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Home Entertainment

19 Summer Sundresses to Look Like a New York Rich Mom

by DigestWire member
June 28, 2025
in Entertainment
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19 Summer Sundresses to Look Like a New York Rich Mom
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New Yorkers — more specifically, Upper East Side rich moms — have bold, untouchable personas. These ladies live for galas, social clubs and benefits, and often split their time between Manhattan penthouses and Hamptons abodes . . . and they always dress the part. And flowy yet flattering sundresses? Those are always on deck for summer.

While some rich moms shop at Saks Fifth Avenue, we’re convinced many shop on Amazon. Some of the classiest, most expensive-looking sundresses we’ve seen are available with Prime shipping. They feature billowy silhouettes, sophisticated designs, boutique-inspired details, starting as low as $20. So whether you’re shopping for everyday outfits, the office or a wedding, these 19 dresses are ones to consider.

Everyday Dresses

1. Our Favorite: Simple, stylish and effortlessly polished, this button-front dress (with flutter sleeves!) is the definition of rich mom.

2. Totally Timeless: Look put-together in this classic midi dress that has a tiered skirt, ruffle sleeves and secret pockets.

3. Nautical Twist: This casual waist-cinching dress gives yacht wife energy, making it a must for any summer vacation.

4. Not Your Typical Tee: Nail a laid-back “chill girl” aesthetic with this breezy T-shirt dress that smooths the midsection and hips.

5. Beach Day: Combine Outer Banks and Southampton with this breathable, ultra-soft maxi. It’s totally boho chic.

6. Preppy Chic: Front buttons, flare sleeves, ruffles and a foldable collar are just a few highlights featured on this mini. We bet you’ll wear to the farmer’s market and beyond.

7. Linen Look: Flattering is an understatement with this billowy belted maxi that instantly conceals bloating.

8. Touch of Santorini: Unleash your inner prep in this tiered maxi that has dramatic puff sleeves and a button-front design.

I Can’t Believe These 19 Designer-Looking Summer Blouses Are All Under $20

In-Office Dresses

9. Office Envy: Stun from the cubicle to happy hour in this flutter-sleeve maxi dress. It pairs beautifully with strappy sandals!

10. Country Club: Have you ever seen such a sophisticated outfit? This classy mini has gold hardware, decorative pockets and a creamy beige hue.

11. Casual Friday: Wear this knee-length dress with a blazer, tights and flats for the ultimate corporate getup.

12. Luxury Long-Sleeve: The chiffon material keeps you cool while you file, type and make small talk at the coffee machine.

13. Dainty Queen: This solid-color wonder is one-of-a-kind with a darling neck tie and pleated material. It seriously looks designer.

14. Simply Smocked: Hidden pockets are just one thing we adore about this square-neck maxi that doubles as a brunch dress.

15. No Frills or Fuss: Polished and classy, this ruffle-sleeve midi dress exudes put-together energy wherever you wear it.

Wedding Guest Dresses

15. Guest of Honor: Eyelets, pleats, tiers, oh my! This pretty pink outfit has a loose, flowy silhouette that doesn’t squeeze, poke or highlight insecurities.

16. Swiss Dots: The Swiss dot details never go out of style. You’re guaranteed to look wealthy in this luxurious long dress.

17. Bodycon Style: Many bodycon dresses aren’t flattering, but this one hugs only the best places while hiding bumps with ease.

18. Outdoor Wedding: Picture wearing this tiered short-sleeve maxi at a beach wedding or a garden-themed soiree. Chic, right?

19. Steal the Spotlight: Shiny and ribbed, this lengthening maxi dress will make you look and feel like a supermodel.

18 Colorful Amazon Dresses to Look Tan, Slim and Confident This Summer

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