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What goes with what

Four go-to footwear pairings

Four go-to footwear pairings

Like bread and butter, fish and chips, or bangers and mash, some things are just better together. And that’s as true about the stuff in your wardrobe as the stuff on your plate.

Grounded as it is in a history of uniforms (both literal and metaphorical), the staples of what men wear – suits, chinos, shirts, overcoats – would still be recognisable to the men who first wore them more than a century ago. Which proves just how long a truly great pairing lasts.

Shoes are no different. Generally, they’re more versatile than everything else in your wardrobe – a great pair of brogues works with everything from chinos to jeans to suit trousers – but there’s always a piece that feels so right, it’s like they were made for each other. Once you know what to pair with what, picking the right pieces becomes much easier.

Think of it like this: you know to order white wine with fish and red wine with steak. That narrows down the wine list and lets you focus on which bottle is best. This isn’t so different. Once you know which categories go together, you need only worry about the specifics – fit, colour, patterns – to create combinations that are more than the sum of their parts. To get you on your way, we’ve tapped Thread stylist Freddie Kemp to share a few of his go-tos, and show you where to start when stocking your own wardrobe.

Loafers + polo shirts

Why it works: The cornerstones of a preppy uniform, worn by everyone from JFK to Dickie Greenleaf, look as good today as they did in the 1950s.  “It’s a summer or holiday combination that always works,” says Freddie. “They’re quite smart shoes, so can sometimes feel too jarring with a t-shirt, but neither do you want to be wearing long-sleeved shirts when it’s hot.”

Stylist tip: “Look for good quality leather,” says Freddie. “And bear in mind that you might have to break them in a bit before they’re really comfy.” Try penny loafers as opposed to tassel loafers – they’re easier to wear and less fussy. For the polo, pick colours that you wouldn’t normally buy shirts in. There’s more room for experimentation, so embrace it. “Go for some bolder seasonal colours, which the piqué cotton can carry off.”

Brogues + Oxford shirts

Why it works: “This might not be the most glamorous combination, but it really is tried and tested,” says Freddie. “They’re always going to be staples in menswear, which means you can invest in confidence that you’ll get so much wear out of them.”

Stylist tip: When even Goldman Sachs are letting their employees go without a tie, a button-down shirt is going to get worn more often than anything with a starched collar. So go for a brand that specialises, like Gant, Ralph Lauren or United Colors of Benetton. “They are classic brands that have been doing this for so long that they’ve basically perfected the art of the button-down shirt.”

Trainers + sweatshirts

Photographed: Polo Ralph Lauren Bear Crew Sweat ($172)

Why it works: It’s simple, but get this combo wrong and you just look like it’s laundry day. As Freddie notes, there’s a very relaxed, sporty, weekend feel to this combination. He adds: “Throw it on over jeans or a pair of tapered joggers for that off-duty feel.”

Stylist tip: Trainers and sweatshirts have their roots in gym kit, and comfort still matters. “If you’re active, these are designed for you,” says Freddie. But neither should look like the kit you actually wear to the gym. Rather than going for a plain sweatshirt, try one with a graphic on the front to make more of a statement. That frees you to experiment with colourful, running-style trainers rather than anything white and minimalist.

Canvas trainers + light-wash jeans

Why it works: Dark-wash jeans have become the ‘safe’ option in recent years, but for casual summer days, there’s nothing like a pair of light-wash jeans. “There’s something about the shape and the colour of the jeans that give them a retro style,” says Freddie. Double-down on the nostalgia with canvas trainers inspired by the original basketball shoes.

Stylist tip: Beginning life in 1949, the Pro Keds Royal Hi Trainers are an alternative to the ever-popular Converse, with as much history but less chance of seeing someone else wearing them. “There’s that great element of rock and roll to them,” says Freddie. It’s old-school style that’s still perfect for right now.

Words: Theresa Harold
Photography: Chris Howlett
Styling: Freddie Kemp and Luke McDonald