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 not so.

Smart jeans exist, but there are no jeans so smart they look good with smart shoes. Leave denim and black lace-ups to indie bands and your boss on a staff night out. Chelsea boots are as polished as you can pull off, and even then they’re tricky unless both jeans and boots are slim and black.

Most denim isn’t. If your jeans are the kind of distressed, stacked versions Kanye might wear, they should be matched with trainers – minimalist always works, but statement designs work well if the jeans they’re with are more sober.

Straight, heavy selvedge harks back to hard men who did hard work in hard denim. Thick-soled boots work better than Yeezy 350s.

Men's Jeans and Footwear Combinations Outfit Inspiration Lookbook

river island feb 2016river island 2016river island denim 2016forever 21 aw14

Key Styles

Men's Jeans Footwear Recommendations

sons of london chelsea boot - Click to buythorogood MOC TOE boot - Click to buyNIKE AIR MAX BW OG - Click to buyADIDAS STAN SMITH VINTAGE - Click to buy


A decade ago, the only choice at the bottom of your suit was how much break you wanted on your Oxfords. 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.

But if you’re not, or if you’ve got one of the new breed of unstructured suits that wears as well with a T-shirt as a collar, then experiment a little. Those white, minimalist sneakers that have been unavoidable for the past five years? Well, it’s partly because they’re your new tailoring’s new best friend. A slight gap between trouser and shoe helps accentuate the split between smart and casual.

If your suit has some texture – think tweeds, heavy wools or even flannel – it wants weightier footwear. Brogue or pebble-leather boots provide appropriate heft. Just avoid anything a man might actually climb mountains in.

Men's Suits and Footwear Combinations Outfit Inspiration Lookbook

Brunello Cucinelli ss16j.crew aw15burton aw16house of fraser ss16

Key Styles

Men's Suits Footwear Recommendations

PAUL SMITH Ernest Polished-Leather Derby Shoes - Click to buyREISS FENTON LEATHER OXFORD SHOES BLACK - Click to buyGRENSON SEBASTIAN BOOT - Click to buyKINGSMAN + George Cleverley Scotch-Grain Leather Boots - Click to buysuitsupply DOUBLE MONK STRAP - Click to buyCOMMON PROJECTS Original Achilles Leather Sneakers - Click to buy


Preppy trousers deserve a preppy shoe. If JFK might have worn it, then so should you: deck shoes 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

mango mangant ss14dunhill ss15nordstrom

Key Styles

Men's Chinos Footwear Recommendations

g.h.bass WEEJUNS LARSON PENNY LOAFERS - Click to buySPERRY TOPSIDER AUTHENTIC ORIGINAL 2-EYE - Click to buySperry Men's Avenue Duck Boots - Click to buyGrenson Stanley Brogues - Click to buyASOS Brogue Boots in Stone Suede - Click to buyDIEMME ROCCIA VET BOOT - Click to buy


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. Activewear 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. Juxtaposing high and low 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

river island aw16american eagle ss15j.crew 2014j.crew 2014

Key Styles

Men's Joggers Footwear Recommendations



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 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 patent leather lace-ups, polished until they glow.

Men's Tuxedo and Footwear Combinations Outfit Inspiration Lookbook

suit supply 2016sarar ss14sarar 2014gieves & hawkes

Key Styles

Men's Tuxedo Footwear Recommendations

oliver brown Patent Dress Shoe - Click to buysuitsupply TUXEDO SHOE - Click to buyCHURCH Velvet crown loafers - Click to buyGEORGE CLEVERLEY Tassel-stitch velvet slippers - Click to buy


Shorts are inherently casual. So your shoes should be too.

The expanse of leg between hem and laces does not aid your efforts to wear brogues. Instead, stick to trainers – smart styles mean people won’t think you’re off to play tennis – or summer-specific silhouettes like espadrilles, deck shoes, sandals or pool sliders.

Just make sure to lose the socks.

Men's Shorts and Footwear Combinations Outfit Inspiration Lookbook

mango man ss15selected homme 2016el ganso ss15crew clothing ss15

Key Styles

Men's Shorts Footwear Recommendations

NIKE MATCH CLASSIC - Click to buyZESPA X CHARLES F. STEAD ZSP4 SNEAKER - Click to buyBIRKENSTOCK MILANO - Click to buyADIDAS ADILETTE - Click to buyASOS Espadrilles in Grey Canvas - Click to buysperry AUTHENTIC ORIGINAL WASHABLE 2-EYE BOAT SHOE - Click to buy