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The top Westport, CT clothing stores

WEST, in downtown Westport

It may seem like all the best shopping is had online these days, but the robust selection of Westport, CT clothing stores says otherwise.

While Westport’s downtown has undergone some turnover in recent years, there are still plenty of spots to shop.

There are a few areas of Westport where shopping is concentrated. The biggest is along Main Street, where you’ll find larger chain retailers like the Gap, Lululemon, J. Crew, Anthropologie, and Madewell, along with a few boutiques, all tucked among some of Westport’s best restaurants.

Aside from Main Street, the Post Road is scattered with a variety of clothing shops, too, including the luxury department store Mitchell’s, along with resale shop Roundabout, and staples like Free People.

There’s plenty more where that came from, too. Here’s a list of the Westport, CT clothing stores we love.

Westport, CT clothing stores

In alphabetical order, here’s a rundown of the top spots to shop in Westport.


Founded in 1992 in Pennsylvania, Anthropologie has now expanded their collections across much of the U.S., Canada, and the U.K. Anthropologie’s target audience has always been affluent women in their 30s and 40s who are looking to express themselves beyond the realm of business-casual. Their bohemian-esque patterns and unique lifestyle pieces provide personality to the everyday closet and home of Anthropologie shoppers. Tops on their website average at about $100 per piece, making Anthropologie’s close far from cheap, but justifiable to purchase for the mindful, career-driven woman.

59 Post Rd. East, Wesport, CT

Around the Rosy Kids Consignment

Looking for kids clothes that are high quality but won’t cost a small fortune? Check out Around the Rosy. Around the Rosy is the ultimate kids consignment boutique for upscale and better children’s brands. Think Ralph Lauren, Lily Pulitzer, Boden, Petite Bateau, Chloe, Moncler, Burberry, etc).



Activewear designed intentionally with women in mind is Athleta’s niche, and they’ve done an excellent job at providing just that since their inception in 1998. Founded in California, they produce high-end sportswear for a variety of different purposes, from sports and exercise to loungewear and sleepwear. Athleta targets their collections for two different age groups; Athleta Women and Athleta Girl. Acquired by Gap in 2008, Athleta is part of a larger corporation but still strives for inclusivity and sustainability within their company. Athleta’s clothes are high quality and well priced for athletic wear, making them a top contender in the sportswear and athleisure fashion departments.



Recognizable for their waxed cotton jackets, Barbour is a luxury brand that specializes in countrywear for men, women and children. Barbour had its start in 1894 in the U.K., and now has a nationwide retail presence, while still remaining true to its roots in timeless British fashion pieces. Barbour creates what they call “lifestyle clothing”, essentially, clothing that is intended to be cherished and worn more than once. Their iconic waxed cotton jackets average at around $400, and they sell many more quality pieces, such as boots and leather gloves, to pair with this look for around $200 each. Barbour is a dream shopping destination for anyone looking to invest in quality clothing that stands apart from today’s trending patterns and fast-fashion lookbooks.


Bobbles & Lace

High end fashion that anyone can afford is the specialty at Bobbles & Lace, Massachusetts based women’s fashion retailer. Bobbles & Lace opened their first location in 2008, and have now expanded to eight brick-and-mortar locations, with an online presence as well. Comfortable, quality materials, monochrome tones and timeless designs are what make Bobbles & Lace stand out from the crowd. They follow fashion trends without rocking the boat, helping their styles stand the test of time and merging upper-scale fashion with shopping on a budget.


Brandy Melville

The idea for Brandy Melville was established in Italy in the 1980s, but didn’t take off until its launch in California in 2009, where it quickly gained traction among young women and teens. Although often described as trendy or relevant, Brandy Melville largely steers clear of promotional material, which in a way increases the aesthetic of the brand’s products as laid-back and effortless. Brandy Melville’s clothing is branded as “one size fits all”, which has caused controversy over the years, although Brandy Melville states that it is purely an eco-friendly and cost-efficient choice on their part. Young girls looking to live out their European daydream and lovers of casual fashion alike are quick to flock to Brandy Melville’s neutral, price-friendly tees, and this popularity likely won’t be stopping anytime soon.


