Best Men's Clothing in Boston

2015 Best Men's Clothing, Accessories

Ball and Buck

Boston

With deer heads mounted on the wall and a stack of vintage Playboys for sale, Ball and Buck is a refuge for every red-meat-eating, style-conscious male tired of the same…Read More

2015 Best Men's Clothing, Casual

Sault New England

Boston

Owner Philip Saul (pictured) will bring sartorially salty New England cred to your closet. Pick up a button-down, available in a variety of fabrics, from the store’s eponymous label, made…Read More

2015 Best Men's Clothing, Fine

J. Press

Cambridge

In a world where trends change daily, this preppy haberdashery recalls the proper Harvard Square of yore. Looking to impress in the boardroom? Try the U.S.-made “Super 120S Wool” charcoal…Read More

2014 Best Men's Clothing, Casual

Caramelo Clothing Company

Jamaica Plain

Know a guy in need of a makeover? Steer him to this fledgling family-run menswear spot, where the eclectic threads have personality, like the flower-printed Original Penguin button-downs; slim-fit Levi’s…Read More

2014 Best Men's Clothing, Fine

Louis

Boston

Originally established as a fine menswear store, this Boston institution is now run by fourth-generation purveyor Debi Greenberg, who continues the family tradition by offering made-to-measure suits, ties, and shoes…Read More

2014 Best Men's Clothing, Accessories

Ball & Buck

Boston

Mark Bollman’s shop may be hard to spot (the entrance is on a side street), but a trip here is a must for dapper gents with an outdoorsy streak. The…Read More

2013 Best Men's Clothing

Uniform

Boston

This was a winner in our 2013 Best of Boston Readers’ Poll. See all the 2013 winners…Read MoreRead More

2013 Best Men's Clothing, Dressy

Louis

Boston

Louis’s long, storied history has given it a certain cache in the local and national fashion worlds, but this isn’t a place to rest on its laurels. To see how…Read More

2013 Best Men's Clothing, Casual

Uniform

Boston

A small but well-thought-out selection of hats, bags, bathing suits, shirts, and pants from brands both familiar (Levi’s) and niche (the U.K.-bred collection Brixton) means that even if you don’t…Read More

2013 Best Men's Clothing, Accessories

Bobby from Boston

Boston

Anatomy of a Winner:
Imagine raiding the closet of a well-dressed uncle, whose discarded college wardrobe has only grown more stylish with age. That, in essence, is what it’s like to…Read More

2013 Best Men's Clothing, North

John Farley Clothiers

Newburyport

Located just a block from Newburyport harbor, John Farley Clothiers has been a fixture on the North Shore for decades, and for good reason: It offers everything from tailored clothing…Read More

2013 Best Men's Clothing, West

Mr. Sid

Newton Centre

Is there anything out there more wonderfully old-school than Mr. Sid? The parquet floors; the in-house bar, hair salon, and billiards table; the genteel service—it all feels reminiscent of another…Read More

2013 Best Men's Clothing, South

Natale’s

Norwell

Natale’s is the place to go for high-end men’s clothing south of the city. Everything in the store is tailor-made with only the finest wools and fabrics; staffers pride themselves…Read More

2012 Best Men's Clothing, South

Natale’s

Hanover

The store’s namesake, Natale Agostino, passed away in 2011, but his son Carlo has kept this Hanover landmark in top shape. The shop’s own brand of suits, slacks, and other…Read More

2012 Best Men's Clothing, North

Giblees

Danvers

Occupying the better part of a nondescript strip mall on Route 114, Giblees has attire for every manly occasion: golf, work, weekends, and formal affairs—plus a pool table and coffee…Read More

2012 Best Men's Clothing, Casual

Uniform

Boston

A memo to all men: Enough with the cargo shorts and polos, already. This South End shop offers a mix of well-known men’s brands (Ben Sherman) and smaller, fashionable lines…Read More

2012 Best Men's Clothing, South

Natale’s

Hanover

The store’s namesake, Natale Agostino, passed away in 2011, but his son Carlo has kept this Hanover landmark in top shape. The shop’s own brand of suits, slacks, and other…Read More

