A simple jean + shoe pairing guide The secret isn’t necessarily matching the shoe to the jean—it’s making sure the shoe shape, height and jean hem work together. Straight-leg jeans pair beautifully with refined loafers, pointed or almond-toe flats and sleek ankle boots. With wide-leg denim, I look for a shoe that has enough presence beneath the wider hem, while cropped denim usually looks more polished when the boot shaft minimizes that awkward ankle gap. Pro tip: If the shoe looks wrong, check the jean length before replacing the shoe. Sometimes the hem is what’s throwing off the proportion. I’m linking similar loafers, flats, ankle boots and denim styles so you can recreate these pairings for fall. LTKStyleTip LTKShoeCrush DenimStyle JeanStyling FallShoes FallFashion Over40Style ClassicStyle LTKOver40 LTKOver40