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Black Shoes

In almost every circumstance, black shoes are the smartest version in any category. “A pair of black Oxfords is probably the most dressed-up shoe you can have in your wardrobe,” says Luke McDonald, stylist at men’s online styling service Thread. “And that limits what other clothes you can wear them with.” You can think of them a little like a black blazer; they look great dressed up, but try them with jeans and you begin to look like a street magician.

To start from the top down, black should be your go-to for black tailoring, whether you need something for black tie or just a formal work shoe. “They also team well with grey or charcoal tailoring, particularly in more formal offices,” says McDonald. Despite what some folks think, wearing black with blue won’t bruise your sartorial ego, although stick to darker shades of navy rather than something more celebratory, like royal blue.

Casual trousers are trickier. If you’re going to wear black shoes with chinos in the brown spectrum, then stick to less formal styles. “A Derby looks better than an Oxford as it’s a bit chunkier and more relaxed,” says McDonald. The same goes with jeans. “Oxfords would only ever work with very slim black jeans and even then you’re going to look like a forgotten member of the Libertines.” If you insist on black shoes with your dark denim, then it’s best to go for something like Chelsea boots or Dr. Martens.

If you’re the kind of guy who likes his chinos colourful, then the sudden shift to black shoes can feel a bit severe. You can lessen the impact by cuffing the hems and even losing the socks, and making your shoe style as dressed-down as possible – loafers are preferable to anything with laces.

Finally, you should probably avoid shorts and black shoes once you’re out of school uniform.

The right trouser colours to wear with black shoes

Brown Shoes

Brown is the most forgiving shade of smart shoes. The breadth of browns available means that there’s a tone for almost any situation, bar the very smartest offices; even a pair of bespoke chocolate John Lobbs will have you blackballed in some investment banks. But with anything other than a black suit or tuxedo, brown shoes add personality and feel a touch less stuffy.

“The lighter the shade, the more relaxed the look,” says McDonald, “particularly if you add detail, too.” A pair of brown brogues are less formal than the same shade Oxfords, for example.

Away from tailoring, brown should be your go-to for chinos of any colour, although be careful not to match too closely; like with double denim, you want at least two shades of difference between your trousers and your shoes, lest you look like you’re wearing the bottom half of a onesie.

Darker browns look great with indigo denim, but can work just as well with more washed out shades. Just make sure that you step down into a less formal style – suede Chelsea boots are perfect, as are chunky brown worker boots.

Black jeans and brown shoes is a minefield of differing opinion and one not worth marching into if you’ve any personal doubts. But if you’re confident, then it’s a look that can work, so long as you stick to shoes in a shade that’s nearer black than tan. Although again, boots are easier to pull off, here, particularly Chelseas, which give you the air of someone who’s just left One Direction to find a direction of their own.

The right trouser colours to wear with brown shoes and boots

Oxblood Shoes

Though technically a colour, oxblood can act almost as a neutral. They tend to work in almost exactly the same way as brown, although because they’re a touch bolder, they tend to lend whatever you’re wearing an ounce or two more personality. “Making a statement with smart shoes shouldn’t mean going too far out of your comfort zone,” says Vieira. “Instead of opting for an extravagant style, it could be as simple as integrating new colourways in silhouettes you already wear on a daily basis.”

That said, it’s still easier to pull off oxblood if you dress them down a touch; Derbies are a more versatile choice than Oxfords because, while they won’t work with your smartest suits, you can wear them with everything from navy tailoring to jeans and chinos. That said, if you live in suits, a pair of burnished, oxblood Oxfords, with a Berluti-style patina, can be a distinctive way to make them feel more varied. They’re particularly good for making your workwear wedding-ready.

Casual styles offer much more leeway. The oxblood penny loafer is a classic and can be your summer go-to with anything from light-wash denim to tan, navy and even colourful chinos. Ditch the socks and cuff the hems for a Dickie-Greenleaf-on-the-Riviera feel.

