong (pun intended). But that can get very boring, very fast and unless you only ever intend to wear a couple of colours of trousers, you’d need to invest in a rainbow of footwear options to keep things interesting. Thus, footwear should be treated as an integral part of your wardrobe. For any footwear novices out there, here are some basic tips to help guide your shoe selections.

The Basics

Before breaking things down by colour, here are some hard and fast rules that should make things a little easier to follow.

First of all, smart shoes and trainers obey different rules. A white pair of smart shoes would look very weird, but clean white trainers will work with pretty much anything. If you’re wearing something bright on your feet, then try to anchor them by wearing neutrals elsewhere. Bold shoes won’t make much of a statement if you’re wearing a shirt covered in pineapples and palm trees. Generally, though, darker tones are more versatile than lighter and a hell of a lot smarter. Block colours are also smarter than anything multicoloured. And finally, it doesn’t really matter what colour your shoes are if they’re dirty and or scuffed. Cleaning and preservation products aren’t just a gimmick and are definitely worth investing in. For your smart shoes, find a polish that matches the colour, or a neutral polish and keep them in good nick.

Trainers

As long as they’re completely clean, free of brand logos and made from leather, white minimalist trainers can be worn with just about anything (within reason, of course; probably best not to wear to them to a job interview for an accountancy firm). Clean white trainers will work with pretty much any suit – although you’re probably better off swapping the shirt and tie for a polo or a roll neck – and look great with jeans. Same goes for chinos, shorts, joggers; pretty much whatever you’re having, white trainers will work. The only problem with white trainers is keeping that way. Box-fresh will work with anything, tatty and stained won’t. As already advised, prep them with Crep spray and treat stains as soon as they happen with wipes. Try to avoid washing machines and definitely don’t put them in a tumble dryer.

Colourful trainers are mess less versatile than their angelic brethren. In truth, they only really work with neutrals. Because they’re so casual, you’re better off sticking to jeans or joggers and letting the shoes do the talking.

Black Shoes

In most circumstances, black shoes are the smartest option available. A pair of black Oxfords are probably the most dressed up shoe you’ll ever need but they limit what other clothes you can wear with them. They’ll look great with a suit, but try wearing them with jeans or joggers and you’ll look like a secondary school student who forgot it was a non-uniform day. Black shoes should be your go-to for tailoring, whether it be a special ‘black-tie’ occasion or simply a formal work shoe. Casual wear is a lot trickier though. If you’re going to wear black shoes with chinos then go for something less formal like a Derby or a Chelsea Boot. If you’re into wearing colourful chinos, then the sudden shift to black can feel a little jarring. Losing the socks and rolling your trousers will soften the severity but you’re really better off picking an alternative shoe colour. Unless you intend to start a post-punk indie garage band, then avoid black shoes with jeans at all costs.

Brown Shoes

The number of different shades available means that there’s a brown shoe that will work with almost any outfit, bar the most formal of occasions; even the most expensive pair of brown shoes you can buy won’t fly with a tux. The lighter the shade, the more relaxed the look, particularly if you add detail. Brown Oxfords are much more formal than brown brogues for example. On the casual side of the coin, brown can be your go-to for chinos. They’ll work with pretty much any colour of chino but be mindful not to match colours too closely. You’ll want a shade or two in the difference so you don’t look like you’re wearing part of a onesie. Brown footwear works great with denim, but again, make sure you step down to a less formal style like a brogue or a boot. Darker Browns work particularly well with indigo jeans.

Tan Shoes

Tan is the most casual shade of brown you can wear and works best for more relaxed styles like derbies or loafers. In more formal settings, tan shoes can have a ‘look-at-me’ effect, which is fine if that’s what you’re going for but that can sometimes be counterproductive. NEVER wear tan shoes to a job interview though. Tan works jeans and chinos of any colour and can lighten up a look by adding some colour. Tan shoes have gotten a bad rap in recent years but they can still add to a suit or a casual outfit so long as you stay on the browner side of tan and avoid the bright orange variations.

Burgundy/Oxblood Shoes

Burgundy or Oxblood shoes can almost be considered neutral. They work in much the same manner as brown just they’re just that little bit … bolder. While they do work well with tailoring, it’s still much easier to pull off burgundy if you dress them down a little. They’re also particularly good at making work-wear wedding appropriate by adding a dash of personality.

Blue/Navy Shoes

Blue shoes are becoming more and more common these days. For smarter looks, they can seem a little peacocky so again I’d advise erring on the side of casual. Blue is a great way of adding some personality to an outfit. Blue suede is an Elvis-approved way to add a little depth to a look that seems considered rather than flashy. So long as you don’t try to dress them up too far, blue suede shoes will work with tailoring (except for black), jeans of all shades and chinos of any colour.