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Annie O.
Pop into the Hotel on Rivington’s gift shop for a groovy mix of untouristy wares. Founded by a former publicist for Lou Reed and the Smashing Pumpkins, the glass jewel-box of a boutique proffers rockerish jewelry, vintage Rolexes, Shy cosmetics and Yosh perfumes. Don’t be intimidated by the myriad glass cases: The helpful staff will gladly let you try things on. 105 Rivington St between Essex and Ludlow Sts (212-475-3490)

BBlessing
Though this high-end men’s boutique has made a name for itself with its upscale streetwear, it offers a scattering of handsome tokens of affection, such as literary series 33⅓, which chronicles the making of albums by musicians like the Beach Boys and Nick Drake ($10–$11), private-label leather-bound journals with gilded edges ($65) and limited-edition boxes of chocolate ($30) from Swiss confectioner Alice (only 2,500 are made of each). 181 Orchard St at Stanton St (212-378-8005)

Doyle & Doyle
Operated by two sisters, this estate-jewelry boutique stocks vintage gems as well as a freshly minted private-label line. Give retro charms via cameo rings ($185), opal filigree brooches ($285) and diamond lockets ($150)—all discovered at flea markets and estate sales. 189 Orchard St between E Houston and Stanton Sts (212-677-9991)

Freemans Sporting Club
Just around the corner from Taavo Somer’s perennially popular restaurant, this clothing store–barbershop acts as a showroom for Somer’s natty menswear, cut from vintage dead-stock fabric. But the rustic spot also serves up an old-fashioned aesthetic via Le Chameau wellies for both genders ($400), Quoddy moccasins ($148–$220), culty Marvis toothpaste ($8–$12) and D.R. Harris shaving cream ($20–$36). 8 Rivington St between Bowery and Chrystie St (212-673-3209)

The Tenement Museum Store
Staying true to the LES’s colorful past, this quirky shop mixes Jewish, Irish and Italian goods with a sense of humor. Grab educational books like Yiddish with Dick & Jane ($15) and How the Irish Saved Civilization ($13), as well as photo mobiles ($13) and doormats that resemble manhole covers ($30). 108 Orchard St at Delancey St (212-982-8420)

Personalized gifts

Superdeluxe
Literally glowing (owners Adrienne Wong and Karin Spraggs used a broom to coat the ceiling with metallic paint), this jewel box of a space churns out some of the coolest custom stationery sets in the city, starting at $500. If you aren’t feeling quite that generous but want the illusion of personalization, most of the shop’s ready-to-buy stock—gold-edged decoupaged glass trays ($196), card sets ($8), pencil cups ($125) and paperweights ($65)—is embellished with subtly stamped initials. The duo also makes stunning silhouette portraits ($950–$2,100), which can ultimately be co-opted for custom stationery. 187 Chrystie St between Rivington and Stanton Sts (212-260-8300)

Anybody’s Custom Design Embroidery
Even though it’s tucked away on the second floor of the South Street Seaport mall—not exactly a destination frequented by NYC locals—this shop offers excellent, speedy service that could turn anyone into a monogramm addict. Choose from a slew of designs—cowboys, sports team mascots, flowers—and script styles, which they stitch, via in-store machines, onto the textile of your choice. We brought in a pair of Egyptian-cotton pillowcases snapped up from nearby Century 21 for $18—for $12, owner Max Louie embellished them with two sets of initials in Bridge Block, overnight. South Street Seaport, Pier 17, second floor (212-267-7070)