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# Reese Witherspoon: The Fugstory
- URL: https://go-fug-yourself.ghost.io/reese-witherspoon-the-fugstory/
- Published: 2011-04-22T17:00:58.000Z
- Updated: 2011-06-02T06:06:32.000Z
- Author: Heather
- Tags: #wp, #wp-gallery, #slideshow, #Import 2026-10-07 07:27

## Reese, 1996

![](https://storage.ghost.io/c/bf/b9/bfb99790-924d-4e41-a7e6-5e3c6e04fe57/content/images/static-gofugyourself-com/uploads/2011/04/reesewitherspoon1_52059799.jpg)

Here, Reese was promoting "Fear," the movie where she and Mark Wahlberg hook up and then he goes insane, or something. I don't know. Alyssa Milano is in it. That tells you things. (Nothing against Alyssa; her taste in movies just is not really very good.) I can't imagine any of us thought Reese, at this point, was going to win an Oscar and be major A-list, but she was cute. The dowdy clothes, not as much, but then again, in 1996 this was probably the height of chic. 1996 had problems.

## Reese, 1999

![](https://static.gofugyourself.com/uploads/2011/04/reesewitherspoon_2_851926.jpg)

This is from the "Cruel Intentions" premiere, and this outfit is aptly enough having cruel intentions all up over her. THIS is the one where Reese wakes up in a cold sweat screaming, "RENAISSANCE FAIRE!!!!" and Jim Toth is like, "Ren Faires are so hot right now, let's get that one going," and Reese smacks him in the head with a leg of mutton.

## Reese, 2000

![](https://static.gofugyourself.com/uploads/2011/04/reesewitherspoon_3_2220932.jpg)

As simple and boring as it gets, but then again, what else could she do? She didn't dare compete with Ryan Phillippe's hair. You can't fight with that mop. You can only hope to contain it, and then use it to clean behind the loo later.

## Reese, 2000

![](https://static.gofugyourself.com/uploads/2011/04/reesewitherspoon_4_1141082.jpg)

Man, this girl really loved shapeless sheaths.

## Reese, 2000

![](https://static.gofugyourself.com/uploads/2011/04/reesewitherspoon_5_2246957.jpg)

Yes, that IS a velvet blazer.

## Reese, 2001

![](https://static.gofugyourself.com/uploads/2011/04/reesewitherspoon_6_1316357.jpg)

Reese appears sort of surprised by how decorated she is. Or maybe she's just surprised she's at the Golden Globes when her 2000 film credits included "Little Nicky." Can we just stop and discuss how surreal it is that the Reese Witherspoon we know today was in "Little Nicky"?

## Reese, 2001

![](https://static.gofugyourself.com/uploads/2011/04/reesewitherspoon_7_1326256.jpg)

There's a lot happening here. First, Ryan Phillippe has a Mohawk. Second, his tie sort of matches Reese's dress. Third, he's staring down it as if he's never seen its contents before. And fourth, that heinous dress doesn't fit. I'm guessing the all-pink motif is an attempt to clothe herself thematically, but in fact, Elle Woods would be horrified, proclaim Reese illegally blonde, and tell her to have that creepy serial killer on her arm arrested.

## Reese, 2001

![](https://static.gofugyourself.com/uploads/2011/04/reesewitherspoon_9_1327340.jpg)

Girlfriend loves a blazer. Which is fine. But I'm realizing through this slideshow that oftentimes I REALLY have issues with her taste in shoes. Also, is she wearing a tube top under that jacket? Or just a tank top that rode up?

## Reese, 2001

![](https://static.gofugyourself.com/uploads/2011/04/reesewitherspoon_10_675383.jpg)

I'm guessing the demure, almost Queen Elizabeth-like restraint in this outfit is because they were at the premiere of Gosford Park, and Reese was trying to be oh-so-proper. Also, maybe she's trying to compensate for the fact that even when he's in a fancy suit, Ryan Phillippe has a scummy sticky-sheen to him that makes me wonder if he peeled himself off the floor of a bar recently -- kind of like how I used to feel about Carson Daly, back when he was engaged to Tara Reid. And let's pause and laugh about THAT.

