What Shoes To Wear With Every Style Of Trousers

If you’re wondering why you don’t see more men wearing puffer jackets to the beach or putting sriracha sauce on their ice cream, the answer is simple. Some things simply should not and do not and go together.

The same goes for shoes and trousers. Sure, you’re probably well aware that flip-flops aren’t the perfect foil for a tailored three-piece (unless you want to be forcibly ejected from every wedding/job interview/funeral you ever find yourself in), but other footwear pitfalls are less obvious.

To take the guesswork out of it, here are the most common trouser styles and the shoes you should be matching them with.

What Shoes To Wear With Jeans

Jeans are the default for most men these days. These are trousers that go from weekend to work, and are so ubiquitous they’ve become almost background. Which should mean they go with any shoes. But that’s not so.

Smart jeans exist, but there are no jeans so smart that they look good with smart shoes. Leave denim and Oxfords to indie bands and your boss on a staff night out. Chelsea boots are generally as polished as you can pull off.

If your jeans are the kind of distressed, stacked versions Kanye might wear, they should be worn with trainers – minimalist always works, but chunky, statement styles work well if the jeans they’re with are more sober. Straight, heavy selvedge that harks back to hard men who did hard work in hard denim, however, works better with thick-soled boots than Yeezy 350s.

Men's Jeans and Footwear Combinations Outfit Inspiration Lookbook

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ADIDAS ORIGINALS Stan Smith Recon Leather Sneakers - click to buyNIKE AIR MAX 95 Sneakers - click to buyKURT GEIGER SLOANE CHELSEA BOOT - click to buyRED WING SHOES 875 Moc Leather Boots - click to buy

What Shoes To Wear With Tailored Trousers

A decade ago, the only choice at the bottom of your suit was how much break you wanted on your shoes. Then designers got creative, and the suit stopped being a uniform. Now you can split your jacket and trousers, you can wear a double-breasted jacket undone, and you don’t have to wear black Oxfords or Derbies. Although, of course, you still can – and if you’re heading somewhere formal, you probably should.

If you’re not, you know those white, minimalist sneakers that have been unavoidable for the past decade? Well, they’re tailoring’s new best friend. A slight gap between the trousers and shoes helps accentuate the split between smart and casual.

If your trousers have some texture – think tweeds, heavy wools or even flannel – they require weightier footwear. Brogue or pebble-leather boots provide appropriate heft, or go all in with a pair of boots that look like you might climb a mountain in, even if you’re only heading to the pub.

Men's Suits and Footwear Combinations Outfit Inspiration Lookbook

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STEMAR RS TOECAP OXFORD - Click to buyCHURCH'S Dubai Polished-Leather Oxford Shoes - Click to buyZESPA ZSP4 APLA SNEAKER - Click to buyCHEANEY Richmond Pebble-Grain Leather Boots - Click to buy

What Shoes To Wear With Chinos

Preppy trousers deserve a preppy shoe. If JFK might have worn it, then so should you: canvas sneakers in summer, duck boots in winter and, all year round, loafers, worn with or without socks as the weather dictates.

If that’s all a bit too Ivy League for you, then brogues add a couple of years to your look. Let the weight of your cotton dictate the chunkiness of the shoe.

Winter fabric deserves an equally robust shoe. Hiking boots are now a trend, even for the kind of man who defines ‘adventure’ as being more than five minutes from a decent martini. Avoid endless eyelets and garish nylon uppers. Stick to the kind of polished leather real climbers haven’t worn for a century. Show them off by rolling your chinos just above a pair of thick, woollen socks.

Men's Chinos and Footwear Combinations Outfit Inspiration Lookbook

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Dune Radiate Brogue Shoe - Click to buyBass WEEJUNS LARSON PENNY LOAFERS - Click to buySUPERGA 2750 COTU CLASSIC SNEAKER - Click to buyFRACAP M120 RIPPLE SOLE SCARPONCINO BOOT - Click to buy

What Shoes To Wear With Joggers

Fashion is so often impractical that when a trend like joggers comes round – comfortable, affordable, so versatile that you no longer need to think about what to wear every morning – you should hold it close.

Sportswear roots and a tapered cut make them the perfect foil to statement trainers. Feel free to indulge your space-age tastes in the knowledge that those slim, neutral joggers ground the look.

Dressing up options are more limited. High-low dressing might be trending, but there’s a line. Dress shoes and joggers passed it a couple of horizons ago. Chukka boots are about as smart as joggers can stand – suede adds some texture but, since the shoe was invented for playing polo in, they still feel sporty enough that the look doesn’t jar.

Men's Joggers and Footwear Combinations Outfit Inspiration Lookbook

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VANS VAULT OG CLASSIC SLIP ON LX - Click to buyNIKE TAILWIND 79 trainers - Click to buyDIADORA N9000 H ITA trainers - Click to buyclarks Desert Boot - Click to buy

What Shoes To Wear With A Tuxedo

It doesn’t pay to play too much with black tie. Even Jared Leto knows that you can try cyan jackets and bejewelled accessories up top, but a solid pair of shoes will always anchor your experiments.

If you want to make a statement, opt for a pair of bowed slippers, in either velvet or patent leather (match the texture to your matte or shiny bow tie). To make it louder, try an embroidered upper.

If you’d rather not field questions about your shoes all evening, stick to classic patent leather lace-ups. Or, in a pinch, mirror polish your Oxfords until they glow.

Men's Tuxedo and Footwear Combinations Outfit Inspiration Lookbook

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dune Shilling H Formal Shoe - Click to buyalexander mcqueen PATENT LEATHER SLIPPER - Click to buyGEORGE CLEVERLEY Albert Velvet Slippers - Click to buychurch SOVEREIGN CROWN SLIPPER - Click to buy

What Shoes To Wear With Shorts

The majority of shorts are inherently casual. So, as a general rule, your shoes should be too. However, that doesn’t give carte blanche to schlep out of the house having stuck any old battered running shoes on your feet.

The expanse of space between your hem and your laces does not aid your efforts to wear brogues. Instead, stick to trainers – preferably smart styles in premium materials so people won’t think you’re off to play squash – or summer-specific silhouettes like espadrilles, deck shoes or sandals.

If you can’t bring yourself to be shod in anything other than leather, opt for tailored shorts that are cut as well as your suit trousers, which opens up the options to include penny loafers. Just make sure to lose the socks.

Men's Shorts and Footwear Combinations Outfit Inspiration Lookbook

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CONVERSE CHUCK 70 OX RENEW trainers - Click to buyGRENSON Suede Penny Loafers - Click to buyORLEBAR BROWN Haddon Logo-Embossed Slides - Click to buyBIRKENSTOCK ARIZONA - Click to buy

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