Jessica Simpson presents a style conundrum. When she's on, she is on. But when she has a fashion blunder, it's bad enough to make national news.

She has some serious strengths and heads a massive fashion empire that includes clothes, handbags and shoes -- but one might wonder how it can be worth $100 million when Jessica herself can't consistently dress herself well.

The singer/actress/designer is rumored to be pregnant again, despite having just birthed daughter Maxwell Drew in May. Hopefully, her maternity looks this time around will set some new trends -- because Simpson does know how to pull an outfit together.

For example, this black pantsuit (from 2010) could be too "ladies who lunch" in lesser hands, but that bouffant hairdo gives it a Brigitte Bardot vibe.

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But sometimes her looks are "almost but not quite" right. This nude-colored gown might hug her curves, but the piping and halter neckline are unflattering. And what's with the Lucite stripper heels?

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We do give her props for having great hair. Yeah, it's big, but she's from Texas -- so it's pretty tame by those standards.

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She also isn't afraid to play with trends, even if only for a day or a few weeks, like this white blonde bob from 2006, paired with a pretty purple dress and slouchy brown boots. This ensemble would still work today.

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What's Right:

LBDs are her domain. This one looks great on her, since she lets her hair be the main accessory.

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She also sparkled during her first pregnancy. Even though she was about to pop, she didn't sacrifice one iota of style (or apparently a single sequin).

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Simpson also does retro well. This perfectly paired red and white ensemble from 2006 is one of her prettiest, most delicate looks. She effectively channeled both Marilyn Monroe and Jean Harlow.

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Simpson can accessorize like nobody's business, so it's no accident that her clothing empire rakes in millions. She knows her way around an oversized bag and a pair of killer heels, be it stilettos or boots.

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In 2005, she took a simple black ensemble with a longer length leather skirt and turned it up a notch with all the gold chains. It might be a bit too much on a novice fashionista, but on her, it worked.

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J. Simps doesn't fear casual, either. She wears jeans - forget skinnies, she's a flared-leg, bootcut devotee - and keeps the entirety of the look voluminous.

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She's also a risk-taker who isn't afraid of unforgiving jumpsuits with long pants. It's chic because it's black, simple, and wearable.

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Simpson works the shorts variety, too, which is cute and summery. It was age-appropriate for her back in 2006, but not so much today.

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What's Wrong:

Bigger is better in Texas. Simpson's big curls, big and bold gold outfit and her big boobies scream "I worked the beauty pageant circuit." This is not the gilded age, girl.

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The checked, sky blue dress she wore in 2010 was ill-fitting, and the fabric didn't lay flat. For a curvy girl, that's problematic.

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In 2003, she wasn't as stylish. But the Texas girl still wears boots -- even though her style profile has improved.

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There's a little too much volume here, too.

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And here. The fabric overwhelms her.

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How to Fix It:

A mom with a fashion empire needs to stay far, far away from boobie-baring outfits like this. Those things aren't the same size nor - despite her claims to the contrary - do they seem real. No breast is that round or that high up on the torso.

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Also, we'd recommend less of the mall-chic outfits, like this over-designed black frock from 2005.

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Simpson should always go with more of these short, sexy, classic ensembles. The white lace pops against her tawny, glowing skin (another Simpson signature) and the updo is as chic as it gets. It's mod done right.

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Simpson also admitted to getting lip fillers in the '00s, which gave her that weird "trout pout" effect so popular among starlets these days. She should keep her kisser natural, glazed with gloss, not plumped via injectibles.

We also like this hairstyle on her because she toes the line but doesn't cross over into "too much" territory. We love that she takes risks and tries new things, but she can really work the blonde bombshell thing if she sticks to what she does best.

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