17 Loose-Fitting Dresses That Prove Style Gets Better After 40

From Jenna Lyons to Sarah Jessica Parker, celebrities keep proving that style only gets better as we age. They’ve also shown Us that it doesn’t mean sticking to uncomfortable bodycon styles you wore in your 20s — free-flowing silhouettes can be just as chic, if not more. From stylish silky numbers to fabulous floral picks, these 17 loose-fitting dresses are evidence that style after 40 is anything but boring.

Whether you’re someone who needs beautifully billowing dresses for brunches or cozy casual styles to wear at home, you’re going to love our finds below. The benefit of loose-fitting styles is that they softly drape over the body without suffocating you and are easy to wear — no constant readjusting here! Plus, you can style them up with cute accessories like waist-cinching belts or statement clutches.

The best part? These luxe options start at just $18.

The 17 Best Loose-Fitting Dresses for Women Over 40

Brunch-Ready Dresses

1. Our Absolute Favorite: Sip mimosas in style in this effortlessly elegant dress that comes in several pretty pastel colors.

2. Comfy and Cute:  This smocked mini dress is made of soft, stretchy fabric and combines a comfy feel with a chic silhouette.

3. Floral and Fabulous: Embrace the fresh spring energy with this floral tie waist midi dress, which pairs well with heels, sneakers and tennis shoes.

4. Polished Perfection: Prettygarden’s tiered ruffle maxi dress has so many chic elements we don’t know where to begin! Between the front buttons, collared neck, tie waist and contrasting trim, it’s bound to be a seasonal favorite.

5. Pretty Prints: From bright and vibrant styles to pretty pastels, this colorful puff sleeve dress comes in a variety of cute prints.

6. Stylish Stunner: This stunning smocked dress looks like something you’d spot at a luxury boutique — we can’t believe it’s just $50!

Relaxed Day Dresses

7. Our Absolute Favorite: This luxe T-shirt dress makes comfy fashion look so chic.

8. It’s Giving Rich Mom: Channel Hampton’s rich mom vibes with a flowy maxi shirt dress that can double as a beach coverup.

9. Has Pockets! Checking all the boxes, Grecerelle’s comfy maxi dress includes pockets and is made of a wrinkle-resistant fabric.

10. A Comfy Favorite: Perfect for afternoon drinks on the patio, this tiered, flowy T-shirt dress is super soft and stretchy.

11. Boho Beauty: Boho fashionistas will love the geometric print on this maxi dress, along with the cute drawstring details.

12. Doubles as Loungewear: With over 19,000 five-star ratings this soft and stretchy mini is beloved by Amazon shoppers.

Easy Evening Dresses

13. Our Absolute Favorite: Look fun and flirty in this flattering wrap dress that has a deep V-neckline and a cinched waist.

14. Chic Shift Dress: Pair this eye-catching shift dress with heels, gold jewelry and a simple clutch for a relaxed date night look.

15. Silky Stunner: Upgrade your night date night style with this stylish silk maxi that’s smooth against the skin.

16. Boho-Glam Maxi: Blencot’s glamorous boho dress puts a sultry spin on free-spirited style.

17. Pleated Perfection: For a special night out, wear this pleated cape dress that oozes luxury.