What Shoes To Wear With Baggy Jeans According To A Fashion Editor

Deciding what shoes to wear with baggy jeans is arguably the only difficult thing about them. Baggy jeans are the fashion equivalent of cancelling plans: comfortable, satisfying 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.

Featured in this article:

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.

It is hardly surprising, then, that street stylers have continued to favour exaggerated, floor-skimming jeans over more restrictive denim shapes. The appeal is not simply that they are comfortable – although that certainly helps – but that they can shift personality entirely depending on what is happening below the ankle.

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.

Trainers make them feel sporty, ballet flats add an unexpected delicacy and pointed heels 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 nine essential styles, so you’ll never wonder what shoes to pair with baggy jeans ever again.

Skip to: