Alyssa Milano is 40 and the mom to a young toddler -- son Milo -- but she still emits a youthful, effervescent glow. She's naturally pretty and in possession of a dynamite smile, and her style remains enviable.

Milano has her foot in the fashion world, as she designs sports apparel for women. Her Touch range allows female sports fans to proudly sport the logos of their favorite teams in form-fitting tops, so they don't have to sacrifice style to show their fandom.

So she knows what looks good on a woman's body and what doesn't...

...like this nude, past-the-knee column sheath, which hugged her petite figure. She accessorized flawlessly with a chunky necklace and one wristful of bracelets.

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That said, she's not above some questionable fashion choices, like this black pantsuit with a starburst bodice and bright, bold heels. It's a tall girl's ensemble, even though we applaud Milano for her fashion forwardness.

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What's Right:

This outfit is deceptively simple. It's actually quite fashion forward, mixing a black and white flannel with leather leggings and bright orange heels. Kudos for Milano for putting this snappy of a look together.

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The ultimate in mom chic! This flirty, striped RVN dress is playful, wearable and fashionable. Milano is living proof that moms can look faboosh! Her best accessory is lil' Milo.

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Another winning combo is her frilly, school marm-like cream sheer blouse paired with a tough but twirly leather skirt with a major modern touch in the form of pockets. The result is chic and sexy.

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Again, we're loving the actress' daring embrace of color. The bright green, sleeveless dress and melon shoes are so darling.

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What's Wrong:

This white Emilio Pucci pantsuit was too Las Vegas matron for Milano. The see-through, billowy, flared pants... the everything. This was an epic fail. Sorry.

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This black dress might have been on the other side of this list if the sheer top didn't flatten and crush her boobies. It looks ill-fitting.

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There's too much accenting here, from the leather belt, to the ruffly strap to the high-low hem to the thick black and white zebra stripping. It widens her petite frame in an unflattering way. The high-low hem is not making a comeback for the new season, BTW.

Michael Loccisano, Getty Images

How to Fix It:

Milano's pairings tend to be cute, colorful and slightly daring. This ensemble of a loose, turquoise blouse and bone-colored shorts are sweet and chic on her. The color and the strappy shoes help her pull this off. She needs to continue to go this route.

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An LBD is an LBD. But Milano's terrific figure and legs are spotlighted here in this ruched frock. As long as she pairs her LBDs with that dynamite smile, we will remain interested in her look and her style.

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This lacy, peek-a-boo Lorry Newhouse dress could push Milano to worst dressed lists. But for some reason, she carries it with confidence.

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Milano doesn't often hit glam and black-tie red carpets, but when she does, she wins! This tangerine Ports 1961 dress grew on us. We did not love it at first, but the belting, the pleating and the coloring were all right when considering the overall context of her personal smile. Alyssa Milano does not fear color, and it totally works for her.

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