The Fug Girls: Jessica Simpson’s Love Life and Fashion Choices Are Intertwined
1 of 17
Back to the Intro

The Fug Girls: Jessica Simpson’s Love Life and Fashion Choices Are Intertwined

1 of 17

January 2000: Dating Nick Lachey

Photo: Steve Granitz/WireImage/Getty Images
This forgotten abomination illustrates how comparatively unfamous Jessica was back in 2000 — a more innocent time when she was just Nick Lachey's singing girlfriend. Who just happens to be wearing a bitter cocktail of Sharon Stone, Tawny Kitaen, and a Victoria's Secret clearance sale.
2 of 17

December 2000 and April 2001: Dating Nick Lachey

Photo: Barry King/WireImage/Getty Images; Steve Granitz/WireImage/Getty Images
Yes, you are looking at feathered arm warmers and a sleeveless metallic denim duster worn over matching shorts — proof that Jessica's repeated abuse of jeans has deep roots. It's hard to believe that anyone who dressed like this ever got a date, but girlfriend is showing a lot of skin, and this was the dark ages — an era during which Hilary Duff and Lindsay Lohan nearly came to blows over Chad Michael Murray, and 98 Degrees was a real band.
3 of 17

October 2002: Engaged to Nick Lachey

Photo: Amy Graves/WireImage/Getty Images
One week before she married Nick, Jessica's wardrobe confirms what the previous looks only suggested: Happiness is detrimental to her eyesight. It also apparently makes her skin sticky as double-sided tape; how else to explain making it through the night without that bodice making merry with her ankles? Her cups don't runneth over so much as want to runneth away.
4 of 17

November and August 2003: Married to Nick Lachey

Photo: Frank Micelotta/Getty Images; Dimitrios Kambouris/WireImage/Getty Images
By 2003, thanks to the success of Newlyweds, Jessica's star was on the rise, but her marriage was under the microscope — and looking more awkward by the day. She reacted by trading the vaguely hoochie, headline-baiting gear of the low-level pop star for slinky glamour. We applaud her for reaching for class, but unfortunately, she was unaware of where to look for it.
5 of 17

August 2004 and February 2005: Married to Nick Lachey

Photo: Frank Micelotta/Getty Images
The rumored disrepair of the Lachey-Simpson union was starting to show — check out the awkward body language here — but Jessica's career was never more solid, and that confidence is reflected in a spate of pretty and polished clothes. Which we suspect means Jessica was paying for the services of a professional stylist, just on the off chance she became available and needed a new love match made in PR heaven.
6 of 17

December 2005: Post–Nick Lachey

Photo: Mark Mainz/Getty Images
Jessica and Nick filed for divorce at the end of 2005, at which point she demonstrated that she missed the lesson everyone else in the world learned — the way to handle a breakup (much less a public one) is to show up at all subsequent events looking incredibly hot. The only conclusion here is that the failure of her marriage left her depressed and unable to judge whether or not she was putting on a muumuu.
7 of 17

June and January 2006: Pre–John Mayer

Photo: Kevin Mazur/WireImage/Gett Images; Peter Kramer/Getty Images
By mid-2006, sexy single gal Jessica made a great return to fashion form. These dresses are working with her, not against her — which is more than can be said for her taste in men, as Jess allegedly dallied with the likes of Dane Cook, Johnny Knoxville, and Maroon 5's Adam Levine. In retrospect, how did we not see John Mayer coming?
8 of 17

October 2006: Dating John Mayer

Photo: Frazer Harrison/Getty Images
By now, Jessica and John Mayer were two months into an on-off fling. The instability and drama of dating somebody who doesn't seem to be terribly into you probably accounts for how depressed she looks — and possibly also for the fact that she is about two eyes of newt away from whipping out a cauldron and hexing every Y chromosome in Los Angeles County.
9 of 17

April 2007: Dating John Mayer

Photo: Splash News
This look smacks of trying to hang onto the jerk you're dating by changing anything he mocks about you — say, your blondeness, your ownership of a waist, or your hitherto insane habit of not wearing pleated pelvic pockets that resemble lonely, deflated balloons.
10 of 17

May 2007: Dating John Mayer

Photo: Evan Agostini/Getty Images
Jessica took Mayer with her to the Met Ball. She also brought her best showgirl look, which might have worked on a lady of lesser chest, but made her look a bit desperate. Was there anyone in America who didn't know that this particular relationship wasn't going to end well? Why didn't André Leon Talley drag this poor girl into the bathroom and give her a heads-up — or at least loan her his caftan?
11 of 17

