1. Step out of your outfit’s comfort zone

Wear a surprisingly structured dress to lunch instead of your regular tee-and-jeans getup. Add pumps and a cardigan, and you might find that your party dress and Sunday-best shoes look even cuter in a new and unusual environment.  How presh!

In Good Taste Ivory Satin Dress, $38, lulus.com

2. Embrace the turtleneck!

Think of a slouchy turtleneck as a comfy, cute, and super chic all-in-one alternative to a sweater and scarf. Layer it over a skirt, skinnies, or printed leggings.

Sparkle & Fade Slouchy Turtleneck Sweater, $40, urbanoutfitters.com

3. Time travel

Amp up classic looks with retro twists, like this sheath dress. The curve-hugging fit and peplum accent are trendy and modern, but the cap sleeves and candy apple hue simply scream “Old Hollywood.”

Sheath’s Got The Look Dress,  $50, modcloth.com

4. Stay pretty (and cozy!) in pastel

Transition smoothly with outerwear that will carry you from the coldest days of winter all the way through to spring. Try a long coat in a spring-y pastel color, or a shorter one with a removable fur collar.

Mossimo® Women’s Collarless Coat, $42, target.com

5. Hats on!

Kick your ponytail rut and weatherproof your accessorizing habits with a warm, cozy, funky-meets-fancy wool hat. Pair it with your going-out dress, or use it to polish up your casual garb. (Psst…This one is a steal at under $20!)