Reese Witherspoon: The Fugstory

With 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.

Leave a reply

Comments (42):

  1. Vanessa

    1. Legally Blonde came out TEN YEARS AGO?!?
    2. My favorite Reese is Reese walking down the street, in cute skinny jeans, flats, a nautical-looking striped navy shirt, and a coffee. You know all what I mean, right?

  2. Wren

    While there are certainly some ups and downs clothing wise… This slideshow reminded me of how freaking gorgeous her skin is! Sure she had a couple makeup mishaps and a few questionable hairdos, but for the most part she looks amazing from the neck up in these pictures regardless of whether the clothes are good.

  3. Julie

    I really REALLY enjoyed going through this slideshow. Especially to sigh wistfully over her hair, I forgot how great she looked as a brunette. I will always covet that yellow Globes dress, and the black and red polka dot from this year. The latter is so 40′s era movie star chic.

  4. pinkcheese

    Totally forgot about brunette, post-pregnancy Reese, but I loved it all. You’re right, that shade was just so lovely on her, and her clothes were great.

    And knee-cap canapes? Hilarious, even if all knee-joint related comments make me squirm. (Blew mine out in high-school, and I have to cover my eyes when they insist on replaying joint injuring tackles over and over and OVER again from every conceivable angle.)

  5. Susannah

    Her fashion choices were so very, very much better after she jettisoned Creepe Phillipe – she lost the frump and frou frou and started looking more polished and classic. Do you suppose she was dressing for him? Like, maybe in addition to looking generally grumpy and unwashed, he had some sort of bizarre Miss Kitty fetish?

  6. vandalfan

    She seems delightful, and boy am I glad I have some extra time at the office today to properly savor all 56. Here I go….!

  7. Lindy

    Awww, she’s soo cute! Ryan Phillipe always looked so bored or sullen with her. I hope she will be very happy with her new hubby.

    I love, love, love the purple ombre Nina Ricci dress.

  8. Elise

    I am a huge Reese W. fan. I agree she doesn’t always get it right, and OMG THOSE SLIDE 42 SHOES. Did she think she was going to have to use a college dorm shower or something? Yikes. But overall I tend to think of her as someone who looks generally good and doesn’t seem like a total nightmare to be around. Which has her better in my book than about 99% of Hollywood these days.

  9. corriner

    I really enjoyed this. Thank you Heather!

    Its unbelieveable how much BETTER she looks once her creepy obviously-has-a-thing-for-petite-blondes husband hit the road. She just looks so polished and fabulous, and started properly dressing her petite body type. I have no problem with her keeping it simple and straight forward, and maybe bordering on boring, I even think there are many-a-celebrity who should take a page out of her book instead of going all cracked out. It works more than it doesn’t.
    Brava Reese for being classy!

  10. Molly

    Wow. The 90′s were mean. And I wish she’d take a trip into Brunette land again!
    And #14- how is it that her face seems to be haunted by Courtney Love? The hair, no eyebrows, the vacant look in her eyes…
    Also, you reminded me how much I want to steal her post-divorce hair. Damn you.

  11. Stefanie

    I love her. Like seriously, love her.

    I also forgot how great she looks brunette.

    Another A+ Post.

  12. I.K.

    wow, she was STUNNING with that brown colour, i mean, look at this , she’s gorgeous with it. Although she’s certainly cute as a button with blonde hair too.

    I giggled out loud at slide 26 with the “killer eyes”, haha! Also at “HEM IT LIKE TAILORS ARE LEAVING OUR PLANET ON THE MORROW”. You girls are always so wonderful!

  13. Annie

    The only thing I disagree with is your hatred for the 2002 Oscar dress. I LOVED that dress. Granted, I’m a sucker for vintage gowns (and the illusion neckline is arguably weird) but I thought she looked like a 1920 screen siren. She had a look, and it worked for her.

    Definitely agree with Vanessa. She has a casual wardrobe I would kill, or at least maim, for.

  14. Leah

    Why is it that in the 90′s, it was OK to be attainably slim and soft, but today, celebrities have to be bone-solid perfection? Also, why the hate for Ryan? He can eat my toenails anyday.

  15. Al

    You know what problem 1996 didn’t have? Crotch or boob-revealing wardrobe malfunctions (or those ubiquitous teeny shorts with writing on the ass).

    As sad as it is to look back at what passed for fashion in the late 90s, when I went to high school, I would still take grungy frumps over some of the crazy, overly revealing fug that we see from starlets today. (And yes, I know I sound like my grandmother.)

    Thank you Reese for carrying the banner for our generation in that awesomely dowdy first photo.

  16. Kathy

    One thing is true about Reese… Her hair and make-up always looks great. No matter what she’s wearing, from the neck up, she always looks flawless. Can’t deny her natural beauty.

  17. Leigh

    I just love Reese. I think she’s adorable and seems somewhat down-to-earth.
    I don’t get her love affair with strappy slingbacks, though. I don’t need to see 95% of your foot.
    I also loved the brown hair and the blonde hair with bangs. I also agree that she was adorable pregnant. She needs a little extra weight to round out her face. When she gets too thin, she has that angular, Jennifer Aniston thing going on.

