Men's Shopping Guide

23 Fairfield County men's stores to know

Fairfield County abounds in fantastic shopping options for the man about town, from Greenwich to New Canaan, Westport, Fairfield and beyond. Each store listed has its own vibe, different items and brands, not to mention diverse styles/looks, on offer. Below is a short list to help you in your search for the clothes that suit you best.

Allen Edmonds


One of the great American heritage brands, AE offers fine shoes at all price points, as well as attentive service and a vast swath of—dare I say it?—haberdashery. Since diversifying from footwear and leather goods into jackets, clothes and beyond, the already fine shoe mecca has become a menswear cornucopia.

Banana Republic

Westport | Fairfield | Stamford

Banana Republic is a tick up from the Gap, in terms of quality in most people’s eyes, but the brand is affiliated with Old Navy and Gap. Here, you will also find all you could want, from belts, socks, shirts, jackets, shoes to sweaters, coats and watches, all at decent prices points. Like J.Crew, it’s one-stop shopping, and pants abound! (I go for their Merona wool V-neck sweaters.)

Brooks Brothers

Westport | Greenwich

BB = God’s plenty, in terms of a man’s clothing needs: from mere collar stays to the Golden Fleece line of suits. The staff is uniformly knowledgeable; and the newer Red Fleece line now helps out younger gents; Black Fleece, for those looking to dress NYC-chic, is Thom Browne-designed; and everything in between just works. The many shops in the area, whether you want repp ties or a pair of summer bucks, are staples.



If you need chic, luxe denim, a knit puffer vest, or an English-collared check-print shirt and a pair of gleaming cufflinks to go with the leather accessories and polo gear you’re craving, Casablanca is essential one-stop shopping—and a must. But while geared toward the “horsey” set, its brand emblem also adorns simple, superb T-shirts knit caps, finely woven sweaters, and a series of accessories that are bright, elegant and classic.

Darien Sport Shop


Darien Sport Shop

The shop (with the big D visible from Route 1), carries ALL the brands, from upmarket (Peter Millar) and trendily preppy (Vineyard Vines) to casual chic (Tommy Bahama), along with slews of accessories, including caps, bags and blazers. Great service here, too.


Ed Tunick


Personalized shopping is the name of the game here: Tuxedos are generally the main draw, as well as duds for the big and tall set, and ties, blazers and the like. The shop has been in Fairfield County for nearly 40 years—not a chain, but one of a kind.

Family Britches

New Canaan

Family Britches New Canaan

Starting with jeans and tops long ago, this family biz moved to a brick-and-mortar in New Canaan, and will accouter you very well in the most elegant attire: Their “invisible valet” service alone is noteworthy—and worth taking advantage of!



With the emblematic “H”-buckled belts, majestic neckties, bags, and they even have the blankets (you don’t have to order them online anymore!), Hermés provides all the mystique of Parisian couture mingled with the superlative looks and the fine art of fabrics exceedingly well-cut and designed. Watches, accessories and those gorgeous orange-aureate boxes and carrier bags are there, too. Yum.

Island Outfitters

New Canaan | Fairfield

Island Outfitters Fairfield

With preppy, beachy, New Englandy yacht looks (Newport, Cape Cod), from hats to key fobs (including custom-wear), Island Outfitters makes you look like you’ve been lounging waterside or boating. Not a bad way to be, especially if you’re summering at the Vineyard.

Jack Spade

New Canaan

Jack Spade

Kate Spade’s “male counterpart” is bold, chic, dapper and fun. From messenger bags to argyle socks and superb ties/accessories, you can’t go wrong with Warren Street’s line of menswear, which offers kewl kids and guys streetwear and goods to also make it on Wall Street. The shops themselves sport some of the best interior design around.



Westport | Greenwich | New Canaan

J.Crew revamped years ago, licensing with heritage brands such as Alden (for shoes), and opening wonderful brick-and-mortars everywhere, with the whole shebang in styles, from socks to belts to the now-standard Ludlow line of suits and separates. What separates J.Crew itself is its cultivation of true preppy chic, which you makes you look more chic than the usual preppy.