2012 Best Men's Clothing, Suburban

Mr. Sid

Newton Centre

2012 Best Men's Clothing, Dressy

Drinkwater’s

Cambridge

Discover your inner Don Draper with Italian wool jackets, made-to-measure shirts (including sharp styles from Engineered Garments), and elegant ties…Read More

2012 Best Men's Clothing, Fitness

City Sports

Boston

Whatever your passion—volleyball, basketball, yoga, even bocce—City Sports has the gear you need, including high-performance pieces from its in-house CS line. Ask one of the sporty employees to help you…Read More

2012 Best Men's Clothing, Accessories

Bobby from Boston

Boston

Whether you’re shopping for a special occasion or just looking to jazz up your business attire, there’s no place better than this South End vintage shop, where owner Bobby Garnett…Read More

2012 Best Men's Clothing, Accessories

Drinkwater’s

Cambridge

Discover your inner Don Draper with Italian wool jackets, made-to-measure shirts (including sharp styles from Engineered Garments), and elegant ties…Read More

2012 Best Men's Clothing, West

Mr. Sid

Newton Centre

2011 Best Men's Clothing, West

Mr. Sid

Newton Centre

Gents who prize efficiency won’t find a better place to shop than Mr. Sid, which stocks an impressive selection of high-end brands, employs a fleet of tailors and barbers, and…Read More

2011 Best Men's Clothing, South

Natale’s

Hanover

Forget flashy labels or flimsy Men’s Wearhouse offerings. You’re guaranteed to find a better fit—not to mention great service—at this father-and-son-run spot. Italian-born owner Natale Agostino began as a tailor’s…Read More

2011 Best Men's Clothing, One-Stop Shopping

Barneys New York

Boston

Your credit card may get a workout here, but think of the time you’ll save: an entire wardrobe in one fell swipe. Workdays are covered with Surface to Air button-downs…Read More

2011 Best Men's Clothing, North

Peter Mark

Newburyport

Owners Peter and Cindy Murphy continue to impress with an impeccable yet not-too-stuffy selection. Snag a few Robert Graham button-downs and coordinating ties to outfit him during the week, and…Read More

2011 Best Men's Clothing, South

Natale’s

Hanover

Forget flashy labels or flimsy Men’s Wearhouse offerings. You’re guaranteed to find a better fit—not to mention great service—at this father-and-son-run spot. Italian-born owner Natale Agostino began as a tailor’s…Read More

2011 Best Men's Clothing, Casual

Uniform

Boston

Owner Gary Ritacco and the rest of the gang at Uniform have both a superb eye for quality brands (think Trovata and Life After Denim) and a rebel’s sense of…Read More

2011 Best Men's Clothing, West

Mr. Sid

Newton Centre

Gents who prize efficiency won’t find a better place to shop than Mr. Sid, which stocks an impressive selection of high-end brands, employs a fleet of tailors and barbers, and…Read More

2011 Best Men's Clothing, Store for the Rest of Us

Bloomingdale’s

Chestnut Hill

Outfitting your postmarital life is no small feat, so finding everything you need in one place and getting sage advice certainly helps. Bloomie’s consultants deftly provide estimates and mix-and-match services…Read More

2011 Best Men's Clothing, Sophisticated

Alan Bilzerian

Boston

Economic downturn bedamned. This boutique is still standing tall, thanks to a rocking inventory that keeps the well-heeled masses coming. Find handmade Chelsea boots by Albert Fasciani, a one-of-a-kind Imp…Read More

2010 Best Men's Clothing, Sophisticated

Barneys New York

Boston

The Brooks Brothers non-iron shirt has its place, but when the situation calls for something a little more snazzy, the best-dressed men in town head to Barneys. The men’s department…Read More

2010 Best Men's Clothing, Casual

Uncle Pete’s

Boston

A welcome addition to gifty, girly Beacon Hill, this new boutique is as hip as it is friendly. On any given day, you’ll find Uncle Pete’s proprietor Peter Tam chatting…Read More

2009 Best Men's Clothing, Upscale

Alan Bilzerian

Boston

Nearly three decades on, Alan Bilzerian’s trailblazer status remains unchallenged. It’s the go-to for avant-garde imports like Rick Owens and Yohji Yamamoto, as well as for the keen advice from…Read More

