Look We Love: Rolled Cuffs - Celebrity Style and Fashion from WhoWhatWear

Typically, we’re not prone to conspiracy theories, but the recent blitz of boyfriend jeans made us stop and ponder a couple of things. First of all, why did such a vast range of celebrities start wearing this specific style all at the same time? Secondly, why did the seemingly perfect denim storm happen now, during the hottest time of year, when most people are reaching for their shorts? We’re not sure who the mastermind is behind all these rolled cuffs (spotlight hungry ankles, perhaps?), but one thing we do know is that this is a look we love.

Clearly the celebs are smitten too, as you can tell from the random range of women we’ve spotted wearing their cuffs turned up. Katie Holmes is particularly devoted to this look; she’s worn a favorite pair of Prps Barracuda Jeans ($385, available at Barneys this week) repeatedly this month. Seen here en route to rehearsals for the highly anticipated Broadway play All My Sons, Holmes wore her turned-up hems with The Row’s S/S 08 Burnout T-Shirt ($260, at Bergdorf Goodman in New York), a Couture Couture cardi, and a pewter pair of Lanvin Metallic Ballet Flats ($550). The equally practical Reese Witherspoon also chose to wear flats with her cuffed jeans. Witherspoon wore our favorite pair—Current/Elliott’s The Boyfriend Cropped Jean ($226)—in the Super Loved Destroy wash while shopping in Los Angeles last week.

The rolled-cuff jean also allows you to show off an interesting pair of shoes or booties, as Sarah Jessica Parker, Amanda Peet, and Rachel Bilson demonstrate. SJP wore a slim charcoal pair of Balenciaga Jeans ($300, 212.206.0872) with some stern black booties while in Berlin as a part of the SATC: The Movie promotional tour. Amanda Peet also chose to accessorize her partially pegged pair of faded jeans with strong black shoes. The new mom wore a Huck Finn-styled pair of Earnest Sewn Decca 233/Dudley ($186) jeans to the premiere of Pineapple Express. Our final look comes from reader favorite Rachel Bilson, who was snapped shopping in a turned-up pair of skinny jeans. Her Paige Denim Roxbury Crop Skinny Jean ($179) nicely showed off a standout pair of nude Maison Martin Margiela Open Toe Ankle Boots ($595), which we found online in pale mint green. We also suggest taking a look at the new Triumphh Heel ($109.95) from Steve Madden, as it greatly resembles the MMM version, but, of course, costs much less. But back to the jeans...

Whether you like them relaxed and baggy or trim and tapered, we have a rich selection of choices right now. In addition to the aforementioned options, we also like a classic pair of Levi’s 501s ($58). J. Crew’s Distressed Vintage Slim Jeans ($135) also lend themselves to rolling, as do Acne Jeans’ Generic Girl Tab Jeans, which are available in a light Stonewash ($299) or the darker OneWash ($269).

Photo of Katie Holmes, Splash News. Photo of Sarah Jessica Parker, Wenn. Photos of Rachel Bilson and Amanda Peet, Pacific Coast News. Photo of Reese Witherspoon, X17.

DISCUSS/68 post(s)

Designer Handbags

Posted by: sndgems | 2009-05-29 18:53:49

Armani Suits

Posted by: sndgems | 2009-05-29 18:51:24

Posted by: sam | 2009-05-04 16:00:25

good work. http://www.sndgems.com/

Posted by: sndgems | 2009-05-04 14:09:01

Trendy & Stylish. http://www.designerbrandsclothing.com/

Posted by: designerbrandsc | 2008-12-17 08:04:41

It is very interesting & stylish. http://www.sndgems.com/

Posted by: sndgems | 2008-12-17 08:02:34

Not so sure about those - a littel 70's aren't they? tanzanite http://www.lapigems.com

Posted by: Nicky_Jameson | 2008-10-14 10:20:01

I TOTALLY ♥ this look so relaxed a subtle chic not like the crazy BRIGHT colors trend

Posted by: jasmine | 2008-09-06 11:14:42

Tragic Trend. Witherspoon is the only one who kinda half pulls it off at least. What on earth has Bilson on her feet??

Posted by: Queen B | 2008-08-29 15:45:12

wwwd, i borrowed the image above, hope it's ok. thanks

Posted by: mirene | 2008-08-25 01:32:06

Reese witherspoon rocked this look, as for the others ESPECIALLY katie holmes, put it to rest, it looks dreadful.

Posted by: rachie8 | 2008-08-17 21:17:13

Honestly this is the type of thing that only a select few-- ie Rachel Bilson and Sarah Jessica Parker can pull off. Kind of a passing trend I guess? I dono.. I usually check www.shayblue.com to tell me what's in and there hasn't been anything there about the "frumpy chic". Hehe. Rachel Bilson is an amazing dresser though I'd love to know who her stylist is.

Posted by: Mandy | 2008-08-14 15:00:38

I actually think this trend has potential if it is done right. Katie and Rachel actually make it look cute.

