Compared to fashion’s normal spin cycle, shoe trends move on a geological scale. Bar the odd interloper – we see you, pool slides – footwear sticks to the classics: trainers, slip-ons, lace-ups, boots. Where outerwear shifts seismically each season, shoes barely wobble the needle.

Which is why runway appearances shouldn’t rank too high on the list of features you look for in new shoes (and not just because, as Christopher Kane recently proved with his bejewelled Crocs, those appearances tend to be driven less by aesthetics and more by deeply uncool brands, with deeper pockets, after some catwalk cachet).

Instead, look to the trinity of build, comfort and versatility. Shoes are expensive. You will buy fewer than you do clothes. So invest in pairs that keep feet protected from weather, free of blisters and which you can rotate through at least a handful of outfits.

That doesn’t mean dull. You can consider this season’s move towards seasonless, minimalist clothes a blank canvas for experimental styles. At Prada, that meant chunky, puddle-clearing soles. At DSquared2, laces that extended almost to the toe cap. And at James Long, Refresher-tinged buckles and stripes. None of which will concern the seismologists overly. But all will keep this season’s looks from being too down to earth.


A menswear staple since Irish farmers punched holes in their shoes to let bog water out, brogues sit in that smart-casual sweet spot that takes the stuffy out of your suit, but dress up your jeans for lunch with your in-laws. “Craftsmanship and durability is essential for winter,” says Mr Porter footwear buyer David Morris.

‘Made In Northampton’ is shorthand for both – the town’s churned out the world’s best leather footwear since the Civil War and brands like Church’s, Tricker’s and Grenson ensure that reputation remains. The more broguing, the more casual the shoe – let whether you’ll deploy weekday or weekend dictate – but Goodyear welting is non-negotiable. “A Goodyear welt provides a solid structural foundation, which is imperative at this time of year,” says Morris. It also makes swapping the soles a cinch, which adds decades to your investment.

Though classic always works, the demise of #menswear means brogues have loosened up. “Brands have been experimenting with detailing to bring brogues more into casualwear,” says Kasia Katner, stylist at Thread. “Hybrid brogues, with wedges, crepe or a chunky commando sole, give this style a less formal feel, more reminiscent of workwear boots.” Prada even grafted on an air sole, which we’d advise keeping away from office and gym. But wearing everywhere else.

Men's Brogues Outfit Inspiration Lookbook - Autumn/Winter 2016 Shoe Trends

brooks brothers aw16scotch & soda aw16tods aw16j.crew autumn 2016

Key Pieces

  • Grenson Archie BrogueGrenson Archie Brogue
  • Churchs Grafton BrogueChurchs Grafton Brogue
  • Trickers Ilkley Pebble-grain Leather Wingtip BroguesTrickers Ilkley Pebble-grain Leather Wingtip Brogues
  • Churchs Mcpherson Textured-leather Wingtip BroguesChurchs Mcpherson Textured-leather Wingtip Brogues
  • Lace-up Shoes In LeatherLace-up Shoes In Leather
  • Grenson Archie Wedge-sole Leather BroguesGrenson Archie Wedge-sole Leather Brogues
  • River Island Brown Leather And Denim ShoesRiver Island Brown Leather And Denim Shoes
  • Ted Baker RACHET Brogue wingtip detail trainersTed Baker RACHET Brogue wingtip detail trainers
  • Tods Classic BroguesTods Classic Brogues

Lace-Up Boots

Menswear reminisces on its time in the ranks like a retired colonel three whiskies deep. Which makes ‘military’ a trend that never dissipates. This season’s version is less front line, though – gold embroidery, brocade and epauletted greatcoats, put through a punk filter by the likes of Casely-Hayford and Dries Van Noten. Think build quality that could handle no man’s land, but styled for the mosh pit, instead of the parade ground.

“John Lobb lace-up boots will last a lifetime,” says Morris. “Historically, they have been seen as a traditional shoemaker, but the ‘Alder’ boots draw upon a more modern design, especially from the combination of smooth and grained-leather.” For a 1990s vibe, swap the combats for slim black jeans or loose-fit trousers, says Lee Goldup, senior menswear buyer at Brown’s.

For those who pair plaid shirts with facial hair, not a copy of Nevermind, look to boots with a little extra detail. “Moc toes are featured across a wide range of styles this winter and brogue detailing is also popular,” says Katner. With jeans, think chukka or work boots; with trousers, military or brogue boots. “They’re ideal when it’s too cold for shoes, but you want to maintain a level of smartness.”

Men's Military and Work Boots Outfit Inspiration Lookbook - Autumn/Winter 2016 Shoe Trends

h&m 2016mango man 2016Brunello Cucinelli aw16massimo dutti aw16

Key Pieces

  • Marsell Military BootsMarsell Military Boots
  • Base London Clapham Leather Military BootsBase London Clapham Leather Military Boots
  • Sandro Leather BootsSandro Leather Boots
  • Tommy Hilfiger Dillan Stitched Detail Lace Up BootsTommy Hilfiger Dillan Stitched Detail Lace Up Boots
  • Dolce & Gabbana Perforated Suede Worker BootsDolce & Gabbana Perforated Suede Worker Boots
  • Shoe The Bear Worker BootShoe The Bear Worker Boot
  • Grenson Fred Brogue BootGrenson Fred Brogue Boot
  • Okeeffe Felix Waxed-suede Chukka BootsOkeeffe Felix Waxed-suede Chukka Boots
  • Clarks Originals Desert BootClarks Originals Desert Boot


Monk-straps – beloved of medieval monks, then no one, until mid-2000s suit obsessives made them street style catnip. When those hashtag dandies ditched tailoring for sportswear, their #dubmonks hit Oxfam. But this season, the strap gets another run-out.

