Transition season lasts far longer than September these days, so it’s helpful to think in layers depending on the weather. Here are some classic pieces with a fresh twist to take you straight into winter.

1. Black Merino Wool Turtleneck: With jeans or a pencil skirt, this is always a chic option. $55

2. Denim Straight Midi Skirt: a nostalgic 70’s essential. $129

3. Navy Stripe Silk Shirt: A silk shirt can go from tailored to sexy. $198

4. J. Crew Black Stretch Pencil Skirt: Pencil skirts look good on most figure types and we’re glad they’re back with a vengeance. $89.50

5. Skip the blazer and go for a bomber: this one you can dress up or down in heavy crepe. $248

6. Cashmere Oversized Double Zip Cardigan in beige: We’ve all got enough grandfather cardigans in our closets, This is a hipper version. $378

7. Madewell Ballet Flat: Ballet flats are the shoe of the season, and this one has a comfy, stretchy strap and comes in classic and fun colors (Silver! Turq suede!) at a good price. $98

8. Dark Denim Stovepipe Jean: Baggy denim isn’t going anywhere; this one is a bit dressier in dark denim. $128

9. White Poplin shirt with exaggerated collar and cuffs: If you’re on the hunt for a new white shirt, this one isn’t basic. $80

10. Slouchy Ankle Boot: a classic block heel, updated with a slouch. $269.95

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