1. THE WEATHER-READY PAIR
Winter’s on its way, and with it, the issue of winter footwear. Last year, my superb but oh-so-sensible snow boots were worn ad nauseam, so this year, I’m bringing these shearling-lined Frye moto boots into the rotation. Goodbye, boot boredom!
2. KNEE-HIGH CLASSICS
This is the pair you’ll be able to wear with everything this fall. There’s nothing more seasonally appropriate than a classic knee-high boot with skinnies or a skirt and a cozy sweater, like these Tory Burch knee-high boots. So easy.
3. ANKLE BOOTS
I love a classic leather ankle boot, like these Rag & Bone booties. Their versatility transcends new seasons and trends. Skirts, slouchy pants, sweater dresses—everything looks smarter with ankle boots. Extra points for slip-on styles! Nothing like slipping them on and leaving the house feeling and looking awesome.
4. OVER-THE-KNEE BOOTS
Once the weather gets cool, pointy pumps belong at the back of the closet—nobody should have to wear heels in the cold! That’s why over-the-knee boots, like these from Stuart Weitzman, are a nice investment to make around this time of year. They’re as chic and sexy as a pump—but they’ll keep you toasty on wintry nights out.
5. HIKING BOOTS
Autumn calls for plaids and leather, and normally those grunge elements have me craving combat boots. But this year, it’s all about hiking—or at least, the hiking boot. Unassuming, utilitarian, and kind of badass, a pair of leather hiking boots will add an edgy nonchalance to the most basic autumn look. The laces on these Joie hiker boots don’t hurt, either.