Montana Avenue (www.montanaave.com) is where affluent Santa Monica mothers—and increasingly, visitors—shop for themselves, their children, and their dogs. Boutiques have an airy, privileged bohemian vibe. Begin at the east end: The south side of Montana just west of 16th St. (1) Moondance Jewelry Gala (1530 Montana Ave.; tel. +1 310 395 5516; www.moondancejewelry.com) is a jewelry boutique that carries an impressive range of designer collections (not goods, but entire collections), with mother-daughter prices from $20 to over $1,000 (mom can stock up on serious jewelry, and her little girl can leave with something, too). Find rare, flawless stones, souvenirs, even jewelry trends (moonstone, turquoise, rose gold), and salespeople who are themselves budding designers.
Next door, to the left, is (2) Aura (1528 Montana Ave.; tel. +1 310 451 0181; www.aura-boutique.com), a spacious (1,500 square feet) store that personifies the uniqueness of Montana Ave. The boutique belongs to Kristin Tutor Eberts, a former set and costume designer. Her tastes run to formal gowns, like a beaded pale-blue Zac Posen dress that Sienna Miller wore to the Golden Globes, vintage scarves doubling as beach halters by Karen Zambos, and pricey, well-made jeans.
Traveling farther west, be sure to stop into (3) Kiehl's (1516 Montana Ave.; tel. +1 310 255 0055). Even if you're familiar with the old-fashioned drugstore-like ambience of this hair and skincare store from New York, you'll be impressed with the loft-like touches and extraordinary helpfulness of this L.A. outlet. Cross 15th Street and stop at (4) LF (1426 Montana Ave.; tel. + 1 310 458 2626; www.lfstores.com), crammed with pricey but unusual British fashions.
Walk a block to the (5) Aero Theater (1328 Montana Ave.), a working 1940s movie theater with a uniquely L.A. angle: showings of often old, sometimes rare films, followed by a Q&A with their makers. You can check the schedule and return for a later show.
Across the street, you'll find (6) Hey Kookla (1329 Montana Ave.; tel. +1 310 899 9499), which 20-something owner Alex Winston has stocked with tiny crystal necklaces (Adore by Natalie), ornate vegan handbags (Amy Kathryn), handpainted and handsewn "surfer chic" beachwear in soft prints (Aviator Nation)—all from local designers.
A few doors down, on the north side, you'll see (7) Every Picture Tells A Story (1311 Montana Ave.; tel. +1 310 451 2700; www.everypicture.com), a whimsical shop dedicated solely to children's story and picture books. If you're with kids, check the schedule for wonderfully animated readings.
Traveling farther west, cross the street to (8) Jeany (1302 Montana Ave.; tel. +1 310 255 0808), which expresses the Los Angeles obsession with jeans. You can find them in all colors (well, at least blue and white), cuts, and shapes, and the shop can further tailor the fit or embellish as you wish.
Continue west and cross Euclid (13th) St. to (9) Lucy (1230 Montana Ave.; tel. + 1 310 255 9994; www.lucy.com), stocking stylish active wear. The sock collection alone is marvelous. Across the street, the comfort vibe persists, with (10) Cozzi Cozzi (1231 Montana Ave.; tel. +1 310 260 5527), a tiny shop with a few rows of comfortable women's loungewear and beachwear.
Two blocks west, conclude your tour at (11) Father's Office (1018 Montana Ave.; tel. +1 310 393 2337), an upscale pub known for its blue-cheese-stuffed burgers, crisp herb-sprinkled sweet potato fries, friendly clientele, and 37 beers on a magnificent walled tap. Tip: Don't bother to line up where everyone else is; you can go directly to the bar and order your food and drink. Also go early (5 p.m.), or expect queues outside.
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