  18. Fuh Ugh

    I pretty much loved all of it with only the exceptions of the Kids Choice Awards (surfboard?), that horrible green top on the MTV beach and the Avon outfit with the godawful shower shoes. She is so fun to watch! And, although you don’t love her taste in shoes, I do. Demure, feminine and pretty – 56 slides and not one single pair of platform hooves on her feet EVER. For that alone, she has my undying fashion love.

  19. Chicklet

    The thing that stands out for me is that even Reese’s mistakes are *tasteful*. Sure, some of it was frumpy, but at least she’s not looking back at her first decade in the business and thinking, “Man, I wish I hadn’t revealed my lady-business at that gig.” (Taylor Momsen, I’m looking at shielding my eyes from you.)

  20. Sally

    I started to wonder if Creepe Philippe really did have a thing for gnawing on knee caps or if Reese’s were just hideously deformed. Thank God she found her legs after the divorce and they’re CUTE! And ya know, who among us could withstand a 15 year fashion retrospective? Certainly not me; in fact, don’t even look at what I have on today.

  21. exquisite red

    I loved this slide show too. And I never realized how creepy Ryan was! Hooray Reese, for keeping things interesting while also keeping everything…in. =)

  22. Gigi

    I feel for Reese: it is hard to both be from the South and to resist matching your shoes to your outfit.

    I agree with Vanessa: Casual Coffee Fetching Reese is best!

  23. Jennifer

    Loved this! There is a definite difference in style With Ryan and After Ryan. For the better!

  24. Another Leah

    The purple ombré dress is actually my favorite dress of all time.

  25. yeahandalso

    my all time fav Reese look is the hot pink dress from the Legally Blond premier…especially because Ryan had a mohawk and a hot pink tie to match her dress

  26. vandalfan

    She just looks so cheerful and happy to be photographed, and humble, kind of like Sally Field and her Oscar acceptance speech, “You like me! You really like me!” I wish Kristin Stewart and others would take some attitude lessons from Reese.

    And the shower shoes are exactly what they give the jail inmates to wear with orange jumpsuits to their arraignments around these parts.

  27. Sneza

    You’re right — her footwear has been too bare throughout the years, especially the early years.

    Also — in that dress that causes the look wonky tan lines, I think she already had wonky tan lines, and the the dress just further wonked out the tan lines.

  28. jean

    Wow, that was epic! She’s been around for quite some time. I loved the brown hair on her too. It’s a shame that “blonde” seems to be her brand. She makes looking good seem effortless too. I never wonder about her workout regieme or if she washes her hair in bottled water or whatever. Of course there’s work involved. She’s the mother of two, but she doesn’t freak me out like January Jones or Jennifer Anniston.

  29. cb

    There was an all white number she did one day in DC (there for the corespondent’s dinner?) and she looked amazing.

  30. Lina

    I am so FOND of her. And I envy her closet quite a bit, too.

  31. G

    What I like most is her expressive face. Too many stars look grim or bored in photos and she looks like she’s reacting in a warm and human way. I bet she’d be fun to have a beer with.

  32. Danni

    I think everything became better after she realised that on-the-knee if much more flattering on her than mid-calf (which is rarely flattering on anybody).

  33. Im

    I love reese, but I feel like there were more mistakes then victories in this slideshow…

  34. Su-Yin Johns

    i enjoyed every slide, and i really hope you plan to do this for other celebs! reese is a classy lady and that’s really coming out now. her make up improved 100% after avon called, and her clothes improved about 1000% after jettisoning the baby daddy. amazing what hemming a skirt to the correct length can do for you – lesson learned.

  35. Nicole

    In slide 17, does that look like Heather Morris holding a chihuahua?

  36. Popcouver

    I will never get the toenails as pizza toppings comment out of my head. Another hilarious post! You had me laughing out loud, Heather.

  37. Miranda

    I’m unhappy to say I feel like this slideshow had the opposite of the intended effect: I still feel pleasantly indifferent about her clothing choices (she looks good but it’s not quite my style or what interests me in fashion), but now I know her taste in shoes makes me want to go back to bed. Even if I’m reading GFY in bed, as I often am. Now every time I see a picture of her I’m going to be frantically checking the shoes for improvement, or trying not to look so as not to have my pleasant indifference ruined by a stab of shoe misery.

  38. Mukel

    I think she looks great. But ah, 1996! That looks like me in my Yearbook Editor photo, 12th grade. Alas, now that I have more money and the fashion is better, I need to lose 30 pounds! The cruelties of life.

  39. A.J.

    I didn’t realize until this slideshow that my ex-husband and Ryan Phillipe both have that same non-smile, scary eye stare in pictures. Like it would have killed either one of them to smile! Maybe that should have been a sign to both me and Reece…

  40. Aria

    The thing about Reese (or at least from these photos), even when it’s bad, it’s not that bad.

  41. Daryl

    I still have that black beaded DKNY sweater ..

  42. Hima

    Slide 21 is my favorite — where Reese is a brunette and “thematically” going as June Carter Cash. She looks so wistful and romantic, with the hair, and dress and shoes and background. Gorgeous.