Contact Susan Kantor for an appointment - Phone: (203) 246-0403

J Hilburn

Custom clothing, particularly shirting, is what Fairfield’s J.Hilburn does—though there is also a ready-to-wear collection. A stylist will help you look your best, and also, teach you how to dress your best (what more could one ask for?)…

Johnston & Murphy


The cut on J&M jackets is superb, and the elements are wonderful: they often have functional buttons to go with surprisingly daring styling. The brand offers everything: sturdy shoes (from crepe soles to dress brogues), as well as accessories (scarves, cufflinks, gloves, socks), pitched somewhere between Banana Republic and Brooks Brothers. They also have casual clothes that transition well from work to evening, and their outerwear especially includes functional elements that are also highly stylized and make a statement.



Men's Shopping Guide

The crocodile came back to the fore some time ago, and the stores offer bags with the iconic emblem, as well as sweaters, T’s, hats and the original, famous cotton pique polo—the first of its kind in history, invented by French tennis legend René Lacoste (who also invented the automatic tennis service machine).


Westport | Greenwich

Known primarily for its denim, Lucky Brand also has its own line of stylish shirts, shoes and accessories growing in popularity. The jeans, however, are the real draw: Lucky’s many cuts will put you nicely in any kind of denim, from heavy or distressed, in skinny to boot cut or relaxed, most with “alligator bites.”

Mitchells & Richards

Westport (Mitchells) | Greenwich (Richards)

Richards Greenwich

These upscale emporia stylishly outfit you in all the most illustrious brands, with everything you need (think shoes to scarves). Choose from Armani, Canali, Hermés, Isaia and Zegna (photo above: Richards), to name a few, along with others at lower price points (note: the experienced on-site tailor will give your garment supreme fit, too). The staff is superb; the array of clothes is ultra-fine; and you will uncover luxury galore.


Westport | Greenwich

EVERYONE wants Patagonia. It’s like the new North Face but from…Patagonia. Whether it’s a puffy jacket or simply outerwear for the outdoors, which is what this brand and its unusually incredibly nifty shops (the Westport spot is dizzying) specialize in, your kids (and you) will find it perfectly perfect.


Ralph Lauren

Greenwich | New Canaan

Ralph Lauren New Canaan

RL means American heritage, across its incredibly eclectic but unmistakable b(r)andwidth, from Polo to Purple Label, with jackets, trousers, suits, shirts and more. Staff will help lead you precisely to what suits you (literally), as there’s everything here a man could want and more, depending on your style.

Steven Alan

Westport | Greenwich

Steven Alan Westport

Steven Alan sources from hip designers, and though the looks are a bit similar to Theory (see below), SA has everything from shirting to sunglasses with collegiate kewl goods and hip prints (madras is in, especially). I like their boxers and lounge pants, personally.


Westport | Greenwich

Theory cuts streamlined, slim and chic designer-wear made for fashion horses who want to look en vogue, au courant and fit their slender frames to sharp lines that enhance and highlight them—whether the wearers are men or women.



Vilebrequin Greenwich

Hitting the beach? Wanna be chic ’n’ sporty or dapperly done up for your sporting activity? Look no further: swimwear, flip flops, resort wear (I LOVE that) is at Vilebregquin, and fitted casual wear for all occasions will make it seem like you are off to San Tropez (or just came back).



Vince is really tailor-made for the hip (and the hipster, as well), with lines of cold-weather clothes that go with more casual, warm-weather henleys, pocket T’s and slim-cut looks, in trousers and (light or heavier) sweaters. For the youthful, and those wanting to look it, too.

Vineyard Vines

Westport | Greenwich | New Canaan

Vineyard Vines Greenwich Ct

VV: think true preppy chic, though it all began rather simply with nifty, distinctly playful patterned (and unmistakable) ties. Since then, the iconic whale emblem has become as omnipresent on madras shirts, khakis and fine casual/dress apparel as Lacoste’s crocodile.





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