Watching the first half of “Alfie” is like flipping through the Christmas issue of Vogue. The cast is beautiful, the clothes and apartments are stylish and classy, and the shallow plot unfolds in a glamorized New York City covered in sparkling, powdery snow. Like the fashion magazine, the first part of the movie is entertaining in a deliciously mindless way. Sadly, its second half reaches for greater depths but falls embarrassingly short.

As an impeccably dressed limousine driver, Alfie (Jude Law) glides around the city seducing beautiful women while eschewing any form of commitment. His carefree, obnoxious attitude is at once endearing and infuriating, to both his conquests and to the film’s viewers.

Alfie’s womanizing ways, which should disgust, are at least temporarily forgivable when he smiles charmingly at the camera. The character’s ability to gain our sympathy is entirely because of Law’s acting, and it is to his credit that he doesn’t rely solely on his good looks to win the audience.

On the other hand, the script — rife with cliches — is no help in eliciting the audience’s emotional connection with the main character.

The original version of “Alfie,” a classic of the ’60s, stars Michael Caine in a London crawling with male chauvinists. Back then, the tale of a womanizer who was led to question his lifestyle was fresh and sharp. However, almost four decades later, the story of the carefree bad boy who grows lonely and searches for love is a tired one. And in this era of “Sex and the City,” it’s hard to believe that the strong and intelligent women in “Alfie” would put up with so much.

Alfie’s life, as he tells us, revolves around “wine, women and — well, actually that’s it.” In the movie’s 106 minutes, Alfie’s conquests include a married woman (Jane Krakowski), his best friend’s ex-girlfriend (Nia Long), a single mother (Marisa Tomei), a mentally unstable party girl (Sienna Miller) and a woman at least 20 years his senior (Susan Sarandon).

The women all give excellent performances, and their multi-dimensional characters add warmth to an otherwise cold film. Long is vulnerable and strong as Lonette, a well-intentioned waitress whose life is haunted by one foolish night with Alfie. It is the affair’s repercussions that eventually awaken him to the pain his carefree lifestyle causes others, and ultimately himself.

Miller, Law’s off-screen girlfriend (for now), is captivating as a broken beauty. The Alfie-in-love montage of the two parading around the New York social scene during the Christmas season is pure fashion photography. As a couple, they seem too physically perfect to be real.

In the film’s most interesting and multi-layered role, Sarandon intrigues Alfie as an older, female version of himself. It’s satisfying to see the character in a relationship where the woman is clearly in control.

Sarandon maintains a seductive aura of mystery, even as Alfie starts to grow attached to her. Her iciness cuts through his chauvinism to give the movie a twist of feminist strength.

Unfortunately, the movie departs from its light, breezy tone about halfway through, instead attempting to explore the meaning of life and love. At the film’s end, he looks quiveringly into the camera and asks: “What’s it all about?” The moment encapsulates everything wrong with “Alfie” — blatant cliches, sophomoric deepness — and leaves an atrocious final impression.

The film’s second half is also irritatingly repetitive and anti-climactic. As he falls into a rough patch of bad luck, Alfie has the epiphany that his swinger lifestyle could leave him alone and miserable. Seemingly reformed, he returns to one of his women (we’re left in suspense about which one) to woo her back — only to fail, have another epiphany, and try another woman.

By the end of the film, the audience couldn’t care less about Alfie, whose self-pity becomes exasperating. Law is much more effective early in the movie, but by the end his obnoxious charm is entirely depleted.

At its best, “Alfie” is entertaining, albeit shallowly. At its worst — especially when it ponders questions beyond its grasp — the film is a miserable failure.