“The most classic monk-strap has two straps, but in recent seasons more styles have featured a chunkier one-strap or even triple straps,” says Katner. “They’re a great winter option if you’re looking for a slip-on look, but it’s too cold for loafers.”

The variety of strap styles means there’s a lot to play with; the right pair can be an expert bridge between office and cocktails. “For a smart look, opt for the classic double-strap in polished leather. They work really well with contemporary tailoring.” Keep fits slim and your trouser break minimal to flash the buckles.

Even if you’ve ditched tailoring entirely, there’s still life in its partner. Ideal for winter, monk-boots hark back to the monastic originals; slouchy in style, but updated with a double or triple strap and a textured sheen on the leather. Just swap the robes for distressed denim and an oversized sweatshirt.

Men's Monk-Strap Shoes Outfit Inspiration Lookbook - Autumn/Winter 2016 Shoe Trends

four five club aw16brooks brothers aw16Brunello Cucinelli AW16burton aw16

Key Pieces

  • Reiss Finn Double Monk Strap Shoes BlackReiss Finn Double Monk Strap Shoes Black
  • John Lobb William Leather Monk-strap ShoesJohn Lobb William Leather Monk-strap Shoes
  • Churchs Monkton Double Monk BrogueChurchs Monkton Double Monk Brogue
  • Santoni Monk Strap BootsSantoni Monk Strap Boots
  • He By Mango Leather Monk-strap ShoesHe By Mango Leather Monk-strap Shoes
  • Aldo Hondo Leather Monk BootsAldo Hondo Leather Monk Boots
  • Magnanni Vidal Double Buckle BootMagnanni Vidal Double Buckle Boot
  • George Cleverley Thomas Leather Double Monk ShoesGeorge Cleverley Thomas Leather Double Monk Shoes
  • Allsaints Arc ShoeAllsaints Arc Shoe

Derby Shoes

The Derby, like the Oxford, is ubiquitous. Unlike the Oxford, it has an open lacing system, which makes it a touch less formal. For AW16, the more relaxed lace-up went wild. “They lend themselves to the classic brands such as Tricker’s and O’Keeffe,” says Morris, “but the designer brands have reinterpreted the style this season, especially Prada and Tod’s.”

Huge, rubber soles raise Tod’s Derbies off the ground – just as well, to keep grime off the cherry red vamp. They transform them into a boot-Derby hybrid, giving them a statement edge that summer versions just can’t match.

“Derbies are a classic style that has been transformed through statement colours and effects like worn leather and varied textures,” says Katner. “If they’re patent, with a cap toe, stick to formal eveningwear. But if they’re a simple staple colour in a plain finish, they can be dressed up or down to look smart or smart-casual.”

The more detail – big soles, odd colours – the further down they’ll dress. For a casual look, wear with woollen trousers or jeans and an overcoat. If your shoes are plain, pair with suits or tailored separates.

Men's Derby Shoes Outfit Inspiration Lookbook - Autumn/Winter 2016 Shoe Trends

scotch & soda aw16Brooks Brothersclosed aw16mango 2016

Key Pieces

  • Cheaney Deal Burnished Pebble-grain Leather Derby ShoesCheaney Deal Burnished Pebble-grain Leather Derby Shoes
  • Lanvin Elasticated Leather Derby ShoesLanvin Elasticated Leather Derby Shoes
  • Churchs Northwood Split Toe DerbyChurchs Northwood Split Toe Derby
  • Kg Kurt Geiger Atherton Leather Derby ShoesKg Kurt Geiger Atherton Leather Derby Shoes
  • Reiss Anderson Grained Leather Derby ShoesReiss Anderson Grained Leather Derby Shoes
  • Aldo Galerrang Leather Derby ShoesAldo Galerrang Leather Derby Shoes

Penny Loafers

Don’t box up your penny loafers just yet. They were big on the Gucci catwalk and, right now, what Gucci says goes. “You may need a pair of socks though,” says Goldup. Well, unless you can stretch to the brand’s fur-lined versions.

You need to be ballsy to pull off the loafers-with-socks trend, though. To stay true to the Gucci look, wear with bunched-up hiking socks and either turn your jeans up or tuck them in. Think of it as cyclist chic. It’s a punchy move that deserves a statement shoe; try embellished or tartan loafers and make sure you buy a half size up, so they fit all that wool.

You can still wear simpler designs when the nights draw in, but make sure they’ve got more heft where it matters. “Choose a style with a chunkier sole as they’ll be more versatile,” says Katner. A thick rubber or plastic sole will help fend off the weather and give you grip. Just avoid too much other embellishment and keep your socks the same colour as your trousers.

Men's Penny Loafers Outfit Inspiration Lookbook - Autumn/Winter 2016 Shoe Trends

faconnable 2015mango man AW16aquascutum ss15mango man 2016

Key Pieces

  • John Lobb Lopez Leather Penny LoafersJohn Lobb Lopez Leather Penny Loafers
  • Tods Polished-leather Penny LoafersTods Polished-leather Penny Loafers
  • Edward Green Duke Leather Penny LoafersEdward Green Duke Leather Penny Loafers
  • John Lewis Lloyd Penny LoafersJohn Lewis Lloyd Penny Loafers
  • Grenson Ashley Penny LoaferGrenson Ashley Penny Loafer
  • Common Projects Crepe Penny LoafersCommon Projects Crepe Penny Loafers
  • Walk London Henley Crepe Sole Penny LoaferWalk London Henley Crepe Sole Penny Loafer