There’s something so elevated yet relaxed about New England-style dresses. It could be the coastal vibe, or maybe it’s the breezy go-with-the-flow aesthetic — either way, we’re all in on the look.
The preppy, beach town style makes Us instantly think about rich moms hopping on yachts, browsing farmer’s markets, playing pickleball and dining beachside. And these exact dresses will make you look like you do the same. With lightweight fabrics, pastel colors, fun patterns and an overall feminine appeal, each pick on our list gives you that old money style you can only inherit. Hey, fake it ’til you make it, right?
Our favorites come from brands hanging in a Nantucket rich mom’s closet, including Tuckernuck and Hill House Home. However, you’ll also find inspired looks from retailers you probably already shop from like Amazon, Walmart, Abercrombie & Fitch and Quince — starting at $17.
New England-Style Dresses to Look Rich
1. Our Favorite: A-line dresses can be spotted everywhere from Newport to Cape Cod, so naturally, we had to get one to look the part. This top-rated dress has an elasticized waist that feels comfy and stretchy, while also giving you an hourglass appearance. We especially like it in this expensive-looking light blue hue.
2. Runner-Up: Gingham is back in full force for spring, so might as well get in on the trend with this spaghetti strap dress. The neutral khaki color palette makes it easy to style — wear it with a sweater draped on the shoulders, throw on a denim jacket or layer on fun boutique-worthy jewelry. The choice is up to you.
3. Going Viral: This midi corset dress combines two spring trends in one, making you the coolest gal on the block. The peasant-style bodice is extremely popular due to the Wuthering Heights fandom, and the butter yellow hue is so trendy that it’s even getting celeb attention. Just look at Martha Stewart‘s recent outfits.
4. Playful Pattern: Can you ever go wrong with a floral dress? We think not. This easy-going find is perfect for boozy brunches, errand runs and the like. Oh, and the ruffle cap sleeves and fit-and-flare skirt make it so flattering, too.
5. Game Changer: We love just about everything about this expensive-looking dress, from the body-hugging bodice to the free-flowing maxi skirt. But what makes it stand out from the crowd is the rick-rack trim. The retro style gives the dress a playful touch while also alluding to the beachy waves.
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6. Quite the Charmer: Lilly Pulitzer is all about that bright, fun energy. And while some patterns can be a bit too bold for the New Englander, this pretty pink and green option is just right. It also has that classic collar neckline with a cute ruffle trim at the bottom.
7. Warm-Weather Staple: Linen dresses under $100 are hard to come by . . . until you browse the selection on Quince and find this little number. Made with European linen, this gorgeous pick delivers breathability and effortlessly rich style. Hello, the mariner stripe print is begging to be worn on the water.
8. Designer-Looking: If you look at this Quince dress quickly, you’ll think you just stumbled upon the Hill House Home Nap Dress. The dainty floral pattern, ruffle straps and smocked bodice exude ‘Cape Cod rich.’
9. Pop of Color: Abercrombie’s Mila Midi Dress is giving total Americana vibes — just with fun extra embellishments that make it feel fresh for spring 2026. The red gingham pattern is perfect on its own, but the little strawberry adornments? You can’t get any cuter than that.
10. Expensive-Looking: Finding a coastal Tuckernuck dress at this price point is almost unheard of, which is why we snapped this one up ASAP. The midi dress looks like a top and skirt combo that stylists can approve of. The colors aren’t exactly the same, which actually makes it feel so cool. Only you’ll know that this find is actually a dress you threw on in five seconds flat.
11. Sporty-Chic: Whether you’re golfing on the course or running errands, do so in this classic preppy athletic dress. In addition to its relaxed fit and lightweight feel, the dress also has SPF protection to block the sun’s UVA and UVB rays.
12. Last But Not Least: Anyone who wants the real quintessential Ellie Nap Dress is in luck because Hill House Home is having a sale on several pieces, including the famous style. The legendary find feels like luxury in clothing form, thanks to the breathable cotton fabric, billowy fit, ruffle sleeves and smocked top. The pretty patterns don’t hurt, either.
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