EVELYSS / Guides / Fashion Sense

What Shoes to Wear With Wide-Leg Trousers in Winter (Rain, Office and Evening)

“Wide-leg trousers are rarely defeated by the shoe. They're defeated by the hem, an inch too long and drinking every puddle between the station and your desk. Choose your winter shoe first, then cut the trousers to suit it.”Her take

Which winter shoes work best with wide-leg trousers?

Start with the weather and the setting, not the trend. Wide legs hide most of the shoe, so the part that matters is the toe, the sole and how the hem falls over them.

Tall boots are the shoe to leave out. A knee-high shaft fights the swing of the trouser and creates a bulky line at the shin. If you can see the outline of the boot through the fabric, change one or the other.

• Chunky loafers: the all-round winter choice. The thick sole lifts the hem and the open top looks neat under a full leg.
• Chelsea boots: best for rain. Their slim shaft sits cleanly under the trouser and there are no laces to get wet.
• Pointed ankle boots: smartest for the office, because the point lengthens the leg and the shaft stays out of sight.
• Plain dark leather trainers: best for weekends and long walking days. White trainers look brighter in summer and show winter dirt quickly.
• Block-heeled boots: best for evening, or for full-length trousers that were cut for a heel.

How long should wide-leg trousers be with each shoe?

There's no single correct measurement, but for winter I'd start with a full-length wide leg clearing the ground by about 1 to 2cm at the back while you stand in the shoes you'll actually wear. Wet pavement climbs fabric quickly, so stay at the top of that range. At the front, the hem should rest on the shoe with little or no break.

This is why one pair of trousers rarely works with both a flat and a heel. Take your shoes to the tailor, or pin the hem yourself and walk up and down the stairs before you commit. If you switch between shoes, choose a sole height for each pair of trousers and stick to it.

Cropped wide-leg trousers, ending around the ankle bone, are a different case. They need a boot that closes the gap: an ankle boot whose top sits under the hem, or a loafer with a fine dark sock or opaque tights so no cold skin shows.

How do you stop wide-leg hems getting soaked?

Height is your best protection. A lug or platform sole around 3cm deep raises the whole trouser, so a pair hemmed to clear a flat gains about 3cm of extra clearance. If you're having trousers hemmed specifically for that sole, keep the 1 to 2cm gap at the back and most ordinary rain stops being a problem.

Fabric helps too. Dense wool blends and heavy twill shrug off a splash and dry with their shape intact. Lightweight drapey fabrics stick to the ankle when wet and pull dirt upwards. On a truly foul day, leave the longest pair at home and wear a cropped or straight leg with waterproof boots.

What colour shoes go with winter wide-leg trousers?

Matching the shoe to the trousers makes the longest line. Black with black, navy with navy, or deep brown with chocolate are the easy options. When the trouser and shoe are close in colour, the hem reads as one continuous shape.

For contrast, keep it deliberate. Dark brown loafers look rich with camel, grey or cream trousers, and black boots suit charcoal and most checks. Pale winter trousers are the hardest to wear in town, so give them a darker shoe and a slightly shorter hem.

Five winter outfits to copy

Each of these uses a full or relaxed wide leg and a shoe that can cope with a real British day.

• Office: charcoal wool wide-leg trousers, a fine black roll neck, a long navy coat and pointed black ankle boots.
• Wet commute: navy twill trousers, a cream jumper, a belted trench with a warm layer underneath and dark Chelsea boots on a lug sole.
• Weekend: dark indigo wide-leg trousers, a grey crew-neck knit, a quilted jacket and plain dark leather trainers.
• Dinner: black crepe trousers cut for a heel, a silky camisole under a black cardigan and block-heeled boots.
• Christmas lunch: chocolate brown cords, a cream polo-neck knit and dark brown chunky loafers with fine socks.

What should you do if you can't walk in heels?

You don't need them. Wide-leg trousers often look more current with a flat shoe, provided the hem has been set for that flat. A pointed flat or a slim loafer keeps the look neat, and a slight platform gives you length without a raised heel.

If your trousers are too long for flats, have them taken up. Keep the original hem style if you can, and ask your tailor to leave about 2 to 4cm of spare fabric inside the hem if the trousers allow it, so they can be let down later.

Questions people ask

The takeaway

Choose the winter shoe first, cut the hem for that shoe, clear the ground by a centimetre or two, and let a thicker sole do the rain's work.

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