5 Shoe Mistakes You Could Be Making

And how to fix them

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There's something very easy about dressing for the summer month, the effortlessness of simply throwing on a shirt and being ready to leave the house is very seductive indeed.

The same applies to footwear. In the warmer months you don't need to think about socks, for instance. Pull on a pair of trainers, espadrilles, sandals, sneakers or loafers and you're good to go. So long as the hems of your trousers don't fall too low, it's incredibly easy to look smart from the waist down when it's warm.

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Come winter, there's a whole new host of problems to contend with – issues you'd all but banished from your mind during the halcyon days and balmy nights of summer.

Is it better to wear boots or brogues, for instance? And which is more suitable for work? What do you do with cropped trousers? And how does one navigate the sartorial minefield of a turn-up? Here, to help you get your head around the manifold potential pitfalls, is our guide to wearing winter footwear.

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1 | Embrace a bold sock

When it comes to wearing any type of low-top shoe, the likelihood is you're going to struggle to get your trousers to the right length. If they're too long, they'll puddle and drown the shoe – too short and you'll just look silly. The best thing to do is to opt for a tapered trouser with a slight crop.

If you're wearing sneakers or casual shoes (such as desert boots) opt for a bright, block colour sock in something like yellow or purple. If you're wearing smarter shoes stick with a tonal shade (navy trousers = slightly paler or darker blue socks). This way you'll make a feature out of the potentially awkward gap between trouser and shoe – pretending it doesn't exist will only make it worse.


Highland heather socks by The London Sock Co, £12

2 | With boots, wear a turn-up

There is nothing worse than wearing your trousers or jeans over the top of your boots. Just look at David Cameron – who wore his suit with a pair of Chelsea boots back in April – or Rafe Feinns whoo ruined a perfectly lovely tux on Monday night's Bond premier, by wearing it with a pair of chunky boots. When wearing boots always turn up your trousers or jeans to sit just at the top of the boot, and wear a sock in a similar shade. Alternatively, if you're going for a smarter look, get your trousers taken up and tapered in so that they kiss the top of the boot.


Turn up gabardine trousers from Gucci, £400

Black leather chelsea boots from Russell & Bromley, £185

3 | When it comes to sneakers, choose a high-top

If you don't fancy wearing a bright sock and a turn up with your sneakers, opt instead for a high top and apply the boot rules, above. A Converse baseball boot (opt for the brand's new, harder wearing Chuck II) teamed with a pair of rolled up jeans, a waffle knit cream jumper and a midnight blue pea coat is a perfect off duty look.


Dylan slim jeans by Adriano Goldschmied, £247

White Chuck Taylor All Star II by Converse, £60 

4 | You can still wear loafers

Car shoes and slippers aside, you can continue wearing your loafers into the winter months. The key here is to wear a cropped trouser with some socks on the same shade and to opt for a loafer in dark black or brown. The best shape is a chunky-soled penny and the best hide is hardwearing cordovan or pebble grain leather.

Pebble grain penny loafers by Tod's, £340

Knee length ribbed cashmere socks in grey by Bresciani, £70

5 | Never tuck in your trousers

In the nineties a number of brands, which shall remain unnamed, perpetuated a lie. It was a lie that encouraged countless men to believe that it was acceptable to ape a pirate and tuck their trousers into their boots. NEVER DO THIS. Herewith, a lovely pair of boots you couldn't tuck your trousers into even if you tried.


Chestnut brogue boot by Crockett & Jones, £460

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