In winter when it’s cold if you want to wear skirts and dresses wear knee-high boot with opaque tights. Philadelphia Phillies fighting hot dog la vista Baby Philly Phanatic shirt You can now even get fleece-lined thermal tights that keep your legs warm if it’s super cold where you live, otherwise, just opt for regular opaque tights (70 deniers are good and they are hardy as well). Blend the colour of your tights to the colour of your footwear for more elongation. If you want to wear an ankle boot with your skirts and dresses, remember this is leg-shortening, so make sure you match your hosiery to the colour of the boot to create a longer line of the same colour rather than cutting yourself off at the ankles. If you’re wearing skinny jeans or leggings, then knee-high boots are also great as they fit snugly over the jeans, you can also opt for ankle boots too with this style of jeans. Blending the colour of your ankle boot to your trousers or jeans makes your legs look longer and is always a good option. Go for an ankle boot (that’s why bootcut are called bootcut) – because you wear your boot underneath the jean – I’m thinking it was a cowboy boot originally, but any shorter boot style will work. Wider more voluminous trousers need a more substantial shoe for balance. These work best with trousers unless you have very long legs or are wearing a short skirt (above the knee). You can wear oxford or lace-up styles with socks, make them an attractive sock, or even a fishnet sock works well with them under a pair of trousers. Wide-leg trousers work well with a more substantial shoe, from platform wedges to flatforms (these are flat versions of a wedge, they don’t have a raised heel but they have a platform sole) as the scale of the wide leg and scale of the sole balance each other out. Rather than your typical running shoe or sports sneaker, fashion sneakers from Converse or Vans to other more refined styles also work with your jeans and even knee-length skirts and dresses – they should be worn with a no-show sock if you can see your ankles, so are better for warmer weather rather than the depths of winter.

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Corduroy pants may have fallen from mainstream popularity, but they have remained the dandy’s winter legwear of choice. Philadelphia Phillies fighting hot dog la vista Baby Philly Phanatic shirt They’re comfortable and casual yet somewhat smart, which puts them in a unique position whereby they can look equally at home with sneakers and a T-shirt or casual tailoring. The degree of stretch provided by the cord fabric makes them more akin to sweatpants than jeans on the comfort spectrum, and the thickness of the wales (that’s the name for the raised fuzzy strips) does an excellent job of insulating against the cold. We think they look great with an unstructured blazer in a complimentary colour, a pair of loafers and a classic wool overcoat. Your average chinos simply aren’t going to cut it when the weather is at its coldest. Of course, that’s not to say you should stop wearing chinos entirely during the winter. After all, we’re talking about one of the most versatile and classic legwear options there is – it would be a shame to simply cast them aside for the entire season. That’s why heavyweight twill chinos, with their thicker fabric, are our go-to smart-casual trousers during the colder portion of the year. Wear them with an Oxford shirt, knitted sweater, desert boots and a parka for a foolproof smart-casual winter look. For cosy days around the house, nothing does it like a proper pair of heavyweight sweatpants. These aren’t your average high-street joggers – they’re ones made from super warm fleece-backed jersey cotton that’s thick, soft and perfect for keeping warm. We love these things because they’re surprisingly versatile if you’re bold enough to get a bit creative with your styling. Granted, you probably aren’t going to be wearing them to a black-tie dinner, but do they always have to be paired with a slouchy hoodie and a pair of sneakers? Absolutely not. Try throwing on some knitwear, an overcoat and a pair of comfortable casual shoes like a pair of Clarks Wallabees to give these laid-back pants a completely different feel.