Trailside

For a Saturday spent relaxing and window shopping in Woodstock, Vermont, I needed a casual, comfortable look. To keep it interesting, I layered a graphic tee over a plaid button-down in coordinating colors and topped that with a military-style jacket.

• Jacket (old) Madewell
• Bar Stripe Tee J.Crew
• Classic Button-Down in Gingham J.Crew Factory
• Toothpick Jean in Distressed Cone Denim J.Crew
• Viv Patent Flats J.Crew

Fine Print

For a fun, fall look, I channeled the print mixing genius of Peter Pilotto, Erdem and Mary Katrantzou. Miraculously, I got all the colors in both prints to match up, making it super easy to pull patterns together.

Since the weather at this time of year is pretty unpredictable, I layered a denim jacket over a blue blazer – both of which added texture and balanced out the formality of the look. I finished the look with blue shoes to create a cohesive color palette.

• Printed Scoopneck Blouse in Green Foulard J.Crew Factory
• Boy's Trucker Jacket Levi's
• Blazer (old) Benetton
• Café Capri in Bazaar Print J.Crew Collection
• Valentina Patent Pumps in Deep Violet J.Crew

Blue Period

Whenever I’m faced with an unseasonably temperate day, I’m also faced with the subsequent panic attack about what to wear.

Instead of dumping the entire contents of my closet onto my bed, I made the simplest outfit I could think of, using the the minimum number of pieces that could comprise an outfit. I stuck to one color and a loose top, skinny jeans silhouette and got on with my day.

• Linen Baseball Sweater J.Crew
• Skinny Skinny Ankle Jeans Madewell
• Valentina Pumps in Deep Violet J.Crew