## Reese, 2002

![](https://static.gofugyourself.com/uploads/2011/04/reesewitherspoon_11_692733.jpg)

Yes, Reese, you are hearing me right: NO. This looks like Victoria told her Secret to someone at Contempo Casuals.

## Reese, 2002

![](https://static.gofugyourself.com/uploads/2011/04/reesewitherspoon_12_706405.jpg)

Apparently I really need to sit down with Reese and tell her it's OKAY to wear shoes that don't show 90 percent of your foot. Really. REALLY.

I wish I liked the dress, but it's just all a bit Brothel Lampshade for me. And I think Ryan Phillippe wants to eat my teeth.

## Reese, 2002

![](https://static.gofugyourself.com/uploads/2011/04/reesewitherspoon_13_2259998.jpg)

Slacks and a Flowbee: How Reese Witherspoon Spent Her Summer Vacation.

## Reese, 2002

![](https://static.gofugyourself.com/uploads/2011/04/reesewitherspoon_14_1428531.jpg)

Hey, Reese, those shoes are a MASSIVE IMPROVEMENT THANK YOU JEBUS. The dress is... okay? But the ribbon feels like an afterthought rather than an adorable detail. Unfortunately, all of this is overshadowed by how Ryan Phillippe wants to floss his teeth with my aorta.

## Reese, 2003

![](https://static.gofugyourself.com/uploads/2011/04/reesewitherspoon_15_2122157.jpg)

Preggo! And cute. Also, how nice of Ryan to cover up his eyes so that we can't TELL he's planning how to use our toenails as a pizza topping. It seems that no matter what Reese had on her body, Ryan was often an outfit-ruining accessory.

## Reese, 2003

![](https://static.gofugyourself.com/uploads/2011/04/reesewitherspoon_16_2127217.jpg)

Dear MTV: This wasn't a nice thing to do to a pregnant lady.

## Reese, 2003

![](https://static.gofugyourself.com/uploads/2011/04/reesewitherspoon_17_2127832.jpg)

Now THIS is more like it. Get the pregnancy boobs out and WORK 'EM, Reese! I am noticing that girlfriend really likes the lacy look, though.

## Reese, 2003

![](https://static.gofugyourself.com/uploads/2011/04/reesewitherspoon_18_2176822.jpg)

These last few photos pimping the Legally Blonde sequel... I mean, did anyone else completely forget that movie happened? Obviously, those red shoes were pregnancy-comfy, which I appreciate, and this is a cute festive summer dress. Personally, I love Pregnant Reese. It rounds her out nicely. When she's too skinny her chin gets sharp enough to slice cheese.

## Reese, 2003

![](https://static.gofugyourself.com/uploads/2011/04/reesewitherspoon_19_2189407.jpg)

Red shoes again! And a cute dress. And kicky hair. And a husband who is maybe marginally less sullen. MARGINALLY.

## Reese, 2004

![](https://static.gofugyourself.com/uploads/2011/04/reesewitherspoon_20_51179551.jpg)

Post-baby, Reese went brown while shooting "Walk The Line," and I actually loved it on her. The color flattered her skin tone and her eyes so nicely. And this dress is cute. Well done, Post-Baby Reese.

## Reese, 2004

![](https://static.gofugyourself.com/uploads/2011/04/reesewitherspoon_21_51251649.jpg)

See? So cute! Reese is seriously very often my Casual Dress Hero.

## Reese, 2004

![](https://static.gofugyourself.com/uploads/2011/04/reesewitherspoon_22_51263629.jpg)

Reese really likes to go thematic -- pink for the first Legally Blonde, and this is totally June Carter Cash to me.

## Reese, 2004

![](https://static.gofugyourself.com/uploads/2011/04/reesewitherspoon_23_51264794.jpg)

You can try to suppress it, Ryan, but you can't hide your true nature. I am not distracted by how cute Reese looks in aqua. NO SIR. YOU ARE PLOTTING TO EAT MY KNEECAPS AS A CRUDITE.

## Reese, 2005

![](https://static.gofugyourself.com/uploads/2011/04/reesewitherspoon_24_52700424.jpg)

Not my favorite of her haircuts, nor her dresses. Suddenly I'm realizing Reese didn't ALWAYS pluck my heartstrings when it came to fashion. This is just sort of blah -- very her, in that the hemline is a bit long and it's very simple, but otherwise not that much to recommend it. At least Ryan's hair looks less like an olive-oil shower rained down on the Play-Doh Mop Top Hair Shop.

