When it comes to looking expensive without trying, Upper East Side moms have mastered the art. Just walk down New York’s Park Avenue and you’ll see women in timeless silhouettes, rich-looking fabrics and the kind of sophistication that looks right out of Charlotte York’s closet. This season’s fall dresses deliver all of that and more; they’re the seasonal wardrobe update you’ve been looking for.
From chic wrap styles for a mid-day brunch to polished midi dresses that turn grocery aisles into a runway moment, these picks are both elegant and wearable. Below, we rounded up 17 rich-looking fall dresses that exude “Upper East Side mom” energy — but start at just $26.
17 Rich-Looking Fall Dresses to Look Like an Upper East Side Mom
School Drop-Off Ready
1. Our Favorite: Look chic while still staying comfy for school drop-offs in this ruched-waist midi that can easily be styled with a sleek pair of sneakers.
2. Stylish Staple: We’re willing to bet that every stylish New York mom has a flowy maxi dress just like this sitting in their closets right now.
3. Waist-Slimming: Subtly show off your curves in this comfy wrap dress that can easily be worn for running errands as well.
4. Figure-Skimming: The ultimate versatile dress, this bodycon midi dress can easily be switched out with sneakers for a pair of heels.
5. Pilates Princess: Go from school drop-offs straight to pilates in this long-sleeve athletic dress that also has a tummy-control tie waist.
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Elevated Brunch Vibes
6. Our Favorite: A number-one best-seller on Amazon, this embroidered maxi dress has designer-level details.
7. Chic Shirt Dress: Another staple of New York moms’ wardrobes, this sleek shirt-dress perfectly pairs with strappy heels and dainty gold jewelry for brunch.
8. Floral Fabulous: Florals for fall? This botanical-printed maxi actually might be the groundbreaking autumn dress you’ve been looking for.
9. Polka Dot Perfection: A wardrobe classic, this polka dot wrap dress is a style that can be worn on repeat throughout the fall season.
Weekend-Getaway Worthy
10. Our Favorite: Perfect for a quick fall getaway, this comfy midi dress is made for staying comfortable throughout long days of travel.
11. Timeless Twist: Embrace warm fall days with this coastal-inspired dress that looks straight out of the Hamptons.
12. Cottagecore-Chic: With soft lines and rustic charm, this belted shirt dress channels major countryside escape energy.
13. It’s Giving First Class: This waist-slimming midi is made for traveling first class — simply add oversized sunnies and a chic tote.
Polished Office Picks
14. Our Favorite: Go straight from the office to happy hour with this sheer wrap dress that masterfully blends effortless style and nighttime allure.
15. Polished Prints: Nail office fashion with this stunning printed dress that serves designer-boutique vibes.
16. Belted Beauty: New York women love a pop of eclectic prints, which is why we think they’d be drawn toward this two-tone belted pick.
17. Pleated Perfection: Perfect for transitional weather, this pleated wrap dress is made of a lightweight knit that’s just warm enough for fall mornings.
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