Fall fashion has a grounding effect, encouraging you to look inward. It features warm wool coats, heavy denim, cashmere knits, and sturdy boots that offer both physical and emotional stability.
This feeling of being grounded can be especially vital if you reside in a city dominated by concrete, sirens, and scarce greenery. In such environments, fashion plays a crucial role. By taking inspiration from charming rural areas and adopting the style there, you can trick your mind into feeling as if you’re in those peaceful settings—even while riding the subway. This approach embodies the New England style fashion trend for fall 2025.
Forget Parisian style; fashion people everywhere are already all over New England style. It includes wearing a cable-knit sweater and cashmere socks that look cozy next to a fireplace in a Vermont log cabin, a striped sweater and jeans suited for a stroll through Rhode Island, or a crisp plaid button-down shirt with pants tucked into riding boots for horseback riding in New Hampshire.
We’re seeing these preppy and equestrian-inspired designs appear in the closets of in-the-know fashion people as well as in the collections of designers like Dairy Boy. The Connecticut-based brand founded by influencer Paige Lorenze launched its fall collection, Evergreen, inspired by Lorenze’s New England roots. “The collection is really authentic to my childhood,” Lorenze tells Who What Wear. “It’s inspired by sport, nostalgia, utility wear, and all the things I used to love and use.” There’s a selection of colorful fleeces, barn jackets, tailored button-down shirts, plaid dresses, rugby shirts, and denim overalls. What’s ironic is that many of these styles nod to the top fall and winter trends. However, Lorenze notes that that wasn’t intentional. “It’s great that a lot of the pieces in the collection relate to what’s trending, but it doesn’t feel like we are chasing that [the trends],” she says. “It really feels like it’s part of our story—authentic to the Dairy Boy brand.”
While many pieces in the Evergreen collection, as well as part of the New England fashion aesthetic, are simple in design, Lorenze understands that adopting a new way of dressing can feel overwhelming. To make the style easy and approachable, she suggests starting with a white top, whether a simple button-down, a tartan shirt, or a waffle long-sleeve, and styling it with wardrobe essentials like flare jeans and a cute belt. Inspired to experiment with the New England fashion aesthetic? Keep scrolling to find inspiration from chic fashion people already embracing the trend and shop the essentials needed to re-create their looks.
Discover New England–Style Outfits for Fall
New England’s signature fashion style doesn’t fully embrace Western aesthetics, but influences from the region are there, especially during fall. An easy example is a simple denim outfit featuring a Western-inspired belt, as shown in the image above. To keep the accessory grounded, pair it with classic silhouettes, such as a white button-down shirt and straight-leg jeans.
Shop the essentials below:
Nordstrom
Cotton Poplin Button-Up Shirt
Madewell
The Longline Straight Jean
Ralph Lauren Collection
Rodeo Buckle Vachetta Leather Wide Belt
Free People
Blaze Pull-On Boots
(Image credit: @georgia_3.0)
Whether you’re heading to rural New England or aiming to capture its quaint, charming, and calming atmosphere, you’ll need a pair of riding boots, the top shoe trend for fall 2025. Keep the elegant nature of the boots by pairing them with crisp jeans, a blazer, and a preppy baseball cap from Ralph Lauren.
Shop the essentials below:
Polo Ralph Lauren
The Iconic Cotton Chino Ball Cap
J.Crew
Slim-Straight Jeans
Madewell
The Essential Leather Belt
When thinking of New England, you might picture loafers, collegiate sweaters, or nautical-inspired pieces such as striped and navy tops. Yet traditional preppy elements like plaid or tartan remain popular. Luckily, with the check print being a major fall trend, there are plenty of options, especially for tops. To elevate a plaid shirt from casual to dressy, pair it with tailored trousers, a leather pencil skirt, and boat shoes or pumps.
Shop the essentials below:
proenza schouler
Bronwen Top
Banana Republic
Straight Ponte Pull-On Pants
aritzia
x Sperry Authentic Original Boat Shoe
(Image credit: @daniellejinadu)
Another chic outfit formula for days spent touching grass is tailored pants or Bermuda shorts and knee-high leather boots. On top? Opt for a lightweight jacket or a plush cardigan.
Shop the essentials below:
Anthropologie
The Juliet Cashmere Cardigan Sweater
ZARA
Wide Leg Pleated Pants Zw Collection
Massimo Dutti
Leather Riding Boots
When it’s wet outside, creating a practical yet stylish outfit can be challenging. A reliable option is to pair a barn jacket with knee-high rubber boots. The latter is especially important, as fashion people, particularly in London, are all over the boot trend. While many opt for Hunter boots, there are also elegant alternatives available from brands like Scarlett Chase and Fendi.
Shop the essentials below:
Banana Republic
Barn Coat
GUIZIO
Calesia Knit Shorts
Scarlett Chase
Aurora Boots
(Image credit: tk)
This fall, instead of edgy leather jackets, fashion people in NYC, L.A., and Paris will be embracing plaid outerwear. The style draws inspiration from The Row’s Tavishina jacket, which sold out immediately in the spring; however, other designers like Reformation, Sézane, and Madewell have put their own spin on the design, offering alternative options for everyone.
Shop the essentials below:
AFRM
Jasmine Stirrup Pant
Freja New York
Mercer Bag Berry Croc
Dairy Boy’s new collection features stylish rugby shirts that capture New England’s fall look. Wear them casually with boxer shorts and socks, as shown in the brand’s campaign, or dress them up with a suede midi skirt and slingbacks.
Shop the essentials below:
Dairy Boy
The American Rugby
Skims
Cotton Poplin Sleep Shorts
You can’t go wrong with a classic and elegant cable-knit sweater. Style it like Lorenze did with an Oxford shirt, knit shorts, ankle socks, and suede loafers.
Shop the essentials below:
Jenni Kayne
Cable Serena Crewneck
The Row
Soft Moccasin in Suede
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