## Reese, 2005

![](https://static.gofugyourself.com/uploads/2011/04/reesewitherspoon_25_53136084.jpg)

Girl. Those PANTS are wicked, and not in the Canadian way where it's a compliment. I'd make a mother-of-the-bride joke, but mothers of the bride the world over would show up at my house and egg it.

## Reese, 2005

![](https://static.gofugyourself.com/uploads/2011/04/reesewitherspoon_26_55321718.jpg)

This reminds me a bit of what she just wore to the Water For Elephants premiere -- a slightly less polished version, a bit floatier, a bit off, not awesome but probably not awful either. The tulle "straps" keep making me think she has a wonky tan line.

## Reese, 2005

![](https://static.gofugyourself.com/uploads/2011/04/reesewitherspoon_27_55396390.jpg)

Another slightly ill-fitting, slightly too long dress. I love how terrified she looks by Joaquin Phoenix. Girlfriend is starting to smell the crazy. Meanwhile he is doing his best to woo her by out-Phillippe-ing Phillippe: "You love your killer-eyed husband so much? I WILL SHOW YOU KILLER EYES."

## Reese, 2005

![`](https://static.gofugyourself.com/uploads/2011/04/reesewitherspoon_28_55732915.jpg)

HEM IT, REESE. HEM. IT. HEM IT LIKE TAILORS ARE LEAVING OUR PLANET ON THE MORROW.

## Reese, 2005

![](https://static.gofugyourself.com/uploads/2011/04/reesewitherspoon_29_55976063.jpg)

Well... I like the shoes. I can't tell if I mind the dress. It's sort of cute, and sort of like being trapped in a florist's fridge.

## Reese, 2005

![](https://static.gofugyourself.com/uploads/2011/04/reesewitherspoon_30_56011076.jpg)

A night without Ryan is like... a night without Ryan. \[Did this slideshow turn into Fug The Marriage?\]

## Reese, 2005

![](https://static.gofugyourself.com/uploads/2011/04/reesewitherspoon_31_56080893.jpg)

Oh, girl. GIRL. I don't even remember this one happening. I clearly blocked it out. Ryan, however, has a look on his face that says, "Yeah, I blocked that out... IN THE LIMO. IF YOU KNOW WHAT I MEAN."

## Reese, 2005

![](https://static.gofugyourself.com/uploads/2011/04/reesewitherspoon_32_56152833.jpg)

Intriguing. I don't remember this, either. Where was I? I know this Web site existed. Were we napping? How could we have missed this? It's the matador's cloak and we are the bulls. We would be racing toward it. ... Actually, I don't hate it.

## Reese, 2006

![](https://static.gofugyourself.com/uploads/2011/04/reesewitherspoon_35_golden-globes-fug-carpet-reese-01-2006.jpg)

So, if I remember correctly, there was a snafu about how Reese's vintage Golden Globes dress had been worn before by Kirsten Dunst. The real question is why anyone was allowed to wear it, when it had obviously been ravaged by hungry wolves who were trained to eat only chain mail.

## Reese, 2006

![](https://static.gofugyourself.com/uploads/2011/04/reesewitherspoon_36_sag-awards-fug-carpet-reese-wi-01-2006.jpg)

Hmm. This was awkward and slouchy and wrinkled. Reese was a nominee -- you'd think she'd have gone the extra mile, rather than turned left and driven three miles in the wrong direction before realizing she was lost and then getting a flat tire when she tried to make an illegal U-turn.

## Reese, 2006

![](https://static.gofugyourself.com/uploads/2011/04/reesewitherspoon_37_57003949.jpg)

At the time of these Oscars, I remember thinking that somewhere, Ava Phillippe was combing the hair of a Barbie wearing a miniature replica of this exact gown. And that Ryan really could have taken two seconds to shave. And that he seemed hammered and sort of mocking when he whooped it up during her acceptance speech. And that they were totally going to get a divorce. I suspect I was right on ALL counts.

