The sting of summer's end is real -- and best soothed with a hefty serving of fall fashion. And what else brings instant joy more than a new purse? Talking specifics, our fall wardrobes always have a hankering for a buttery, caramel leather style, which is why Rachel Zoe hand picked JJ Winter's petite crossbody style for the newest edition of Box of Style. From its magnetic top-flap closure, to its gleaming hardware and adaptable strap, is everything we're excited to wear with chunky knits, lightweight jackets and endless pairs of boots. Below, we showcase how to style a crossbody bag with summer-to-fall versatility.

Weekend Errands: With An Army Shirt And Fitted Denim

Military-inspired styles are big again for fall, and look stunning when paired with caramels, tans and browns. Sling your bag across your body and complete your ensemble with a mid-wash blue jean and classic sneakers. 

Dinner With Friends: A Midi Dress And Leather Mules 

The petite size of this bag is perfect for an evening out. Lengthen the strap and wear it on one shoulder for a hit of effortless polish, and as temps drop, top with a black leather jacket. 

Coffee Meeting: With A Cardigan Coat And Nude Boots

For days you want to feel comfortable but still need to look polished, pair your crossbody bag with a stacked heel boot, printed skirt and a nubby knit sweater. Top the entire ensemble with a cardigan or robe coat.