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If you’re updating your wardrobe—whether you’re returning to the office, refreshing your everyday style, or looking for versatile pieces—Ann Taylor is a reliable option for polished, well-made clothing. While the brand is known for classic workwear, I like to look for pieces that feel less traditionally Ann Taylor—items with unique details, almost boutique-like, that stand out in a thoughtful way.
Right now, Ann Taylor is running its Friends & Family Sale, where you can get 30% off your entire order plus an extra 15% off when you spend $175 or more—making it a great time to grab a few fresh pieces for spring. (Prices below reflect the 30% off.)
For this roundup, I’ve kept reader requests in mind, ensuring a good mix of natural fabrics and wearable styles that balance structure and ease. From refined separates to effortlessly chic staples, here’s what’s worth considering at Ann Taylor right now. Looking for more wardrobe recommendations? Check out my guide to the Best Clothing for Women Over 40.
Best Ann Taylor Pieces for Women Over 40
And as always, I do my best to accommodate everyone—though finding options that work for all body types can be a challenge. Ann Taylor offers both regular and petite sizing, with many styles available in sizes 00–20/22, providing a solid range of options.
Striped Textured Ann Cardigan
Starting strong with this 100% cotton Striped Textured Ann Cardigan, a refined yet versatile layering piece. If your work wardrobe leans on classic black trousers, this is an easy way to add visual interest. I’d wear it buttoned up over a simple cami for a clean, structured look, but you could also style it open over a black tank and matching pants to create a sleek, elongated silhouette.
Striped Textured Ann Cardigan
Ann Taylor
$62.65Available in XXS -XL in classic and petite.
Tropical Collared Midi Flare Dress
Several pieces in this roundup have a major Tuckernuck vibe, including this Tropical Collared Midi Flare Dress. Made from a breathable linen and cotton blend, it’s a perfect choice for spring events—whether you’re attending Easter celebrations, baby or bridal showers, or graduations. The elegant silhouette offers an effortless feel, and you can tailor the hem to your ideal length for a perfect fit.
Tropical Collared Midi Flare Dress
Ann Taylor
$125.30Available in 00 -18 in classic and petite
Weekend Collection Wedge Sweater Vest
Ann Taylor recently introduced a “Weekend” collection, and I’m really loving it. The pieces feel clean, fresh, and thoughtfully styled, offering plenty of inspiration. I would wear this 100% cotton sweater vest as a top and comes in versatile shades of blue, tan, and black. While it pairs beautifully with just about anything, I especially love the idea of styling it with long, wide-leg linen trousers for an effortlessly chic look.
Weekend Collection Wedge Sweater Vest
Ann Taylor
$59.15Available in XS – XXL
Button Wrap Pocket Skirt
This Button Wrap Pocket Skirt has a trench coat-inspired design, and I think it’s fabulous. The structured details give it a polished yet unexpected feel. Keep it simple by pairing it with a slim-cut long-sleeve white or black top or tee, letting the skirt be the focal point. A pointed-toe shoe, like the one featured in the styling, is the perfect finishing touch.
Button Wrap Pocket Skirt
Ann Taylor
$90.30Available in regular and petite in sizes 00 – 20/22
The Skinny Trouser Pant in Stretch Cotton — Curvy Fit
I’ve been getting more requests for return-to-office options, and while I’m working on a more in-depth post, I’m keeping it top of mind in my daily recommendations. If you’re looking for a well-fitting trouser that won’t break the bank, the Skinny Trouser Pant in Stretch Cotton – Curvy Fit is a great option. It offers a classic slim-straight cut with a bit more room in the hips and thighs, making it a flattering and comfortable choice for the office.
The Skinny Trouser Pant in Stretch Cotton — Curvy Fit
Ann Taylor
$83.30Available in regular and petite in sizes 00 – 20/22.
Weekend Collection Striped Henley Sweatshirt
Another great find from Ann Taylor’s Weekend Collection, this Striped Henley Sweatshirt is made from a soft cotton blend and comes in a rich dark green stripe—which I love. Green is showing up as a versatile neutral this season, making it an easy addition to any wardrobe. I ordered this to pair with light and medium-wash jeans and low-profile sneakers for a relaxed yet put-together spring look.
Weekend Collection Striped Henley Sweatshirt
Ann Taylor
$62.65Available in regular and petite in size XXS – XXL
The Hutton Blazer in Brushed Rib Knit
I’m really looking forward to wearing the Hutton Blazer in Brushed Rib Knit, done in a soft neutral beige. This casual, single-breasted blazer is effortlessly versatile—you can wear it just about anywhere. Heading back to the office a few days a week? Pair it with trouser jeans for a polished yet relaxed look. Running errands in the spring? Throw it on as a light layer over light-wash jeans and sneakers. It’s a great wardrobe staple and currently on sale for $125.
The Hutton Blazer in Brushed Rib Knit
Ann Taylor
$123.20Available in regular and petite in 0 -18.
Weekend Collection Stitched V-Neck Cardigan
If yellow is in your color wheelhouse, may I suggest the Weekend Collection Stitched V-Neck Cardigan? It’s also available in white and classic navy, but the yellow stands out as a fresh, happy hue—the perfect pick-me-up after a long, dreary winter. This shade would look especially chic paired with dark ink-wash trouser jeans (these J.Crew ones are a current reader favorite).
Weekend Collection Stitched V-Neck Cardigan
Ann Taylor
$45.00Available in regular and petite in XXS – XXL
Caged Kitten Heel Leather Sandals
Surprisingly, I’ve had a lot of luck with Ann Taylor shoes over the years—I find them to be well-made and stylish. So when I came across the Caged Kitten Heel Leather Sandals, I didn’t hesitate to grab a pair. I’ve been looking for something like this for the past few seasons, but every option I found had a heel that was just too high. At 5’10”, I don’t need much extra height, but a little lift is always nice.
I love the versatile color, which works as a neutral for everyone, making it easy to style with dresses, skirts, light-wash jeans, and linen bottoms.
Caged Kitten Heel Leather Sandals
Ann Taylor
$103.60Available in sizes 5 – 12
Straw-Wrapped Drop Earrings
I don’t usually go for accessories from stores like Ann Taylor or J.Crew—you can often find better, more affordable options elsewhere. But I do like to keep an eye out for “dupes” of novelty pieces from brands like Tuckernuck—I love their jewelry, but it’s often a bit too oversized and pricey for what it is.
These Straw-Wrapped Drop Earrings are a great alternative for summer—lightweight, stylish, and perfect with a linen outfit, whether it’s a matching set or an easy dress.
Straw-Wrapped Drop Earrings
Ann Taylor
$48.65
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