Ever since Kendrick Lamar performed at the 2025 Super Bowl, the streets are clamoring for flared jeans, the Y2K classic that's ... shrug paired with matching black flare jeans.

Since this bottom style is so baggy ... what shoes to wear with denim, let Y2K outfits serve as a source of inspiration. Pair flare jeans with sleek black boots and opt for a small kitten heel ...

The last thing you want is for your flare jeans to drag on the ground. Here are the best shoe styles for keeping your hem high and style fresh.