Posted by: Anna | 2008-08-14 00:19:24

i think it is a potentially cute look. plus, it's great for us short girls who need to roll up our jeans cuffs anyway! http://www.whatagirlneeds.com.au

Posted by: chloeraina | 2008-08-12 23:04:34

um. this look is vile and tragic in every way. could reese look any stumpier? could katie look any more like a late-80's calvin ad? yikes. this is a trend that absolutely did not need to be resurrected. WWWD, you are actually moronic for making this post.

Posted by: kali | 2008-08-12 21:56:37

Please.This look is horrible.

Posted by: minos | 2008-08-12 13:51:00

Kate Lamphear does this perfectly! and has been doing the rolled up jean forever. She should have been featured! and enough with people trying to play editor by saying - you should only do it this way or that way, only with this jean...blah blah blah.

Posted by: klm | 2008-08-12 11:16:00

I feel like they're doing the look...well, just wrong. Shouldn't the cuff be rounded, not crisply ironed flat, ie. Reese. Karla, from Karla's Closet does it well with baggy jeans. Otherwise, this look is my favorite on skinny jeans right by the ankle--not mid calf! ie. Sarah... Visit my blog for more of my insights on fashion! http://omowrites.blogspot.com THANKS xo, S.

Posted by: Samantha | 2008-08-12 11:11:15

I LOVE THIS POST!! Thank you WWWD! I think the only one that knew how to pull it off the RIGHT WAY was KATIE HOLMES. She was the only one that kept it sophisticated.

Posted by: KOOK | 2008-08-12 10:09:00

I think I hate this "trend".

Posted by: SheShe | 2008-08-12 08:24:13

Even my 60-year-old mom does this! Have no idea where she got the 'idea' from. Maybe she reads my blog, hehe :) I guess this trend stems from Alexander Wangs fall (/summer?) collection and some other designers. Myself I got into this this spring due to my Miami Vice (the 80's show) fashion obsession. (I started to watch the show every day...)

Posted by: fashionlauncher | 2008-08-12 07:10:35

everyone needs to stop being so negative. if you don't like it, you don't like it. no one is forcing you to follow this trend or even like it! fashion isn't something that EVERYONE agrees on. That's what makes it fun. Everyone has their own thought to what they think is stylish and fun. If these celebrities think they look good wearing this trend, then let them wear it. p.s. katie holmes does look good though.

Posted by: blahhh | 2008-08-11 23:34:37

this is really. really. dumb.... direct yourself to DLISTED.COM to see how i feel about this "trend"

Posted by: littlelux | 2008-08-11 22:33:45

I guess Katie's started a new trend. I'm not sure about this certain style though, this is something I can't pull off. I have to admit, they do pull it off well. http://www.TheNaturalSapphireCompany.com

Posted by: Marilynn | 2008-08-11 20:34:37

good work. i love it.

Posted by: claudia olivia | 2008-08-11 20:32:38

rachel bilson is the only half decent looking one donning this "trend." i think the only way to wear this would be to roll up a slim jean. modishmouse.wordpress.com

Posted by: mt | 2008-08-11 20:23:53

Hmmm...I'm not going to jump on the band wagon with this one. This is one instance when just because celebrities are wearing it...that doesn't make it cute. I expect more from these fashion heavy weights. - Kathleen (theblackstiletto.blogspot.com)

Posted by: Kathleen | 2008-08-11 19:26:00

LOVE LOVE LOVE Rachel Bilsons shoe/booties they are just the cutest! Id have to say Rachel Bilson & Amanda Peet look the best

Posted by: Julie Newman | 2008-08-11 15:00:25

i love it! well i think they all copied karla of "karla's closet" blog fame. ;)

Posted by: Allison | 2008-08-11 14:52:28

Gotta say I love the rolled look, but definitely not the pegged jeans. I totally did this in the mid 90s with really baggy jeans, a big leather belt and tucked in t-shirt and then again in college in '00. Loved it then, love it now! Comfortable, funky and cool. And besides the pegging on Holmes, nothing about this really screams 80s to me.

Posted by: LuLuW-L | 2008-08-11 14:41:03

Funny, I just posted about this today too. The difference with Katie's jeans is she cuffed them in and up which is so 80's. I did it then and I hate to see it now. The straight rolled up look I can live with. Christina www.realstylerealpeople.com

Posted by: Reals Style Rea | 2008-08-11 13:36:25

let me tell you, I LOOVEEEE THE BF JEANS!! I saw a story on savvychic.blogdrive.com last week about where to find them cheap and went out this weekend and bought me a pair! They're so comfy and look AMAZING with heels and a fitted top!

Posted by: Amanda | 2008-08-11 12:26:31

I definitely think Rachel looks the best, the whole look really works for her. This is definitely a tricky look, but if it works, it looks wonderful!

