1. Top It Off
A beanie may very well be your best friend come winter. Wear it slightly back on your head, like Danielle Bernstein of We Wore What, so your pretty face isn’t hidden.
2. Schoolgirl Staple
Leave it to Blair Eadie of Atlantic-Pacific to make the preppy mainstay—over-the-knee socks—look utterly stylish. We love them as an alluring alternative to tights.
3. Color Theory
Everybody owns a black coat, so why not stand out with an unexpected outerwear color? According to the most stylish civilians, including Victoria Tornegren of Victoria Tornegren, the color of the moment is pink.
4. Sock It To Me
If it’s still warm enough to sport a bare leg, add socks to your favorite pair of oxfords for a little extra warmth like Christina Caradona of Trop Rouge.
5. A Slip Of Lace
We’re totally copying Andy Torres of Style Scrapbook’s peek-a-boo lace under a chunky turtleneck look for our next winter date night.
6. Layering Trifecta
This fail-proof combination of a button-down, sweater, and coat as seen on Anna Jane of See Jane is ideal for a professional work outfit.
7. Statement Scarf
If your outfit seems a little lackluster, the easiest way to add interest is with a chunky scarf. Extra points for a pattern, like Shini Park of Park & Cube’s hounds tooth print.
8. Double Trouble
The old J.Crew styling trick of doubling up your button-downs looks especially fresh with two shades of denim. Add some edge to the preppy look by pairing your collared shirts with a pair of leather trousers, like Daniella Robins of Lella Victoria.
9. Layering With Edge
Prefer a tougher look? Just take the previously mentioned layering trifecta and replace the sweater with a moto jacket. We also love the addition of a chunky beanie like Sara Strand’s of Sara Strand.
10. Turtleneck + Oversized Sweatshirt
By the sound of it, this combination may seem like a recipe for dowdiness. Yet as Camille Charrière of Camille Over The Rainbow shows, when paired with a miniskirt and over-the-knee boots, the effect is cozy and chic.
11. Boots As Leggings
We always look to Irina Lakicevic of A Portable Package for creative outfit ideas. Her solution to wearing a mini skirt in winter? Just pair it with a tall pair of over-the-knee boots.
12. Sweater Weather
Sometimes a thick sweater can be just as cozy as a coat. Take note from Chiara Ferragni of The Blonde Salad and pair a bohemian-inspired knit with skinny jeans.
Choies Deep Gray Longline Wool Coat ($81)
Club Monaco Luella Cashmere Scarf ($160)
Wigwam Cypress Socks ($12) in Navy
Adrienne Landau Rex Scarf ($450)
Jeffrey Campbell Backside Over The Knee Boots ($280)
Warehouse Borg Biker Blazer ($134)
Tory Burch Moser Glove ($165) in Dark Plum
Jonathan Simkhai Color-Block Jersey Sweater ($315)
Zara Dotted Tights ($17)
H&M Angora-Blend Hat ($30)