Pop singer-turned-business woman Jessica Simpson is one successful (and rich) lady. She is a true beauty who's business-savvy, a doting mom of two adorable cuties, a loving wife to her hunky hubby, and an all-around fun-to-follow popular celeb. Jessica has been in countless photos over the years ever since she first came on the scene, and as she has changed her look to some degree over time, it is always fun to see her photos on the web, in magazines, and on billboards.
Since Jessica is such a beautiful woman, most pics of her turn out wonderfully. She looks like that girl-next-door everyone wishes they had, with an all-American touch of down-to-earth sweetness paired with an irresistible splash of sexiness. She’s got all the assets a girl could hope for and a guy would want to look at. From the bouncy blonde hair on her head to her well-heeled and pedicured feet, this stunner is a knockout… most of the time.
Because nobody’s perfect, Jessica can’t always be flawless. Sometimes, a photo of the star is put out there that isn’t the most flattering. Perhaps it is the fault of the photographer or maybe Jessica was having a bad day, but there are some pics of the celeb that don’t capture her best moments. That said, these “bad” pics are still better than most people’s best!
Here are some pics of Jessica that are smokin’ hot and others that are just not. Do you agree with our classifications? Can Jessica do no wrong in your eyes or does she sometimes miss the mark? You be the judge.
15 Sultry Simpson – Hot
That look in Jessica’s eyes is so captivating that it should be illegal! This chick knows how to work the camera with a look that could burn a hole right through the lens. Her super-sexy hairdo and stunning smoky makeup make Jessica even more alluring than she already is, and her hand placement is perfect for this come-hither look. Even some of the most famous models in the world don’t have a face as fine as Jessica’s. She surely hit the genetic jackpot, and this photo emphasizes that fact to a tee. Her glossy lips and flawless skin are hard to turn away from, but the good thing is that you don’t have to! What a beautiful pic of this glamorous gal. A vote for “hot” doesn’t even do her justice!
14 Barefaced Babe – Hot
Who else do you know that looks so darn pretty with absolutely no makeup and a simple hairstyle? Jessica is surely a natural beauty and this 100% barefaced photo shows us that she is not afraid to show off her “Plain Jane” side. Her warm chocolate brown eyes and smooth, supple skin are impeccable, and those rosy pink lips make for the perfect pout. It is really nice to see Jessica without lots of makeup, letting her skin breathe and take a well-needed rest from all the foundation, shadow, and blush she normally wears in pics and in public. The shade of her golden hair looks amazing against her skin and her cheekbones show off her enviable bone structure. Jessica should take more of these natural selfies. We love ‘em and give this pic the thumbs up for “hot!”
13 Gaudy Getup – Not
Whatever Jessica was thinking when she stepped in public in this horrid jumpsuit couldn’t have been done while sober. Not only is this crazy getup super-gaudy and way too busy, but Jessica’s ample bosom is nearly busting its way through the top! The odd and boxy shape of the jumpsuit does absolutely nothing to flatter Jessica’s otherwise great body, and those platform shoes don’t help the situation either. Perhaps Jessica was interesting in testing out a new look or style, but this joke of a jumpsuit clearly missed the mark. Let’s all pray that the itty bitty strings holding the top of this outfit together were knotted sufficiently, or else everyone in town was sure to have an eyeful. Poor Jess… what a mess! This loud and lousy look gets a resounding “not!”
12 Denim Diva – Hot
Jessica looks like a fresh and feisty female in her cute light blue denim jacket and loose braided hair with playful bangs. That over-the-shoulder glance and subtle smirk make Jessica look alluring yet innocent at the same time. Her creamy makeup looks impeccable and her light blonde hair color brings out her deep brown eyes and works well with her luminous skin tone. A simple jean jacket is always a crisp and classic go-to look, and Jess’s version with pretty pink pastel flowers makes her look ultra-feminine and fun-loving. Whether she is dressed to the nines in an evening gown on a red carpet or in a comfy casual look such as this, Jessica can pull off nearly any end of the spectrum. Good genes and good jeans – this chick hits it out of the park, and we call this pic “hot!”
