1. Do like Charlotte Di Calypso and wake up your favorite basics like a tailored black blazer and skinny jeans with an elegantly patterned silk scarf. Enlarge Image
Above, from left: Madewell Leggings Jeans, $95, available at Madewell; Ralph Lauren Turquoise Mocassins Scarf, $220, available at Stylebop; Marc by Marc Jacobs Helena Convertible Tote, $458, available at Saks Fifth Avenue; Chelsea Crew Classic Oxfords, $58, available at Urban Outfitters.
2. Follow Alana Zimmer's lead and give your tough-girl leather jacket a ladylike spin with a floral dress and a structured satchel. Enlarge Image
Above, from left: Coach Tyler Leather Moto Jacket, $698, available at Coach; Dolce Vita Mica Dress, $198, available at Urban Outfitters; Proenza Schouler Large Suede PS1 Bag, $1,995, available at Barneys New York.
3. Copy Karlie Kloss and use a statement coat and gorgeous bag as the focus for a truly simple daytime outfit. Enlarge Image
Above, from left: BCBG Essential Knit Turtleneck Dress, $68, available at BCBG; Clinique High Impact Lip Colour in Red-Y To Wear, $14, available at Nordstrom; Karen Millen Cape, $379.13, available at ASOS; Big Buddha Empire Bag, $86, available at Lori's Shoes.
4. Get inspired by Lindsey Wixson and skip the matchy-match and mix navy, gray, and black to get a more personalized and textured take on a classic fall look. Enlarge Image
Above, from left: Marc By Marc Jacobs Normany Pullover, $250, available at Stylebop; Daftbird Side Pleats Skirt, $50, available at Revolve Clothing; HerCut The Ponytail Styling Lotion, $22, available at Sephora; American Apparel Round Collar Button-Up, $46, available at American Apparel; Nine West Boutique 9 Cooper Boots, $169, available at Nine West.