## Reese, 2006

![](https://static.gofugyourself.com/uploads/2011/04/reesewitherspoon_34_56352227.jpg)

I love that she's recycling, like, the one pair of shoes she's ever worn that DON'T make me concerned for how far her toes are jutting out of them. But although her hair looks fantastic, I'm not sure I see the wisdom in wearing a dress that looks like it was balled up in her purse not five minutes ago.

## Reese, 2007

![](https://static.gofugyourself.com/uploads/2011/04/reesewitherspoon_39_73004899.jpg)

When Reese stepped out in this one, it was post-divorce, and this one kind of screamed "HELLO WORLD I HAVE NEW BANGS AND YOU CAN'T STOP LOOKING AT ME AND I WIN I WIN I WIN." And she was right. I kind of loved this. If anyone could pull off cocktail length at the Globes, it would be Reese.

## Reese, 2007

![](https://static.gofugyourself.com/uploads/2011/04/reesewitherspoon_40_well-played-reese-witherspoon-01-2007.jpg)

Another one I like, yet after the bold red shoes with the canary dress, Reese is back to matching her shoes to her clothes. Not loving that part of it. But if I could fit my rear end into this dress I would borrow it. If we were friends. Which we won't ever be, after I made all those comments about her ex making me afraid for my life.

## Reese, 2007

![](https://static.gofugyourself.com/uploads/2011/04/reesewitherspoon_41_73421044.jpg)

I liked this one as well -- the ombre works without being glaring. I tend to think Reese's style stepped up in quality once she was single, as if she either got a new stylist or the person she was working with realized Reese was a hotter tabloid commodity without the ball and chain, and sucked up to designers accordingly.

## Reese, 2007

![](https://static.gofugyourself.com/uploads/2011/04/reesewitherspoon_43_77433408.jpg)

I don't think I knew I needed a tweed day dress until right this second.

## Reese, 2007

![](https://static.gofugyourself.com/uploads/2011/04/reesewitherspoon_44_77435004.jpg)

This red dress looked simple and potentially very cute, except something bothered me about the right strap. It didn't look very obedient.

## Reese, 2007

![](https://static.gofugyourself.com/uploads/2011/04/reesewitherspoon_4477434910.jpg)

AHA. GOTCHA.

## Reese, 2008

![](https://static.gofugyourself.com/uploads/2011/04/reesewitherspoon_45_81523006.jpg)

You'd think that I'd object the most to the fact that this outfit artificially doubles Reese's width. But no. It's the SHOES. THE SHOES MUST BE DESTROYED. I wonder if they're slippers, and she'd just gotten an Avon pedicure, or something, but still. They should not have been allowed to happen. They give kittens ulcers.

## Reese, 2008

![](https://static.gofugyourself.com/uploads/2011/04/reesewitherspoon_46_cma_awards_fug-or-fab_carpet_r_1-11-2008.jpg)

Well, this was an experiment. So was Crystal Pepsi.

## Reese, 2008

![](https://static.gofugyourself.com/uploads/2011/04/reesewitherspoon_47_83770967.jpg)

Oooh, Reese, splashing out with the funky footwear. I like this outfit a lot more than I liked this movie. Of course, I didn't see this movie. But I am okay with the snap judgment.

## Reese, 2009

![](https://static.gofugyourself.com/uploads/2011/04/reesewitherspoon_48_70871_84987121-419x583.jpg)

Another experiment. People fault Reese sometimes for being simple verging on boring, but sometimes I think any efforts to combat that -- like with this fancy take on being TP'd -- swallow her whole. She doesn't have a great eye for what dominates her. Insert joke here about inappropriate things.

## Reese, 2009

![](https://static.gofugyourself.com/uploads/2011/04/reesewitherspoon_49_85315447.jpg)

Aw. Y'all know how stabby satin can make me, but she's so cute that I can't get mad at this.

## Reese, 2009

![](https://static.gofugyourself.com/uploads/2011/04/reesewitherspoon_50_85380026.jpg)

It's hard to stand next to a giant one-eyed blob and still be the center of attention, but Reese is pulling it off. She'd better add that to her resume under "special skills."

