1. Oversized Cardigan: I spend the entire year looking forward to these few months of fall. As much as I love coats, it's liberating to wear a sweater as outerwear. Fall is about wearing layers without feeling like you're encumbered by them (hello New England winters!). I usually pair an oversized cardigan with a plaid Steven Alan shirt and skinny jeans tucked into knee-high boots. But this season I'm going to try wearing more skirts and short dresses. (Lutz & Patmos Cardigan $495)
2. Short (Wool) Skirt: Every September I search for a short skirt, preferably wool, to wear while bicycling. Since I don't have a step-through frame, it's absolutely important that the skirt isn't too restricting or flips up in the wind. I keep vacillating between a gathered school-girl silhouette and something more structured and vaguely tulip shaped. My ideal skirt needs to be able to work for both school and going out with friends. This Jcrew skirt would pair really well with a boat-neck striped cashmere sweater. Along with the plaid shirt+denim combo, this is my fail-safe outfit. (JCrew Shirred Wool Skirt $78)
3. Ankle Boots: I was on the fence about ankle boots for a few years, mainly because I wasn't convinced that they would look good on my non-spindly legs. However, I have decided to take the plunge this fall. Winter means that I cover every square inch of my body with something woolen. Knee-high boots are usually paired with wool tights, wool socks, and wool thigh-high legwarmers. The end result is sometimes less than pretty. I thought it would be nice to try wearing a short skirt/dress with tights and ankle boots for the brief time that the temperatures allow. (Dieppa Restrepo Lupe Desert Boot $265)
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