The Best Ann Taylor Sweaters for Winter

Four Must-Have Styles
Jennifer Lake Blue Floral Mural
Sweater: Ann Taylor Chevron Raglan Sleeve Sweater | Pants: Ann Taylor Sculpting Pocket Mid Rise Tapered Jeans | Shoes: Ann Taylor Kiltie Suede Flats | Jewelry: Ann Taylor Hoop Earrings | Bag: Mark Cross Grace Bag | Eyewear: Illesteva

How was your Christmas and Hanukkah, friends? It was absolutely FREEZING in Chicago; that arctic blast was no joke. Thankfully, I’ve stocked up on the best Ann Taylor sweaters that are making winter more cozy, comfy and stylish. They are the ideal layering pieces to stay warm in this frigid temps.

Ann Taylor Sweaters

Moreover, Ann Taylor is one of my fave go-to brands for workwear. As most of you know, I work full-time and go into an office. Therefore, sweatpants and loungewear are no longer on a regular rotation for my wardrobe. Instead, I’m constantly dressing up or finding casual pieces to still look presentable for meetings and general work days.


Mark Cross Grace Bag

Over the past year, my closet has developed a healthy amount of sweater styles from the brand. One thing that Ann does better than any other brand is offering complementary pieces throughout their seasonal collections. The blues match other blues, lilacs pair well with other lilacs… you get the piciture.

Ann Taylor Tan Suede Fringe Flats

Frankly, this makes mixing and matching items easier than ever. I never have to worry about finding chic color combos or matching items (and I LOVE anything matchy matchy, lol). Plus, I’ve developed a strong affinity for monochromatic looks at the office. A matching top and trousers? So good. Monochromatic looks just give off that effortless, easy vibe.

The Best Ann Taylor Sweaters for Winter

Ann Taylor Raglan Sleeve Sweater

So which sweater should you start with? The Ann Taylor Chevron Raglan Sleeve Sweater. Friends, it’s SO good. Love the bright blue and white combination, and the sweater is SO soft. Plus, the Ann Taylor sweater is super versatile. I styled it with mid rise white jeans, but you can also wear it with denim, faux leather pants, and a sweater skirt. So chic!

Ann Taylor Blue Tan Coat
Dress: Ann Taylor Stripe Belted Shirtdress | Sweater: Ann Taylor: Striped Trim Cascade Cardigan | Shoes: Ann Taylor Azra Suede Pumps | Scarf: Ann Taylor Floral Silk Little Scarf | Jewelry: Ann Taylor Hoop Earrings | Bag: Chloé | Eyewear: Amazon

Ann Taylor Striped Cascade Cardigan

Next up is this stellar striped cardigan. I love layering it over this Ann Taylor Stripe Belted Shirtdress and Azra Suede Pumps. Navy dresses are always a great option for work attire (I have a whole philosophy on color theory at work, but I’ll leave that for another day).


Ann Taylor Trimmed Cardigan

Additionally, I added this stylish scarf to an old designer bag. In general, I’ve been loving scarves this year, and excited to find new ways to style this piece next year.

Ann Taylor Stripe Shirt Dress

Ann Taylor Stripe Mixed Stich Sweater

Would it be a Style Charade winter fashion post if there wasn’t a multi-color striped sweater? Wow, I love this piece. First, the sweater is the perfect length – not too short, not too long, just right. I’m a big fan. Plus, the colors are classic yet fun. It’s the ideal sweater for those of you who don’t want something TOO colorful. But color lovers also get a healthy dose of haute hues.

Ann Taylor Stripe Mixed Stick Sweater
Sweater: Ann Taylor Stripe Mixed Stich Sweater | Pants: Ann Taylor The High Waist Slim Pant | Jewelry: Ann Taylor Hoop Earrings | Bag: Mark Cross Grace Bag | Shoes: Manolo Blahnik BB Pumps | Eyewear: Celine

For work wear, I styled the Ann Taylor stripe sweater with these high waist slim pants. But for more casual occasions, I’ll style it with jeans or leather leggings. I find the pants to fit true to size, and the length is fabulous (showing off your shoes and not too long). Keep in mind, I’m 5’4 on a good day. Thankfully, Ann Taylor offers both petite and regular sizes (I’m wearing petite).


Mark Cross Box Bag
Also, don’t sleep on this set of hoop earrings set from Ann Taylor.

The set comes with so many different weights of gold hoops, so there’s literally a style for all occasions.

Ann Taylor Stripe Sweater

Last but not least, I decided to pair it with a Mark Cross Grace bag. It’s one of my absolute favorite bags of all time. The silhouette and structure is so clean and classic. Mark Cross has easily become one of my fave designer brands to invest in, and I will truly have this bag in my wardrobe forever.

Ann Taylor Tan Orange Stripe Sweater
Ann Taylor Navy Turtleneck
Turtleneck: Ann Taylor Shoulder Button Mock Top | Shirt: Ann Taylor Chambray Relaxed Perfect Shirt | Pants: Ann Taylor Sculpting Pocket Mid Rise Tapered Jeans | Sweater: Ann Taylor: Striped Trim Cascade Cardigan | Shoes: Ann Taylor Azra Suede Pumps | Jewelry: Ann Taylor Hoop Earrings | Bag: Chloé | Eyewear: Illesteva

Ann Taylor Shoulder Button Mock Top

In addition to the dress and cardigan combination, I wanted to share a second way to style the navy stripe trim cardigan. I love this more casual layered look with several Ann Taylor pieces. My office gets VERY cold during the winter, so I’m grateful this outfit has three layers to keep me warm.


Ann Taylor Navy Tan Trimmed Cardigan

Start with the Ann Taylor Shoulder Button Mock Top mixed with this chambray button down shirt. You may already even have pieces like this in your closet. However, if you’re looking for stylish staple tops, this shoulder button top is a winner. It does run a bit large, so I’d recommend sizing down one size.

Navy Suede Chloe Bag
Ann Taylor Navy Long Cardigan
Chloe Pixie Bag
Ann Taylor Preppy Layered Look

What are some of your Ann Taylor sweaters lately? Drop a comment below and let me know some of your favorites. I’d love to hear what pieces are catching your eye from the collection. Lastly, I’ve round up some of my personal faves from their collection lately below. Happy shopping!

Sweater: Ann Taylor Chevron Raglan Sleeve Sweater | Pants: Ann Taylor Sculpting Pocket Mid Rise Tapered Jeans | Shoes: Ann Taylor Kiltie Suede Flats | Jewelry: Ann Taylor Hoop Earrings | Bag: Mark Cross Grace Bag | Eyewear: Illesteva

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