2009 Best Men's Clothing, Casual

Uniform

Boston

Not feeling up to excessive sartorial risk-taking? That doesn’t make it okay to fall back into the Gap (you’ve come too far!). More moderately priced than Barneys, less alternative than…Read More

2008 Best Men's Clothing, Accessories

Drinkwater’s

Cambridge

Many men’s boutiques seem to have forgotten the importance of details: Like, where’s a guy supposed to get a decent pair of dress socks in this town? (SmartWools don’t count.)…Read More

2008 Best Men's Clothing, West

Mr. Sid

Newton Centre

In the 21st century, Boston’s been getting used to the idea of dynasties, what with the Red Sox winning two World Series championships and the Patriots a trio of Super…Read More

2008 Best Men's Clothing, South

Natale’s

Hanover

If The Thomas Crown Affair—vintage McQueen version, please—taught us anything, it’s that there’s no better sandpaper for a man’s image than a tailored wardrobe. That kind of polish is stock-in-trade…Read More

2008 Best Men's Clothing, Casual

Stel’s

Boston

Stel’s deserves this honor if for no other reason than it introduced Boston to New York’s Seize sur Vingt. The designer’s crisp, colorful dress shirts work as well with jeans…Read More

2008 Best Men's Clothing, North

Peter Mark

Newburyport

While the Metrosexual dithered over exfoliants and the GQ Dandy sweated his tie width, a new male animal was emerging from the sartorial ooze. Or so declared the Times of…Read More

2008 Best Men's Clothing, Sophisticated

Louis Boston

Boston

Hey, you—in the cargo pants and Chucks. Casualwear is fine for casual moments, but your big client meeting, your anniversary dinner, and for-the-love-of-Christ your best friend’s wedding call for something…Read More

2007 Best Men's Clothing, West

Mr. Sid

Newton Centre

It must be that a parallel universe exists in Newton Centre, where for 40 years Mr. Sid has managed to make men’s shopping a social activity. Could it have something…Read More

2007 Best Men's Clothing, North

Peter Mark

Newburyport

This is a shop that understands there’s more to the male wardrobe than suits and ties. Here you’ll find shelves piled high with weathered tees by Jake Agave and long-sleeve…Read More

2007 Best Men's Clothing, South

Natale’s

Hanover

Your ill-fitting warehouse suits and casual-Friday carpenter jeans are getting you nowhere fast, mister. Time to pay a visit to Italian-born custom tailor Natale Agostino, who’s schooled in the ways…Read More

2007 Best Men's Clothing, Casual

Uniform

Boston

Saturday afternoon. T minus two hours. Sure, there was chemistry in your e-mail exchanges, but now your blind date is about to size you up in person. The team at…Read More

2007 Best Men's Clothing, Dressy

Barneys New York

Boston

You wonder how some guys look so damn sharp all the time? We’re betting it’s the Barneys men’s department. All the key pieces are in place here: suits, shirts, ties,…Read More

2005 Best Men's Clothing, Nantucket

Murray’s Toggery Shop

Nantucket

No prepster would be caught dead without a pair of Nantucket reds, and Murray’s happily sells pair after pair of the pinkish shorts and slacks to covetous customers. The other…Read More

2005 Best Men's Clothing, Berkshires

Steven Valenti Clothing for Men

Pittsfield

So many men’s stores have forsaken good, old-fashioned service for the ubiquitous bottom line. But integrity still means something at this North Street shop, where customers can choose from among…Read More

2005 Best Men's Clothing, West

Mr. Sid

Newton Centre

When it comes to clothes, most men could use a little help. Thankfully, the enormous Mr. Sid carries all the hottest fashions—casual Zegna-Sport, formal Brioni, and classic Bruno Magli—and employs…Read More

Most Viewed Winners of Shopping

  • Brookline Booksmith, 2015 Best Bookstore
  • Alan Bilzerian, 2015 Best Men's Shoes
  • Mahoney’s Garden Center, 2015 Best Garden Supplies

Most Viewed Winners

  • Neptune Oyster, 2015 Best Seafood Restaurant
  • Ostra, 2014 Best Seafood Restaurant
  • La Morra, 2015 Best Italian Restaurant