11 Bronzed Bombshell – Hot
Glowing tanned skin, shiny and bouncy hair, and carved-out collarbones for days make Jessica look like a sparkling statuette from the Golden Globes… only better. Her fresh shoulder-length “lob” and her barely-there hint of makeup make Jessica look natural, clean, and understatedly sexy. Her perfectly symmetrical face and shining brown eyes remind us of how beautiful the star is, and the camera seems to love her fantastic facial features. All Jessica needs to do is look deeply into the camera lens and she’s an instant perfect 10. Cameramen (and women) must love shooting when their spectacular subject is the always-gorgeous Jessica Simpson. If this pic doesn’t make you want to run out and get a spray tan, nothing will! This pic gets our vote for “hot” because it is sublimely sizzling!
10 Mature Mama – Not
This photo of Jessica could easily pass as President Donald Trump’s first wife, Ivana. Not that Ivana isn’t an attractive woman, but she is decades older than Jessica, and looking older than one’s actual age isn’t exactly a winning fashion statement. Jessica’s seriously severe makeup, ‘80s-style earrings, and side-swept bangs are not youthful or all too fashionable, for that matter. Her thick and heavy black turtleneck makes her look broad and her smile looks forced – probably because she isn’t too pleased with the work of her stylist and makeup artist. This look is far too mature for the youthful Jessica, and she certainly does not need all that gloppy makeup to look amazing. Less is more, and in this case, more is a mess. Jessica, sorry to say, but this look is a “not.”
9 Carpet Cutie - Hot
How sweet and sexy does Jessica look in this gorgeous photo? The sunlight shines right into the window illuminating the already bright and beautiful Jessica as she rolls around on a comfortable carpet. Her makeup looks fresh and glowing and her blonde hair is the perfect shade and length. The colors in the shoot are all natural and work well with Jess’s coloring, such as the olive green T-shirt and khaki undies she is sporting. That big bright smile is contagious and Jessica always knows how to work a room – even if she is the only one in it. This pic shows off Jessica’s spontaneous side and her great body as well. Who knew that a pic of a chick in a simple T-shirt and boy shorts could come out looking so fantastic? Clearly Jessica did! This pic is a “hot” one!
8 ‘70s Sweetheart – Not
Farrah Fawcett may have been able to nail this look back in the day, but Jessica’s attempt at recreating a classic style is falling flat. The styling of this shoot makes Jess look totally outdated and a tad sedated. Her hair color is quite gorgeous, but that ‘70s style was best left in the decade it came from. And we all know that Jessica is very well-endowed, but those big boobs are about to hit the floor! The shiny earrings and silky shirt are nice, and Jessica’s toned and tanned legs are to die for, but her awkward pose and dreary facial expression make us wonder if Jess is really feeling this look. Cuz we’re certainly not. That’s why we must give this pic a vote for “not” since it is not one we ever want to see again.
7 Proud Parent – Hot
Jessica posing with her mini-me is so cute that it is almost too much to bear. The two of these gorgeous gals are like two peas in a pod with their blond hair, big smiles, and fun attitudes. Jessica looks like she is so happy to be a mom to this cutie, and the joy and pride beams from her core and out every pore. She looks like a total natural at parenting and just being herself. Jess’s simple style and minimal makeup in this pic makes her fit for “mommy mode,” yet she still looks polished and ready to rock the business world. Her gold bangle bracelet and beautiful ring add the perfect amount of bling to her look, and those big hoop earrings frame Jessica’s face beautifully. Jessica is certainly one magnificent mama, and this pic gets a big shout out for “hot” through and through.
