You don’t need a cottage in the Northeast to imagine the classy Boston aesthetic. From fashion to decor, everything is preppy, polished and luxe — but nothing steals the show quite like boutique-style winter dresses on Newbury Street. Luckily, you don’t need a plane ticket to get the look. Our favorite East Coast-inspired dresses are secretly on Amazon, and they start at just $11!
Even better, these affordable picks are as flattering as they are stylish. With cozy fabrics, drapey silhouettes, high waistbands and lengthening details, these dresses masterfully conceal bloating, bumps and other insecurities. Whether you’re looking for a casual errand dress or a head-turning date night outfit, these Boston-style dresses step up to the plate.
Boston-Style Dresses on Amazon
1. Everyday Outfit: Classy, stretchy and mega versatile, this long-sleeve maxi dress checks every box. It’ll carry you from daytime appointments to relaxed winter weddings.
2. Could Be Cashmere: Everything about this wintery A-line dress looks expensive, especially the wool-blend material and pleated midi skirt.
3. Boutique Aesthetic: Eyelet detailing gives this maxi dress a boutiquey flair. The cinched waist and hidden pockets add to the appeal.
4. Pretty and Preppy: Look like you graduated from an Ivy League school in this cable-knit sweater dress that’s enhanced with a flirty chiffon skirt.
5. Check Yes: Swap your errand outfit for this casual plaid dress that feels like loungewear . . . but looks so elevated.
6. Curve-Skimming: If you’ve got it, flaunt it! This fit-and-flare maxi dress cinches without squeezing, giving you an effortless hourglass appearance.
7. Modest Maven: Nothing screams ‘old money’ like this mock-neck maxi that secretly lengthens the torso, thanks to an exposed front seam.
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8. Just $26: We’d say this V-neck sweater dress is the definition of East Coast style. It features a cable-knit design, sporty striped hems and a relaxed fit.
9. Year-Round Staple: Love pastels? This colorful maxi dress is perfect for every season. You’ll wear it to birthday bashes, farmer’s markets and everything in between.
10. Striped Up: If Free People and J.Crew had a fashion baby, it would be this stripe-hem sweater dress that gives any wardrobe some character.
11. Tastefully Oversized: This drapey knit maxi dress is as comfy as it looks (if not comfier). Compliments are guaranteed, so keep the link on-hand.
12. Trendy Turtleneck: Everyone needs a staple turtleneck, and this cable-knit sweater dress is the upgraded version.
13. Tailored Appeal: Gold buttons, decorative pockets and intricate stitching are just a few highlights of this one-of-a-kind dress. Don’t forget to check the coupon box!
14. Rich Mom: Conceal your tummy while elevating your look in this ribbed maxi dress. It features a high waist, striped skirt and darling bow-tie waist.
15. Total Trendsetter: Why choose between a top and a dress when you can have both? This corduroy-style mini dress layers beautifully over any fitted top.
16. Neutrals, Please: If you want to look like a Boston socialite, you can’t go wrong with this beige and black dress that embodies quiet luxury style.
17. Figure-Hugging Find: Dozens of shoppers describe this sexy yet sophisticated dress as mega flattering. It hugs all the right places!
18. Dinner Party: All you need is this belted turtleneck dress and a glass of champagne to look like a multimillionaire.
19. Polo Style: This fuzzy polo dress reminds Us of Lauren Ralph. It gives off designer vibes while looking ‘collegiate cool’ at the same time.
20. Snowbird Central: Live somewhere warm? Opt for this frilly short-sleeve pick that’s feels wintery yet lightweight.
21. Classic Quarter-Zip: Stripes, embroidery, shiny hardware, oh my! This long-sleeve mini dress makes every outing Boston Common-worthy.
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