Consider it the B side to the American dream—instead of the white picket fence and the well-manicured lawn, there are those whose fantasy involves sweeping expanses of wild terrain, no neighbors in sight and a general willingness to do things the hard way.
For those of you looking at the new shapes of denim—wider legs, frayed edges and cropped hems—and wondering which boots to wear with ’em, we’ve got you. Or rather, our stylist Pippa does. Here, she breaks down the wardrobe recipes you need now. Get a leg up. A step in the right direction. Let’s get kicking. (You get the idea.)
Snapping a “perfectly laid-back, styled but not too” shoe shot does take a little bit of work, but it’s never been more worth it. Post yours for a chance to win a $2,000 Madewell shopping spree plus everything you need for a perfect day of strolling: two pairs of Madewell boots (your choice), Grado headphones, one year of Spotify Premium, a Mizu water bottle and snacks from Baked.* Now, to make sure you nail those photos, we gathered up five tried-and-true tips. Let’s get snapping.