6 Fake Tan Fiasco – Not
Looks like someone used an old tube of self-tanner and turned into an oompa loompa right before our very eyes. Jessica, a natural tan is attractive, but this overly-orange complexion is not only unflattering, but will surely ruin that white shirt of yours. Sure, it is better to go for the fake tanner than to lie in the damaging UV rays of the sun or a coffin-like tanning bed, but if you are going to go for the sunless tanner, you better choose one that doesn’t turn you into Elmo. Not only is this tan a mess, but Jessica’s hairdo gets a thumbs down as well. Too much hair over one eye can have a gal bumping into walls and tripping over her own feet, even when they are bright orange and should be hard to miss. Jessica, this fake tan fiasco is a freak show. This photo gets a big and bold “not.” Orange may be the new black, but Jessica Simpson should never be the new orange.
5 Va Va Vest – Hot
Looking super-confident, happy, and fit, Jessica looks like a sweet and sassy country girl in her fitted brown vest and low-rise jeans. Always sporting a winning smile to show off her pearly whites, Jess is oozing sex appeal with her ample cleavage and bare washboard-flat midriff. Jessica’s toned and tanned arms look sleek and strong, and Jess looks like she is more than ready to take on the world. If you saw a woman looking this hot walking down your street, you’d never stop gazing out the window. She is a total knockout as she walks with her head held high, hands on her hips, and her sights set for adventure and success. A vest like this may not be for everyone, but then again, Jess fills it out so well that nobody else could possibly wear it better. This pic is a “hot” and you can tell Jessica knows it.
4 Golden Goddess – Hot
This breathtaking shot of the gorgeous Jessica shows off her perfect facial features and luminous dewy skin. Her blonde hair is shiny and light, her clear eyes are the most beautiful shade of brown, and her luscious lips are the envy of women everywhere trying fillers and serums to make theirs look half as sexy as Jessica’s do. As the fabulous celeb gazes magically into the camera, she finds the perfect pose to show off her natural good looks and subtle sexiness. Everything about her looks like it has been touched with a kiss of golden honey, from her skin tone to her lipstick shade. Simple shots of Jess like this one prove that she doesn’t need all the bells and whistles to prove she’s got the A-list look. Who agrees that this pic deserves the vote for “hot?”
3 Close Up Chaos – Not
You can’t win ‘em all, and this pic of Jessica is not one she’s going to add to the family photo album anytime soon. While the lighting and scenery of this photo are picturesque, Jessica was unfortunately snapped in a position that left her looking like she has the makings of a double chin. She also happens to look slightly constipated, but that’s just a wild guess. While Jessica’s smoky eye makeup looks nice, her hair could use a new coloring job. The bleached blonde look may work for some, but it makes Jess look washed out and out of style. Jessica is normally so ravishing that seeing a pic that isn’t great is a bummer, but at least we can now prove she’s human! Of course, this pic is getting a big honkin’ “not.” There’ll be better ones, don’t worry Jess.
2 Grinning and Winning – Hot
Jessica knows that her gigantic toothy smile is all she needs to show off in order to win us over. She has a gorgeous glowing grin that stretches from ear-to-ear, and if it doesn’t make you smile too, you must be seriously down in the dumps. Not only is Jessica’s smile a sight for sore eyes, but the rest of this photo is terrific too. Her hair is blown back off her face and looks light and bouncy, and her tanned skin and cream-colored top look great. Jessica looks youthful and carefree and has a great energy about her that comes right through the camera lens. She looks like a cute California girl with a sun-kissed aura and a casual spirit. Jess smiles bright for her photo shoots and we love seeing her so happy and positive. Giving this pic a vote for “hot” was a no-brainer.
1 Bundled Up Blunder – Not
Sometimes Jessica looks pretty in pink, but this bundled up version of the celeb is not as pretty as it is pink. Jessica looks a bit too fluffy and furry to come off as anything but Muppet-like, and her goofy expression doesn’t help her cause. Pink faux fur has never really been in style and those earmuffs aren’t exactly a fashion statement. Sure, it may be cold outside, but there are lots of better choices in outerwear, and Jessica can certainly afford them. Heck, she can even design them! While she doesn’t look altogether hideous, Jessica has seen better days, and we’ve seen far better pics of Jess. This coat needs to go to the back of Jess’s closet immediately and she can warm up by the fire instead. Jessica, you are getting a “not” for this chillingly bad ensemble.
