10 Ann Taylor Winter Fashion Deals from $20

Without fail, the gaps in my wardrobe tend to reveal themselves right after Christmas each year. Thankfully, that means I can use my gift money to snag must-have winter fashion while so many brands are running major sales. 

This year, I’m completing my cold-weather wardrobe with pieces from Ann Taylor, while on-sale styles are marked down an additional 60 percent off through January 11. The semi-annual sale includes so many elegant staples, such as mock-neck cardigans, jackets with unique embellishments, and comfortable pants that look super polished — all starting at just $20. Shop my picks for up to 69 percent off below, before they sell out.

Editor-Approved Fashion Picks at Ann Taylor’s Semi-Annual Sale

• Unique Design: Embellished Herringbone Cropped Jacket, $64 (orig. $198)
• Collared Double Face Jacket, $76 (orig. $209)
• Shimmer Crew Neck Cardigan, $50 (orig. $159)
• Winter-Ready Colors: Ribbed Turtleneck Sweater, $30–$55 (orig. $95) 
• Mock-Neck Cardigan, $30 (orig. $98)
• Weekend Collection Waffle Sweater Pant, $38–$79 (orig. $109)
• Sellout Risk: Weekend Collection Quilted Vest, $58 (orig. $159)
• The Pleated Wide-Leg Pant, $50 (orig. $149)
• Layering Must-Have: Weekend Collection Ruffle Mock-Neck Top, $20 (orig. $60) 
• The Margot Pant, $40–$44 (orig. $129)

Weekend Collection Waffle Sweater Pant

My secret to feeling comfortable while looking put together is a pair of relaxed yet polished pants that can be worn with just about anything. The waffle sweater material on this pair fits my criteria, and can be styled with a matching sweater, blouse, or casual sweatshirt for various occasions. I’m eyeing the navy blue shade, but I might also snag them in plum while prices start at just $38. 

Embellished Herringbone Cropped Jacket

A staple wardrobe piece doesn’t have to be boring — this cropped jacket with an embellished neckline will be a go-to in my winter wardrobe when I want to quickly dress up jeans and a T-shirt. The black and white herringbone design is classic, and one shopper who called the piece “super versatile” added that the “shell-like structure” is still flexible.

Ribbed Turtleneck Sweater

I rely on layering during colder months to combat fluctuating temperatures in Los Angeles. This ribbed turtleneck sweater is a timeless top I can wear solo or under a jacket. One shopper who said it is ideal for “cool days” also shared that it’s “cute layered with a denim jacket.” The versatile sweater is currently on sale in three winter-ready colors, including red, green, and plum. 

Weekend Collection Quilted Vest

On sunny days when there is still a chill in the air, I love reaching for a vest to keep warm without overheating. This puffer style has gold buttons to give it a dressier look, and I love how the crew neckline looks when layered over a sweater or blouse. This piece is available in white and navy blue in both standard and petite sizes, and I’m adding it to my cart ASAP before more sizes sell out. 

Keep scrolling to shop more winter fashion staples I’m eyeing while they’re on sale at Ann Taylor. 

Weekend Collection Ruffle Mock-Neck Top

The Margot Pant

Mock-Neck Cardigan