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North of the Manhattan madness, you’ll find a quiet haven of old money living, which includes sprawling family estates, acres of rolling land and country clubs in every town. Equal parts timeless, rustic and luxe, upstate New York fashion is just as swoon-worthy as the aesthetic, and I found 17 stylish fall pieces that could be straight out of a Tuxedo Park boutique.
Classy wool sweaters, Chelsea boots, straight-leg jeans and tailored-looking dresses are just a few staples in every upstate rich mom’s wardrobe, and these styles get you the look. Whether you’re running errands, apple picking or leading a boardroom meeting, these elegant picks make you look rich while doing it.
17 Upstate New York-Style Fashion Pieces — From $5
Classy Tops
1. My Favorite: Chic is right! I love how this mock-neck top transitions seamlessly from summer to fall, thanks to the wool-blend fabric and sleeveless design.
2. Classy Cowl: Instead of a tee, opt for this drapey cowl-neck blouse that not only elevates your aesthetic, but also conceals your tummy.
3. Wardrobe MVP: Solid and sophisticated, this knit short-sleeve top pairs well with jeans, trousers and skirts alike.
4. Business-Casual: Your colleagues will assume you spent triple digits on this polished blouse, thanks to the refined print, bell sleeves and subtle pleated detailing.
Polished Pants
5. My Favorite: Nobody will ever guess these dressy wide-leg trousers have an ultra-stretchy waistband. I won’t tell!
6. Totally Tailored: This straight-leg denim style is everywhere in London, so it makes sense that rich New Yorkers are catching on.
7. Cute and Cropped: Lean into the the cropped pants trend with these trendy wonders that hit at your shin to avoid going full capri.
Pretty Dresses
8. My Favorite: Bell sleeves, bow knots, ruching! This boat-neck mini dress works for date nights and work events. Just add tights for the latter.
9. Polka Dots: Everyone’s wearing polka dots lately, so it’s no surprise that this wrap-style midi dress is flying off the shelves.
10. Burgundy Babe: Fitted dresses aren’t always flattering, but this slimming version has vertical gold buttons that secretly elongate your torso.
11. Silky Satin: Weddings call for this dreamy satin maxi dress that feels like wearing nothing at all. With 30 options to choose from, I want at least two.
Must-Have Shoes
12. My Favorite: These suede loafers are the easiest swap for sneakers, channeling high-end vibes while keeping your feet cushioned.
13. Ankle Boots: Something between Chelsea boots and booties, these block-heel kicks bring the best of both worlds.
14. Slip-Ons: If you’re curious what Tuxedo Park socialites wear, it’s sleek leather mules that elevate even the most basic jeans.
15. Celeb-Inspired: Ever since Angelina Jolie wore two-toned flats, I’ve been eyeing this Project Cloud pair.
Sleek Layers
16. My Favorite: Cardigans can look frumpy but not this wool-blend number that fits every body like a glove.
17. Quiet Luxury: Quilted puffers are a staple upstate. I appreciate this equestrian style that brings Millbrook to the Midwest.
