There’s a certain something special about dressing like the aunt who dresses for the holiday function with pieces that scream ‘impeccable taste.’ She’s relaxed, refined and always looks like she came straight from a long weekend in the Hamptons. Fortunately, recreating her style doesn’t require owning a beachside estate — not when you can shop these affordable picks instead.
These 19 loose fall-to-winter clothes will give your closet that breezy-rich feel, without the designer price tag. Think pleated knit dresses, quiet luxury crewnecks and chic poncho shawls that feel elegant but unfussy. Scroll on for stylish staples work for errands, evenings out and everything in between — starting at only $7.
19 Loose Fall-to-Winter Pieces to Look Like a Rich Hamptons Aunt
Darling Dresses
1. Our Favorite: If anything screams ‘rich aunt chic,’ it’s this pleated knit dress with its cozy feel and preppy finish.
2. Stunning Stripes: For that quietly luxurious vibe, this striped knit maxi dress does it best.
3. Cocktail Classic: With its refined draped hook accent, this midi cocktail dress is perfect for any upscale occasion.
4. Dreamy Velvet: Tap into autumn glamour with this luxe velvet dress, which is offered in several rich, statement-making shades.
5. Off-Shoulder Chic: For a chic winter go-to, opt for this off-shoulder knit dress that’s great for brunches or fancy dinners.
6. Mocha Must-Have: Made with a cozy ribbed knit, this Quince mocha midi dress embodies fall’s most elegant, on-trend hue.
7. Holiday Hero: Made for the holiday season, this off-shoulder Old Navy dress shines thanks to its sleek gold twist accent.
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Tops and Sweaters
8. Our Favorite: Elevate your everyday style with this rich aunt-style crewneck that easily passes for cashmere.
9. Oversized Perfection: Soft and slouchy, this oversized knit sweater brings a coastal elegance to any look.
10. Cozy Cable Knit: We think rich aunts would pair this cable knit turtleneck with tailored trousers and chic kitten heels.
11. Classy Cashmere: This Quince cashmere sweater delivers that indulgent, luxe texture without the usual designer price tag.
12. Posh Poncho: Not only does this luxe poncho shawl channel ‘total rich’ energy, it’s also a major Amazon shopper favorite.
Must-Have Matching Sets
13. Our Favorite: This designer-looking matching set brings a refined, understated elegance that feels subtly expensive.
14. Scandi-Inspired: Get the cool Scandinavian aesthetic with this contrast-detail knit set that feels sophisticated and snuggly.
15. Coastal Crochet: Nothing gives off a coastal feel like this crochet-knit set that looks straight out of a Hamptons boutique.
16. Free People-Inspired: Channel that laid-back Free People style with this waffle-knit set that looks far pricier than it is.
Polished Pants
17. Our Favorite: These drawstring jeans deliver the same laid-back, curated aesthetic you’d spot at Anthropologie.
18. Luxe Leopard: These luxe leopard-print jeans are an instant way to tap into that bold, artsy cool girl vibe.
19. Silky Stunners: These J.Crew silk pants are the simplest way to look polished while feeling incredibly comfortable.
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