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21 Loose Fall Dresses to Look Like a Rich Hamptons Aunt

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My life goal is to be the rich aunt with the most impeccable style. I already live up to that reputation with my impressive selection of Amazon dresses. Yes, Amazon has a surprising selection of high-end dresses that many people assume I bought at outlets in the Hamptons.

The options for fall are also incredible right now, with a mix of deep hues, comfortable fabrics and flattering silhouettes. Get into the rich aunt vibe with these 21 loose-fitting fall dresses today.

21 Loose Fall Dresses to Look Like a Rich Hamptons Aunt

1. Make it a Midday: All the rich aunts in the Hamptons go to wine weekends wearing dresses that look exactly like this ruffled midi.

2. Chocolate Brown: This rich hue is the color of the season, and this cozy waffle knit maxi from Anrabess will help you stay on trend.

3. Baby brunch: Pair this casual tunic dress with tall boots, a leather jacket, and pretty gold accessories, and you’ve got the perfect outfit for all fall activities.

4. More comfortable than sweat: Sweatpants can look moody, but if you take the same fabric and turn it into a ruffled dress, you’ll be the most stylish person in the room.

5. Navy Dreams: Darker colors are a must-have in fall wardrobes, and yours won’t be complete until you add a long navy t-shirt dress to your collection.

6. Dress it up: You shouldn’t need an excuse to wear this gorgeous low-waisted pleated dress: it’s time to make every day a party!

7. Pumpkin Spice: Match your favorite fall latte by snagging this long-sleeve t-shirt dress from Sampeel in a rusty caramel color.

8. Bohemian Beauty: The floral pattern of this smocked midi dress will keep you in a good mood when the temperatures drop. Don’t worry, the deep orange and yellow colors make it perfect for fall.

9. Haute Couture: This unique flowy sweater dress combines a variety of design elements, including a pleated skirt, sweater top, and Breton stripes, for a fresh-off-the-runway preppy look.

10. Extra comfortable: You’ll want to snuggle up in this sweater dress all season long. Best of all? It has pockets!

11. Readiness Star: Look like you’re headed to an expensive British boarding school in this ribbed sweater dress. The adjustable quarter-zip neckline is our favorite detail.

12. Swing Swing: The bell sleeves of this lightweight knit dress give a totally ’70s vibe. If you have winter weddings on the schedule, this will definitely come in handy.

13. Cute and affectionate: The babydoll cut and square neckline make this flowy ribbed sweater dress ideal for date nights. It flatters your figure while keeping you warm.

14. Red red wine: Dark burgundy is an inherently sophisticated color, which is why you need the Zeagoo sweater dress for special dinners this season.

15. Total theft: For a limited time, you can purchase this colorblocked sweater dress for just $15! It’s definitely worth becoming your new go-to.

16. Home Basics: What do all the rich aunts wear at home? The answer isn’t athleisure, it’s this relaxed tunic dress. The under-$25 piece is literally softer than pajamas.

17. All in the details: The intricate embroidery on the neckline makes Dokotoo’s shift dress look much more expensive than it actually is.

18. Simple classic: You can never go wrong with an oversized sweater dress. Our advice? Choose a fun color! This one is available in pink, orange and wine red to boost your mood.

19. Very chic: You look like you just stepped out of a Ralph Lauren Polo commercial in this pinstripe collared sweater dress.

20. Super Stackable: It’s not always easy to wear a leather jacket over long-sleeved dresses. We suggest you opt for this model with puffed sleeves which will look very cool with a motorcycle jacket and combat boots.

Cute cable knit: You can never go wrong with a timeless cable knit sweater dress – period. This one will stay in your closet for decades.

Related: 21 Loose, Flattering Dresses That Embody Fall Hamptons Style

Hamptons style is all about looking effortlessly chic with relaxed silhouettes, rich seasonal hues, and just the right touch of understated luxury. And the right dress can transport you there instantly. Hamptons-style fall dresses have the most flowy, flattering silhouettes, polished enough for a dinner date, but easy enough for a stroll. […]

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