Here's how to style baggy jeans for autumn 2026

The older I get, the more I appreciate a really good pair of baggy jeans. They’re the fashion equivalent of cancelling plans: comfortable, easy to wear and almost always the right decision. Styles vary between sitting high on the waist or grazing the hips, but whichever waistband you go for, baggy jeans typically have a loose, slouchy leg that makes even the most basic outfit feel considerably cooler. Either way, I’ve become increasingly devoted to denim with a wonderfully slouchy silhouette. But what shoes do you pair with them?

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Unlike skinny jeans, which demand a certain amount of commitment, or barrel legs, which can occasionally feel like you’re cosplaying a cowboy, baggy denim is refreshingly unfussy. The best pairs flatter the body, puddle slightly over your shoes and bring a relaxed, borrowed-from-the-boys quality to everything from a white T-shirt to a sharply tailored blazer.

The secret to nailing the baggy denim trend lies in the footwear. You want something that contrasts, adds structure or a touch of sophistication, to balance out the slouchy silhouette of the jeans – think well-chosen heels, a pointed toe, an interesting fabric or a high-shine finish.

Of course, autumn and winter present a rather different styling challenge to summer. Those barely-there sandals and dainty flats that worked so beautifully with oversized denim in July are suddenly less appealing when the pavements are wet and the temperature has dropped into single digits. And anyone who’s spent an afternoon dragging several inches of denim through London puddles will know that the wrong shoes can quickly ruin a perfectly good outfit.

Trainers make them feel sporty, ballet flats add an unexpected delicacy and pointed heeled boots turn all that extra fabric into something far more glamorous. Consider this your guide to finding the perfect pair.

We’ve narrowed down the outfit formula of the moment into seven essential styles, so you’ll never wonder what shoes to pair with baggy jeans ever again.

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