Brooks Brothers

America’s oldest continuously operating apparel brand, Brooks Brothers, was founded in Manhattan in 1818, and they have made fashion history many times in their career. Brooks Brothers is well known for outfitting over 90% of the American presidents, and are considered a lasting authority on the style of the American people. They produce collections for men, women and children, and are also well-known for internationally sourced fragrances and finer luxury accessories. Brooks Brothers is known for classic American looks, and their pieces are best described as “timeless”. Although on the pricier side, with blouses averaging at just over $100, their reputation and quality make Brooks Brothers a reliable choice for the customer who wants to stand out by fitting in.


Brochu Walker

Los Angeles based label with French roots, Brochu Walker was founded in 2008, and is considered a conscious luxury brand. Conscious luxury in fashion comes down to a less is more mindset, and Brochu Walker does this swimmingly with a simple color palette and capsule collections sold by the occasion, so you always know just what you’re shopping for. Pieces at Brochu Walker average at about $400, making them not the most budget-friendly, but certainly a good place to shop for a statement piece. Brochu Walker is for the mature, sophisticated woman, who wants to feel good about where she’s shopping at, and what she’s shopping for.


Cloud 9 Designer Consignments

Cloud 9 Designer Consignments got its start as an online retailer in 2010, and has since transitioned to an in-person storefront in Connecticut for all your consignment needs. Cloud 9 offers a 50/50 split on products sold, which is a more fruitful rate for individual sellers than many consignment stores in the designer niche. Specializing in women’s designer clothing, including handbags and accessories, Cloud 9 Designer Consignments is a must-stop shop for anyone seeking out particularly quality statement pieces. Add a little spice and price to your wardrobe at Cloud 9 Designer Consignments.


Designer Label Consignments

Designer Label Consignments has been in business in Westport for more than 30 years, as a high-end clothing reseller. You’ll find everything from gently used Louboutin’s to Gucci and Tory Burch clothing, to affordable pieces from brands like JCrew, Madewell, and Theory. The store also has a large men’s consignment department.


Eileen Fisher

Eileen Fisher was founded in 1984 by, you guessed it, Eileen Fisher herself, and this designer-led women’s clothing brand says elegance and class like no other. Eileen Fisher expanded internationally in the early 2000s, and is known for a chic aesthetic in an easy-to-wear package. The brand targets middle-aged women, but has cross-generational appeal as well, with recent promotional action being taken to reach younger customers through sustainability movements. Eileen Fisher’s collections average at about $200 per piece, a price which customers are more than willing to pay for one-of-a-kind pieces that make a difference. For the mature woman who strives for comfortability, and for the young woman who desires grace and class, Eileen Fisher is the right place to be.


Fleet Feet

Fleet Feet got its start in California in 1972, and has since expanded across the U.S. to host almost 200 diverse locations. Fleet Feet is best known for their unique 3D foot-scanning technology, which they employ to ensure that you find the shoe which is just right for you. They carry a great range of popular brands, from Nike to HOKA ONE. Athletes of all kinds, from runners to hikers to gym fanatics, will be sure to find what they’re looking for in every size, style and color at Fleet Feet. Pick up your feet and head to the nearest Fleet Feet location to put some perfectly fitted pep in your step.



Connecticut-based women’s boutique, Fred, carries high-end, designer women’s styles in a warm and inviting setting. They also offer selections from their own private label, and are best known for comfortable blouses in muted patterns and classic, dark-wash denim to pair.

Fred is a Westport, CT clothing store that caters to the career-driven woman who knows how to relax and have some fun, which can be seen through their classic styles with a little bit of flair on the side. Prices average at about $300 per clothing item, and they also offer a wide variety of name-brand jewelry pieces from expensive designers such as GIGI CLOZEAU and Rachel Reid. If you’re looking for worldwide designer brands sold in a pleasing, homey setting, head down to Fred and see for yourself what this boutique is all about.


Free People

Nothing screams feminine and fun quite like Free People does, with collections that range from bohemian to chic, and an audience of twenty-something women longing for comfort and good vibrations in their clothing. Free People emerged from their parent company, Urban Outfitters, and became their own aesthetic, with flowy skirts, bralettes, and sandals to match. Free People embodies an energy of possibility and natural beauty, while still maintaining great quality in their clothing and manufacturing long-lasting pieces. Prices at Free People range from about $40 for a casual top, to $200 or more for a maxi dress — certainly pricier than fast fashion, while still remaining budget-friendly depending on the occasion.



Born and raised in the Bay Area in 1969, Gap is known as the largest specialty retailer in America, known for its laid-back styles and fashionable basics. Gap began as a company with a commitment to inclusivity, and this remains one of their core values from ethically sourced materials to fair labor laws to diversity in and outside the company. With a wide selection of clothes for men, women, and children, Gap caters to a large audience instead of focusing on quality in a particular niche. With new arrivals regularly dropping online and in-store, Gap remains relevant as a perfect stop for finding everyday leisurewear and quality casual clothing.


Great Stuff

If you’re looking for cozy sweaters, groovy patterns and a diverse color scheme, make sure to check out Great Stuff, a New-York based brand with locations also in Connecticut. Great Stuff is women-owned, family-operated, and prides themselves on providing an excellent customer experience, in-store and online. Great Stuff carries one-of-a-kind pieces from worldwide designers, making for a unique shopping experience that you won’t find anywhere else. Tops average at about $300, with pricier pieces like jackets and chic gowns reaching up to around $700; however, the high quality, re-wearability, and designer status of these pieces certainly justifies the price tag. Great Stuff is the perfect stop for anyone looking to diversify their wardrobe, or hoping to spice up an outfit with name-brand accessories to complete the look.



Intermix is the only luxury fashion destination you’ll ever need, with virtual styling sessions, designer sales and online lookbooks for the indecisive shopper in all of us. Founded in 1993 and acquired by GAP in 2012, Intermix has curated selections from designer brands and their own in-house collection.

Intermix’s brick-and-mortar location in Westport is aesthetically pleasing and highly curated, perfect for window shopping or browsing color-coded designer collections. Prices range from low hundreds to mid-thousands, but you can shop comfortably knowing the quality pieces that Intermix will deliver.


J Crew

If you’re looking for basics, J.Crew is the go-to. Founded in 1947 in New York City, J. Crew originally targeted upper-middle-class women seeking a sleek and mature look. J. Crew’s target audience has ebbed and flowed many times since then, sometimes struggling to keep up with the trends, yet remains relevant to this day by staying true to timeless preppy styles and quality pieces.

J. Crew is certainly an iconic American brand, being touted by celebrities and worn with pride, although they are still working to emerge from the dismal Covid-19 pandemic of 2020. J. Crew sell clothing and lifestyle collections for men, women and children, often at discounted prices, giving them multigenerational appeal as high-end clothing that’s affordable, too.


Johnny Was

Johnny Was is one of the liveliest of the Westport, CT clothing stores, and a staple in the boho-chic fashion community. It first opened its first location in Los Angeles in 1987, and expanded worldwide to over 1000 boutiques. The company is divided up into six main collections, each with their own niche, drawing inspiration from vintage aesthetics, global travels and western culture. Johnny Was designs clothes for the free-spirited woman, selling popular western themed tunics, swim and resort cover-ups, and kimonos, among other unique pieces. Stop by Johnny Was to stock up on outfits for an upcoming vacation, a night-out, or a day-in to boost your confidence and embrace the spirit of modern bohemian fashion.



Lululemon is the uniform of women everywhere. It was founded in Canada in 1998, and quickly expanded to serve markets across North America, Europe and Asia. Lululemon are the “it” brand in athleisure, especially to a younger audience, and they sell products for both men and women, with women being their primary focus. One way in which Lululemon quickly gained popularity with a younger audience is through the “scarcity model”; they only produce limited amounts of each product drop, so customers are inclined to buy them while they can instead of waiting for sales or price drops. Lululemon appeals to the twenty-something women who are interested in comfort and aesthetic, with trending loungewear and yoga sets that are quick to pop off the shelves.



If you’re in the market for flattering denim and neutral colors, Madewell is guaranteed to have just what you need. Founded in 1937, and acquired by the J. Crew brand in 2004, Madewell offers quality clothing which appeal to twenty-something women with an appreciation for tried and true fashion trends. Madewell sell a wide range of clothing, but are most known for their sustainable denim, casual shoewear and everyday fashion essentials. With prices averaging at about $100 for jeans and $75 for tops, Madewell secures themselves as an affordable brand without ever skimping on quality.


Marine Layer

You won’t ever want to buy a tee shirt from anywhere but Marine Layer, once you feel how uber soft, eco-friendly and stylish their shirts really are. California-based brand founded in 2009, Marine Layer is much more than just the softest shirt you’ll ever wear (although that’s definitely a plus). Their beach-friendly, sunshine aesthetic pieces for men and women will make you feel like you’re on vacation in the comfort of your own home. From basic tees and zip-up fleeces, to tropical swimsuits and resort sets, Marine Layer has a little bit of everything, all crafted with the brand’s signature comfortability and warmth. Marine Layer clothing is made with eco-friendly practices and California sunshine at heart, making it a must-stop shop for affordable styles you won’t want to take off.



Three generations of a family-operated business, and designer brands in an upscale setting are what make Mitchell’s unique. Based in Connecticut and expanded across the states, Mitchell’s brand philosophy is based on hard work, family values, and giving back to your community. This inviting environment certainly makes the brand’s designer prices more palatable, as they feature the work of name-brand designers such as Saint Laurent and Carolina Herrera. Luxury fashion in a family setting has helped the Mitchell’s brand really take off and inspire investment and shopping from tourists and locals alike. Expect to spend anywhere between $200 per piece to $2000 per piece, depending on which designer catches your eye, and rest comfortably knowing you’re sure to make waves wherever you go after shopping at Mitchell’s.


Paris Gordon

Paris Gordon is truly a woman’s best friend; an entrepreneurial fashion collection created with comfort, ease of wear and confidence in mind. Based in Westport, Connecticut, and with a popular online presence as well, Paris Gordon appeals to young and middle-aged women who love to love how they look. The most popular item in Paris Gordon’s repertoire is her so-called “perfect tank”; a tank top with built-in shapewear that helps boost the wearer’s confidence for the perfect fit. Paris Gordon’s tank top design is beloved in that it can be dressed up or dressed down, layered or worn on its own, and is truly a diverse piece for any woman’s wardrobe that’s made to be used again and again.



Nothing says outdoorsy clothing and sustainability quite like Patagonia, a California-based brand founded in 1973. Patagonia produces upscale pieces best for outdoors wear, with zip-up fleeces and breathable activewear bottoms among their top sellers. With an average price of about $200 for their warmer wear clothes, Patagonia’s prices are justified by their clothing’s durability and wearability. Patagonia also sells lightly-used and pre-loved items for a cheaper price both online and in-store, making for a budget-friendly and eco-friendly option. If you’re looking for everyday essentials in activewear, or timeless outerwear styles, head to Patagonia to see what this well-loved American fashion retailer has to offer.


Roundabout Designer Consignment

Established in 1989, Roundabout Resale Couture has made a real impression in America’s consignment community, and is now considered to be the country’s leading brand in luxury resale. Roundabout Resale Couture works both with individual sellers and directly with brands, giving them access to current and past designer collections at a great discounted value of up to 70%. They sell online, as well as at four in-store locations across New York and Connecticut. Name-brand becomes accessible when shopping at Roundabout Resale Couture, with selections from almost unlimited designers at a wide range of prices, dropping as low as $300 for pieces from Chanel, Gucci, and more. Skip the mall and shop small at Roundabout Resale Couture, and get ready to get your luxury on.


Savvy & Grace

Based and founded in Westport, Connecticut, Savvy & Grace offer unique pieces at attainable prices, from beloved luxury brands to quirky Westport themed knick-knacks and merchandise. Savvy & Grace offer mens and women’s clothing, jewelry, accessories and household items, at what they boast to be “better-than-internet” prices. With a well-lit and aesthetic interior, and free on-site gift wrapping, Savvy & Grace is a spot you’ll love to shop at — not just for the goods you purchase, but for the experience. Stop by Savvy & Grace for effortless styles that you won’t want to miss.


Scout & Molly’s

Scout & Molly’s Boutique is a brand based around comfortability and diversity in women’s styles, and they have been ever since their inception in 2002. With 20+ locations across the U.S., each boutique employs its own personal stylists for a wide range of styling and fitting needs. Scout & Molly’s niche is casual, fun clothing, with bright leggings and graphic tees lining the store’s shelves. With affordable prices averaging around $30 per item, Scout & Molly’s have gained a spot as a truly inclusive fashion retailer for thirty-something women looking to add a splash of color to their wardrobe.


Splash of Pink

Splash of Pink is Westport, Connecticut’s first and only Lilly Pulitzer Signature store, bringing floral prints, bright colors and one-of-a-kind designs to Fairfield County. Originally offering selections only for women’s and girls, Splash of Pink owners opened a Southern Tide shop next-door to expand their target audience to include men and boys, both online and in-person. Averaging at about $100 per piece, Splash of Pink’s styles are chic and vibrant, bringing upbeat and fun energy through their patterns and color palettes. For shoppers looking to fit in, while buying clothes that stand out, stop by Splash of Pink, where the modern day women’s fashion dreams come true.