September 2007: Post–John Mayer

Photo: Bryan Bedder/Getty Images
By this time, Mayer and Simpson were kaput — and, surprise surprise, she was back to blonde. We'd say that Jessica looked more like herself, except that this self is unusually polished. If this is how good she can look single, she should remain that way forever.
12 of 17

September and August 2008: Dating Tony Romo

Photo: Splash News
Instead, merely two months later, Jessica was dating Dallas Cowboys quarterback Tony Romo, which somehow led to her reinventing herself as a country-music singer. Surely the entire Academy of Country Music was offended by her interpretation of "Western" attire, which appears derived from a Hee Haw marathon and a community theater production of Lil' Abner.
13 of 17

January and March 2009: Dating Tony Romo

Photo: Splash News
The more Jessica trumpeted her bliss with Tony, the more carelessly insane her wardrobe got, until she landed at a chili cook-off in January 2009 with her groin swaddled in discount-denim Mom Jeans. We know everything is bigger in Texas, but that's not an acceptable excuse for high-rise pants so wretched they could scare the beans out of the beef — or for giant formal platform pumps with cutoffs that look like Britney's cast-offs.
14 of 17

November 2009 and April 2010: Post–Tony Romo

Photo: Splash News
Simpson and Romo split in July — allegedly the night before her 29th birthday. Unlike the last time she was single, though, Jessica had both gushing words of love coming back to bite her and major professional problems, which we suspect jointly account for how hard she was trying with her wardrobe. Nothing says "Next!" like something super tight, shiny, and short.
15 of 17

October 2009: Post–Tony Romo

Photo: Jason Merritt /Getty Images
This look can't even be blamed on a dude: Sony Nashville had dropped Jessica, and her awkwardly titled film Major Movie Star got pushed straight to DVD. Add to that her ongoing romantic struggles (and the tabloids' obsession with calling her a dried-up spinster), and it seems that the stressed-out Simpson got lost on the way to Sophisticated Celebrity and instead accidentally veered into High Schooler Attempts Business Casual at Junior Achievement Awards Banquet in Local Applebee's Party Room.
16 of 17

July and September 2010: Dating Eric Johnson

Photo: Splash News
Jessica's current fiancé enters the picture, ushering in a period of almost unprecedented wardrobe awkwardness, ranging from wholly inappropriate sheer caftans to unflattering fringed cocktail dresses. These are not the insane eyesores of her unfamous youth, when she lacked the resources to know better; these are things she has chosen. Is she love-drunk? Or giving up?
17 of 17

September 2010: Dating Eric Johnson

Photo: Bryan Bedder/Getty Images
In her last major public appearance before her engagement, Jessica judged the Project Runway finale looking like the retired showgirl mother of an Oompa-Loompa. Please, somebody, kidnap her and deliver her to Rachel Zoe's doorstep — or lock her in a convent without her credit cards until she takes a vow of celibacy. Anything to remind this girl that her greatest accessory is not a man but a mirror.


Latest News from The Cut

Kavanaugh Accuser Christine Blasey Ford is Moving Out of Her Home Due to Death Threats

She also hired private security.

Julia Louis-Dreyfus in One of the 200 Women to Sign Letter in Support of Christine Blasey Ford

Ford and Louis-Dreyfus attended the same high school.

Senator Mazie Hirono Wants Men to ‘Just Shut Up’

She also wants them to do the right thing.

Trump’s Dick Reportedly Looks Like Toad From Mario Kart

Stormy Daniels tells all about the president’s “Mario Kart” genitals and “Yeti pubes” in her new book.

A Running List of Excuses Team Kavanaugh Has Tried Out

Their tactics in dealing with the misconduct allegations have been numerous, and sometimes contradictory.

How to Get Mandy Moore’s Surfer-Inspired Smooth Emmys Hair

Soft, beachy waves.

A Socially Conscious Way to Buy a New Watch

PAID STORY: Meet Citizen, a socially conscious watchmaker.

Report: Toad Is Distraught About Being Shaped Like Trump’s Dick

A very sad day for our happy little friend.

Here’s Emma Stone Riding a Merry-Go-Round

For a new Louis Vuitton film.

These Floral Dresses Feel Very of-the-Moment (and They’re on Sale!)

From the British label Preen by Thornton Bregazzi.