## Reese, 2009

![](https://static.gofugyourself.com/uploads/2011/04/fug_or_fab_reese_witherspoon-03-2009.jpg)

I loved this, but a lot of people thought it looked like Christmas-themed aluminum foil. But to me she looked sort of fierce and in-your-face, which is not something I usually think about Reese Witherspoon unless I am watching Sweet Home Alabama and thinking about how fiercely in-my-face annoying it is.

## Reese, 2009

![](https://static.gofugyourself.com/uploads/2011/04/reesewitherspoon_55_106135573.jpg)

Had I written about this, I'd have Fug or Fabbed it, I think. So much of it works, except for how she should never have sat down anywhere after putting it on -- like, have someone roll you over Hannibal Lecter-style, if you have to, girl.

## Reese, 2009

![](https://static.gofugyourself.com/uploads/2011/04/reesewitherspoon_52_92400897.jpg)

Sigh. Why can't my hair do that? I mean, aside from how we have totally different hair?

## Reese, 2010

![](https://static.gofugyourself.com/uploads/2011/04/reesewitherspoon_53_96224817.jpg)

This speaks to Reese's established love of lace, but I like it much better than some of her others -- it's pretty, it's feminine, and it fits well. Also, I am out of things to say about Reese Witherspoon. How about those Gyllenspoon years, huh? Was that a waste of tabloid ink or what?!?

## Reese, 2010

![](https://static.gofugyourself.com/uploads/2011/04/reesewitherspoon_56_107235079.jpg)

I want this.

## Reese, 2010

![](https://static.gofugyourself.com/uploads/2011/04/reesewitherspoon_57_well-played-reese-witherspoon-2-12-2010.jpg)

I want this also.

## Reese, 2011

![](https://static.gofugyourself.com/uploads/2011/04/reesewitherspoon_-58_Reese-Witherspoon.jpg)

I don't want this, really. But I liked it on Reese. Compare this to the giant black lacy thing, or the blue Rodarte, and I think you can see why she kept it safe here -- she needed not to be overshadowed by her clothes, because all the press about her had been all REESE'S WEDDING JOY and BABY JOY FOR REESE? and REESE'S JOY JOY, and why ruin a good joy run?

## Reese, 2011

![](https://static.gofugyourself.com/uploads/2011/04/reesewitherspoon_59.jpg)

I DEFINITELY don't want this. Yikes, girl. A thousand pregnancy rumors were born of this outfit, and so far none of them are true.

## Reese, 2011

![](https://static.gofugyourself.com/uploads/2011/04/reesewitherspoon_60.jpg)

And here we are. I really liked this on her, but I kind of wish she were still funking up her footwear, instead of her usual bare-bones slingback. But think of the first pictures in this slideshow, and now look at this one again. It's not easy to grow up in front of the cameras, but Reese has done it, bit by bit, and come out the other end in an enviably chic place. Can the likes of LiLo say the same? I think not.

[Reese Witherspoon: The FugstoryWith Water For Elephants coming out, and the fact that I watch Cruel Intentions pretty much any time I find it airing on cable, I decided it might be fun to do a look back at Reese Witherspoon's fashion through the ages. Whenever anyone asks me who I think is one of Hollywood's best-dressed celebs, I name-check Reese, because I've always found she has an endless supply of really cute cocktail and day dresses that are a lot more relateable to me than red-carpet gowns. This slideshow MIGHT have me re-thinking that... but, not entirely, because she nails it more consistently than she doesn't. However, there are certainly some doesn't's in here, beginning with a lot of what she wore when she was coming to fame, and then some stuff in the middle I had completely forgotten existed. Do you think Reese has forgotten any of them? Or do you think she woke up recently and rolled over and poked Jim Toth in the back and said, "Dude, this one time? I looked like a refugee from the Singles auditions. WHAT WAS WRONG WITH ME?" At which point he was probably all, "I could get Singles II greenlit for you," and across town someone at Us Weekly sat up straight as an arrow in bed and began casting it with Jennifer Aniston, Jessica Simpson, Jessica Biel, Renee Zellweger, and, like, Ashley Greene.![](https://storage.ghost.io/c/bf/b9/bfb99790-924d-4e41-a7e6-5e3c6e04fe57/content/images/static-gofugyourself-com/uploads/2011/04/reesewitherspoon1_52059799.jpg)](https://go-fug-yourself.ghost.io/reese-witherspoon-the-fugstory-04-2011/)