South Moon Under

Founded in 1968 as Ocean City, Maryland’s signature small-town surf shop, South Moon Under has since evolved into an elevated shopping destination for men’s and women’s cool, effortless styles. South Moon Under’s expertly curated styles feature products from brands such as Free People, Levi’s and Dolce Vita. With styles that can be dressed up or dressed down, South Moon Under is a one-stop fashion destination when shopping for your upcoming vacation, a night on the town, or even for revamping your everyday wardrobe. Twenty-something men and women looking to feel high-end without breaking the bank: look no further than South Moon Under.



Launched in 2002 as a producer of premium tee shirts, Splendid has now expanded into a women’s and children’s lifestyle collection emphasizing comfort in clothing. With 15+ brick-and-mortar locations, as well as an online presence and collections in many large department stores, Splendid is a leading producer in simple styles that never disappoint. Casualwear and neutral colors make Splendid’s clothing appealing for many age groups, as they fit seamlessly into anyone’s wardrobe and everyone’s day-to-day routine. If you’re looking for comfortable and relaxed styles, with prices that won’t break the bank, Splendid is the place for you.



Talbot’s is a specialty American women’s fashion retailer, originally founded in 1947, and operating as a chain since 1973. Women aged 55 and older are the core demographic of Talbots, and though they have tried to expand their brand by marketing to younger women, these attempts have been relatively unsuccessful. Nonetheless, Talbot’s still thrives as a mature women’s retailer, with a wide assortment of tunics, tees, and trousers that are both timeless and classy. With clothing averaging at $100 per piece, these are pieces made to be reworn and treasured by women who see the value in quality clothing.



Contemporary fashion brand Theory was founded in New York in 1997, offering elegant men’s and women’s styles with materials that boost an impeccable fit. Theory’s brand boasts high quality pieces at affordable prices, although some might argue that their pieces are still far from budget-friendly, coming in at an average of $400 per item. The brand’s minimalist, luxury aesthetic attracts men and women who dress to impress, with blazers, shift dresses, and cashmere sweaters topping their bestsellers list. New York has certainly left its mark on Theory’s branding, and shoppers looking to emulate big-city styles will find much to love at Theory.


Urban Outfitters

Urban Outfitters is a lifestyle and fashion retailer with an emphasis on hip styles, cultural wellness and creativity. Founded in Pennsylvania in 1970, it has since expanded worldwide and operates under many different brands, such as Free People and Anthropologie. Stepping foot inside an Urban Outfitters store is all part of the brand’s aesthetic, from the vinyl collection to the recycled resale section: to shop at Urban Outfitters is just as trendy as their clothes are. Urban Outfitters is known for its eclectic assortment of home, fashion and wellness items, ensuring that your home is dressed just as well as you are. If you’re looking for quality denim, groovy patterns and a reworked vintage aesthetic, Urban Outfitters is the place to be.



Vince is the warm Los Angeles based fashion retailer that will leave you dreaming of California sunshine — known for understated luxury products with an elevated California aesthetic. Offering men’s and women’s lifestyle and fashion products, Vince pride themselves on offering modern-day, livable clothes while still remaining high-end. Vince’s products average at about $400 per piece, a price certainly justified by their quality materials and approachable luxury aesthetic. With retail stores across America and wholesale online globally, Vince is an enormous success for those looking to add a little luxury to their every day.


Vineyard Vines

Founded in 1998 in Martha’s Vineyard, a popular seasonal vacation destination, Vineyard Vines bring preppiness to the people with a recognizable pink whale and a plethora of collared shirts. Getting their start as a tie company, and later adding clothing collections for men, women and children, Vineyard Vines styles are the quintessential New England-esque clothing stop. With designs more commonplace than luxury, Vineyard Vines appeal to the everyday citizen who find themselves intimidated by high-end fashion but still want to make a statement in how they dress. Vineyard Vines most popular styles usually land in the $100 range, making them affordable without being cheap, and preppy without being designer.



West Coast aesthetic mixed with East Coast charm? You must be thinking about West, the Westport, Connecticut based lifestyle and clothing brand you won’t want to miss. Highlighting female fashion designers from around the world, West’s selection ranges from laidback graphic tees to pinstripe suits and boho-style tuxedo shirts. West also carries curated accessories and lifestyle items, from purses and hats, to mugs and beauty products, because your vibe is more than just what you’re wearing. With middle-aged women in mind, West has curated a perfect collection of everything a woman needs to make a statement while she shops.