It can invigorate a company's image or squander its brand equity. To see which gambles paid off, Fortune turned to a few experts to judge some of the most dramatic transformations.
Apple - A Chic Redesign

Talk about a makeover.
Just imagine what an iBook or iPhone would look like with this
image on it: definitely not as chic.
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Ronald Wayne designed Apple's original logo in 1976 when the
company was still operating out of a garage.
It shows Isaac Newton sitting beneath a tree with an apple
dangling precariously above his head.
Rob Janoff used the same apple in his redesign a year later.
"You can almost feel the '70s and '80s taking place when you
take a look at that rainbow apple," says Bill Gardner, principal
of Gardner Design.
Apple dropped the multi-colored logo in 1998 for a monochromatic
version, produced in every color imaginable, until transitioning
it to today's popular shade of chrome.
BP - Re-Branding Faces Reality

After British Petroleum merged with Amoco, the oil giant
commissioned branding firm Landor & Associates and advertising
agency Oglivy & Mather to fashion a corporate identity that
would convey the image of a forward-thinking, socially conscious
company.
BP had already begun building that persona: After all, former
CEO Lord John Browne was the first oil executive to acknowledge
the threat of global warming.
The bursting green, yellow, and white Greek mythology-inspired
"Helios" symbol that replaced BP's shield is meant to imply a
shift toward alternative, environmentally-friendly sources of
energy like solar and biofuels, and relentless advertising has
made the company's initials synonymous with "beyond petroleum."
But a series of oil spills and accidents suggested that BP
wasn't walking the walk, leading some to consider its wildly
successful mark more a mask than its true face.
"If the story doesn't hold up, the mark and the brand start to
lose their luster," says Brendán Murphy, senior partner at
Lippinott, a brand management firm.
IBM - Simply Classic

In 1972, IBM ditched its original logo in favor of the symbol it has used ever since.
In an attempt to update its antiquated look -- the old logo
wrapped the words "International Business Machines" around an
image of the globe -- IBM tried two different block-letter logos
before legendary branding designer Paul Rand created the current
version.
In this modern design, the lines that make up the letters
represent "speed and dynamism," according to the company.
They owned the lines going through it before everyone started using lines," Gardner says. And because of its simplicity and originality, "you have a hard time desiring to mess with it."
Kraft Foods - Mismanaged and Indistinct

The association with fattening products like Kraft Macaroni &
Cheese -- and negative connotations stemming from its connection
to tobacco conglomerate Philip Morris -- tainted both Kraft's
corporate history and its logo. So it made sense that just under
two years after Altria (formerly Philip Morris) spun off shares
of Kraft to form a distinct company called Kraft Foods, the food
giant would want to revamp its image.
But it wasn't necessarily a success: While the slimmer styling
suggests healthier products, many analysts consider the new
logo, by Nitro design agency, a disaster. Introduced in
February, it's already been altered, with changes to both the
location and shape of the ambiguous "flavor burst," which evokes
both butterflies and flowers.
"I don't get a story from it," Belk says. "The fact that they
changed it twice in such a short period of time says that
they're not managing it very well. They're not taking a
strategic approach to it." What's more, the new logo bears an
uncanny resemblance to Yoplait's, which isn't even a Kraft
brand.
Procter & Gamble - No Devil Inside

The logo P&G used when it launched in 1851 pictured a man in the
moon with 13 stars, representing the original American colonies
-- à la the original U.S. flag. But critics later claimed the
stars connected to form "666" and that the curls were in the
shape of devilish sixes as well.
P&G chopped off the old man's bearded curls in 1991, and then
two years later, the company trashed the pictorial logo
altogether for the simple initials it uses today. "While it's
unfortunate that they had to change for the reasons they did,"
Murphy says, "I think the 'P&G' logo is a strong mark."
Starbucks - Song of the Siren

Here's one Starbucks concoction many hoped had disappeared a
long time ago. The brown logo featuring a nude siren had been
the company's icon since 1971, when it was developed by
Starbucks co-founder Terry Heckler.
In 1992, it was updated to the green logo used today, picturing
a less exposed siren. But in May of last year, the brown logo --
with the breasts covered -- made a comeback for several months
during a promotion. Even with the minor touch-up, the flashback
was not met with much enthusiasm.The retro logo "goes from
nostalgic to crude," says Belk, whose opinion was shared by
many.
UPS - Modern and Traditional

In 2003, as UPS moved into the digital age -- from packaging and
shipping to managing logistics, too -- the company outgrew its
42-year-old iconic logo. Celebrated in the design community for
its connection to legendary designer Rand, the original logo and
its old-fashioned bow gestured to the company's roots in
neighborhood package delivery. "It had a humor and a humanity to
it," Murphy says.
But the new logo represents a strategic decision to emphasize
UPS's expanded business operations, and analysts also praised
the company's FutureBrand designers for nodding to UPS's
heritage by preserving the shield, keeping it lighthearted, and
leveraging the color brown. "You would never think [brown] would
be an asset," Belk says, "but in their case, it is."
Wal-Mart - Softening Its Image

Wal-Mart didn't always make its employees as smiley as the happy
face that rolled back prices on its commercials. "They were
known as a heartless, soulless company that didn't care about
people -- even their own people," Belk says.
But Wal-Mart's 2008 branding makeover by Lippicott produced a
logo that now conjures up the image of an "inviting and
accessible" store, explains Belk, rather than the "daunting and
monolithic" one the old logo (in use since 1992) projected.
The redesign transformed the big-box store's name to one word,
used standard capitalization and a softer shade of blue, and
added a yellow spark symbol. The new logo, like the company's
updated tagline -- "Save Money. Live Better." -- invigorates the
company with an "altruistic mission," says Belk, as it expands
its reach from rural America to an urban consumer.
Xerox - X Misses the Spot

;It's so painful for me to even look at that thing," says
Gardner about Xerox's new logo, which the company unveiled last
year. Xerox decided to lose its signature 'X' logo in hopes of
changing its reputation for being just a copier and printing
company as it increases its focus on software and services.
But analysts and customers have been critical of the redesign --
Xerox's biggest makeover in forty years. "The new logo is first
and foremost a sphere...and the less obvious 'X' is almost an
afterthought," says Gardner. "Xerox owns the letter 'X' in the
corporate world. Why would they want to bury the 'X' instead of
making the most of it?"
The company stands behind its decision, however, saying in a
press release that the new look is "more lively" and the 'X' in
the ball represents the company's connections to customers,
partners, industry and innovation.