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Home Entertainment

Look Like a Hamptons Mom in These ‘Casual Rich’ Dresses — Starting at Just $18

by DigestWire member
November 6, 2025
in Entertainment
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Look Like a Hamptons Mom in These ‘Casual Rich’ Dresses — Starting at Just $18
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Whether you’re headed to the office, lunch with friends or a formal occasion, you’ll need dresses that work with every event this fall. Of course, you want your clothes to look like you shopped at a Hamptons boutique, even if the price tags don’t reflect that. So, we went on the hunt for expensive-looking dresses that cost less than $50.

Time and time again, Amazon proves to be a place to find hidden gems, and this is no exception. After browsing through our picks, you’ll notice that these dresses are stylish, flattering and warm. Oh, and they give off that effortless Hamptons rich mom energy we love. Score ‘casual rich’ dress picks, as we like to call them, with either long or short sleeves, so you can dress appropriately for both warm fall days and chilly winter evenings. The best part? These luxe-looking dresses start as low as $18.

16 ‘Casual Rich’ Dresses That Give Off Hamptons Energy

1. Our Favorite: Wear this knee-length tiered dress with boots for a casual look or heels for a dressed-up option — the choice is up to you. This pick has a unique neckline and versatile sleeves, so you’re always comfortable.

2. Best Basic: Consider this your go-to dress when you need a simple long-sleeve option. It can be layered over with a blazer, cardigan or pullover for extra warmth.

3. Sweater Weather: It wouldn’t be fall without a chunky sweater dress, and this one has the classic cable knit stitch for a familiar style.

4. Must-Have Midi: It’ll look like you put together a cute outfit, even if you just threw on this long-sleeve midi dress. Yep, it appears to be a skirt and a top, but we won’t tell.

5. Cute Crochet: What appears to be a rather basic long-sleeve dress is spruced up with the crochet detailing up top that catches the eye.

This Secret Hub Is Packed With Luxe-Looking Pieces (That Are Secretly Affordable!)

6.  Very Versatile: Hitting just below the knee, this long-sleeve A-line dress has a flattering square neckline and ribbed texture, making it the best $18 you’ll spend this season.

7. Memorable Maxi: You won’t have to worry about adding a cardigan with this ribbed maxi number. It has a stretchy knit material that makes it warm and comfy for all-day wear.

8. Trendy Tie: To give your body more shape, utilize the waist tie on this knee-length wrap dress, and you’ll be ready for work, play and beyond.

9. Pretty Plaid: For something a little different, this cowl neck long-sleeve dress has pops of plaid detailing and patch elbows for a fall-ready option.

10. Lovely Layer: You can create different looks when you have a pullover vest dress, like this sweater option. It works well under a simple long-sleeve top or button-up shirt.

11. Flowy Find: A long-sleeve maxi dress will serve you well during the colder months, as it’s versatile and can be paired with a range of footwear.

12. Cute Collar: With cable knit on top and pleats on the bottom, this collared sweater dress is unlike anything you already have hanging in your closet.

13. Real Ribbed: A sweater dress doesn’t have to be fitted, as proven with this flowy ribbed option that has button details on one side for extra flair.

14. Cool Color-Block: This $32 short-sleeve dress looks like you spent time styling it, thanks to the color-blocking detail that makes it look like a shirt and buttoned skirt outfit.

15. Office Ready: If your favorite to-the-knee dress and button-up shirt had a baby, it would be this flowy long-sleeve find with ruffles at the hem for a feminine touch.

16. Size-Inclusive Pick: This lightweight maxi dress is available in sizes large to 3XL, and comes in plenty of solid colors and patterns for the look you like.

17. Perfectly Pocketed: There’s no limit to the places you can wear this long-sleeve midi dress, which comes in ten colors and, wait for it, has pockets!

Upgrade Your Closet With These Comfy Thanksgiving Dresses for Women in Their 40s

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