Federal
If your beau feels most at home with the antlers-and-Pendleton-blanket vibe, he’ll love Federal — a cozy-yet-hip spot specializing in all things heritage, rugged, and outdoorsy (or, at least, a cool city boy's idea of outdoorsy). A beard may not be required to shop here, but it certainly wouldn't hurt.
Where: 2216 14th Street NW; 202-518-3375.
Hugh & Crye
Men get just as frustrated by inconsistent sizing as women do, and having to spend extra cash on tailoring an off-the-rack shirt can be a bummer. If your guy is close to giving up on finding the perfect shirt, walk him down the stairs to this quiet and airy shop, where the staff will guide him through a modernized sizing system and help him find basics that work.
Where: 3212 O Street NW, Suite 5; 202-250-3807.
Lost Boys
Shop owner Kelly Muccio starts by stocking hard-to-find brands (Rogan, Band of Outsiders, Relwen) in her boutique, but goes above and beyond, to deliver serious customer service — from closet consultations to custom cocktails — that makes shoppers feel like members of an exclusive club.
Where: 1033 31st Street NW; 202-333-0093.
Suitsupply
This Dutch menswear brand supplies more than just suits, but the suits are the real draw. The new-to-Georgetown outpost offers traditional and modern styles in off-the-rack or made-to-measure options, at prices that start well below the typical mall chains. Should the fit need a little tweaking, customers can settle in for a coffee while the on-site tailor gets the job done.
Where: 2828 Pennsylvania Avenue NW; 202-800-7800.
Redeem
This boutique is co-ed, so ladies and gents can shop together for forward-thinking, slightly edgy clothing, shoes, and accessories. Think cool asymmetric cuts and moody color palettes that are more fitting for an art gallery than a boardroom. If your so-hip man-friend has ever pouted that he can only shop for clothes in New York, this is the place to bring him.
Where: 1734 14th Street NW; 202-332-7447.
Photos: Courtesy of Federal, Michael Andrews Bespoke, Alton Lane, and Redeem
Dr. K's Vintage
Most good vintage clothing shops will have a rack or two of men’s options off in the corner — but ask any vintage-loving D.C. man for his vendor of choice, and he'll send you to Dr. K (real name: Somkiet Umkerb). Among long racks packed with vintage concert tees, leather jackets, and military-issue gear, this is where your guy will pick up that perfect pair of broken-in boots or a just-right denim jacket.
Where: 1534 U Street NW; 240-888-6284.
Alton Lane
Let’s say your best guy is also something of a techie geek — how can you use this fact to get him excited about shopping for clothes? By sending him to Alton Lane, where he’ll be measured for bespoke suiting and shirts by a state-of-the-art 3-D body scanner. Should the airport-security element make him tense, the staff keeps customers’ preferred booze on hand to take the edge off.
Where:1506 19th Street NW, 3rd Floor; 202-232-2142.
Jack Spade
For casual clothes that aren’t boring (plus all the classic bags, preppy ties, and handmade-in-the-USA belts to go with them), this is just the spot. Fully decked out with interesting knickknacks, this inviting two-story boutique mimics the feel of a special vintage boutique much more than an established chain.
Where: 1250 Wisconsin Avenue NW; 202-333-1905.
GANT
Even if the phrase “unkempt sprezzatura” (the title of GANT's current lookbook) is a little too menswear blog-y for your boy, he's still likely to love this line of classic American sportswear. The new Georgetown store, set to open at the end of November, will offer all manner of Ivy League-inspired basics for work and weekend. And should your guy pick up a few super-soft oxford shirts from the Rugger line, prepare yourself for a strong temptation to “borrow” one for yourself.
Where: 3239 M Street NW; phone not yet available.
Michael Andrews Bespoke
Whether it's for a wedding, a formal event, or a new job, there comes a time when every man considers investing in a serious suit. When he's ready to make that commitment, the brand-new D.C. showroom for Michael Andrews Bespoke is your first stop. Inside this elegant townhouse-turned-menswear-haven, he can order a cocktail and discuss fit, fabric, and design with the experts, who will in turn help make his dream suit a reality.
Where: 1604 17th Street NW; 202-350-9001.
Photos: Courtesy of Dr. K's Vintage, Jack Spade, Lost Boys, Suitsupply