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Men's Shopping Guide

23 Fairfield County men's stores to know

(page 1 of 4)

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.

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