The right trouser colours to wear with oxblood shoes and loafers

Tan Shoes

Tan is brown’s most casual tone. “It’s best on more relaxed styles like brogue Derbies or boots,” says McDonald. “Tan suede shoes can also look good, but you need to wear them with fairly informal outfits.” In smarter styles, tan is a good way to personalise an outfit – the kind of look-at-me tailoring that pervades Pitti Uomo is often accessorised by a tan loafer or brogue. It’s a particularly good anchor for brighter shades of blue or to take the stuffiness out of patterns like pinstripes.

Tan works well with jeans of all shades and chinos of any colour, especially in summer when they serve to lighten your look up a bit. You can even get away with wearing tan shoes with shorts, particularly if you go with something laceless like a penny loafer or something with texture, like suede.

The right trouser colours to wear with tan shoes and boots

Blue Shoes

Blue can be an uncomfortable colour for smart shoes – though it’s a staple neutral everywhere else in your wardrobe, shiny blue leather tends to look a little try-hard. Once you step into more casual styles, however, blue is a perfect way to add some personality to looks. Textured leathers like nubuck work well in navy, says Vieira, and can even be worn as a pop of unexpected colour in black casual outfits.

Like nubuck, suede is an Elvis-approved way to pull off blue shoes; the raised nap adds a depth that you don’t get with leather, which makes blue shoes seem considered rather than flashy. So long as you don’t try to dress them up too far, blue suede brogues work well with any colour of suit (so long as it’s not black) and the same for chinos, particularly with an ankle-flashing roll.

More casual still, navy is perfect for desert and chukka boots, especially since it’s dark enough not to show rainspots if you do get caught in a shower. “Both styles look great with jeans,” says McDonald. “They’re rugged, but still smart enough for a nice restaurant or bar.” But again, try not to match your shoes and trouser shades too closely. If in doubt, use a brighter sock in a complementary shade, like red, to break things up a little bit.

The right trouser colours to wear with blue shoes and boots

White Trainers

When Common Projects launched its Achilles Low almost 15 years ago, the Italian-American shoe brand helped cement a new category in menswear; the sneaker that acted like a smart shoe. Though all-white tennis shoes weren’t new – Adidas was already pumping out Stan Smiths, although not quite in the numbers they do post-Common Projects – they weren’t something that you could wear as easily with a suit as you could with denim shorts.

But now, so long as you get a completely clean pair, free from logos and crafted in premium leather, white minimalist trainers can be worn with just about anything (in the right context, of course; they’re probably not the best thing to pair with tailoring for partnership interviews at your law firm).

They’ll work with any suit, even black – although you’re best swapping the shirt and tie for something like a roll neck or long-sleeved polo – and look great with any pair of jeans, from premium Japanese selvedge to shredded stonewash. Same for chinos, for shorts, for parachute pants; whatever trousers you’ve got, white trainers will work.

In fact, the only tricky thing about white trainers is keeping them that way. “Box-fresh versions work with a suit,” says McDonald. “Battered, stained sneakers don’t. To keep them pristine, prep them with Crep Protect spray and then keep some babywipes in your bag or desk drawer for touch-ups during the day.

The right trouser colours and denim jeans to wear with white sneakers

Colourful Trainers

Where white trainers led, its brighter plumaged brethren followed. Time was that bold-hued sneakers were only for exercise. Now, they’ve crept from the streets into offices, an eye-catching way to show your affinity for the latest hype brand and Nike drop. “But all those colours make them much less versatile,” says McDonald. “In fact, they only really work with neutrals, unless you’re able to pull off some very advanced colour-matching.” Even then, you’re liable to leave onlookers with a migraine.

Because colourful trainers are so casual, you’re wisest sticking to jeans (anything from white to washed to black is fine), joggers (think grey, black or navy) or chinos (tan and navy are safest). “You should let your shoes do the talking,” says McDonald. “If they’re the brighest thing in your outfit, then they’ll draw the eye. If you have too many other bright colours, people won’t know where to look.”

The right trousers and jeans to wear with bold colourful sneakers

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