Posted by: C | 2008-08-11 12:19:18

I like this look, it's just the celebs don't look that proportional. Like the pants are too baggy. I think if Katie Holmes' jeans were a size or 2 smaller than she'd look proportional.

Posted by: Laurie | 2008-08-11 11:53:48

I think this style is very hard to pull off. And these stars are not doing it that well. It's just an awkward length that makes you look bulky and short...

Posted by: roxy | 2008-08-11 11:45:11

I don't really like the trend, but congrats to Katie. I think soon everyone will be wearing her new shaggy hair look as well. It's funny how for the most part the sites only show frontal shots with this trend. With the girth of the jeans I'm pretty sure the back gives them a great diaper butt look. Oh yeah...sexy. LOL

Posted by: Nikki | 2008-08-11 11:39:29

I mean, it's kinda cute. a staple my mom has been wearing since the 90's. ...and isn't it just a bit too soon to be bringin' the 90's back? I dunno - but it looks comfy at least. I'm sure I'll be sportin' a pair soon...I still have my levis from the 90's.

Posted by: ...loveMaegan | 2008-08-11 11:20:20

Ugh. If this is the new denim trend, I think I'm going to stick to skirts! I'm having flashbacks to wearing my jeans like that in the early '90s with Timberlands and big scrunchy socks.

Posted by: K | 2008-08-11 10:54:14

I like this trend. I have not tried it yet. Actually I think that the bloggers pull it off much better than the stars! Check out my rolled cuff post that features two stars and two bloggers :) http://clotheslinefinds.blogspot.com/2008/08/whats-going-on-with-rolled-tapered.html

Posted by: anthea | 2008-08-11 10:53:57

the only look i like is rachel's- oh and i love conspiracy theories haha

Posted by: hoverboarder123 | 2008-08-11 10:36:17

This look is so unflattering. but i agree with pretty much all of you that Rachel Bilson looks the best. her pant legs are at least slim fitting! jeez the rest of them look like circus tents.

Posted by: alexiaa | 2008-08-11 10:23:54

i think they all look cute but reese looks the best. she is casual and easy. i bought current/elliott boyfriend jeans last week and i have worn them almost everyday since.

Posted by: P | 2008-08-11 10:21:22

my *daily style *blog: > fashionchalet.blogspot.com < Not big on this trend, especially the baggier styles. Cuffed denim can work, sometimes, when the denim fits you well; not over sized.

Posted by: Fashion Chalet | 2008-08-11 10:20:21

I thought Katie Holmes horrid jeans where from WalMart - little did I know you can get couture mom jeans for $385.

Posted by: Jenn | 2008-08-11 09:56:51

This just looks sloppy overall. However, if I were ever to roll up my jeans, it would only be w/ flats.

Posted by: meg | 2008-08-11 09:44:29

Since I rocked this the first time it came around in the late 80s, I stick to cuffing skinnies only, just above the ankle, with statement heels a la Bilson above. Everybody else looks a mess.

Posted by: MEP | 2008-08-11 09:44:20

not classy or stylish on any of these women. sorry.

Posted by: nicole | 2008-08-11 09:10:40

Ugh, I hope this doesn't mean it's becoming a trend! So unflattering and just.... yuck.

Posted by: helena | 2008-08-11 09:10:36

Rachel is the only one who looks cute. The rest jeans are unflattering they're too baggy and i can't get over that. i think tighter pants rolled up works better but only on skinny people (i couldn't pull it off) otherwise you look bigger than you really are.

Posted by: leah | 2008-08-11 08:58:16

I love this look, I wore it not to long ago too! and I've been dying to know what jeans Katie Holmes has been wearing. Thanks!

Posted by: klm | 2008-08-11 08:31:08

rachel looks good, i think like those kind of shoes and a shirt could make this work. www.thedailyalygator.blogspot.com

Posted by: alison | 2008-08-11 07:34:48

It's a cute look and a lot of French and Italian women are rocking it now . . . and they look great. (My boyfriend thinks so too!) A lot of people here are unnecessarily negative. Take the trends highlighted here as inspiration, not military orders -- nobody is going to come over to your house and force you to roll up your trouser cuffs! Geez!

Posted by: msliz | 2008-08-11 07:31:28

The only time I cuff my pants is when I'm on my bike. The look isn't flattering any of the women above, save for Rachel and SJP, both of whom stuck to the more fitted leg.

Posted by: Alison | 2008-08-11 06:58:55

I think this is a great casual look! Victoria Beckham also borrows David's Prps Barracuda Jeans and wears them a la Katie Holmes. And I'm LOVING Rachel's booties! Mega cute!

Posted by: Gillian | 2008-08-11 06:25:47

i love rolled cuffs but most of these are not the best examples on how to wear them. the jeans here are too oversize (except rachel and sjp). it looks wierd when you have a baggy jean and you try to make the ankle half the leg size. not attractive and probably not too comfortable.

Posted by: c | 2008-08-11 06:05:03

Gee, people here are negative about eveything. I think they look good. Fashion is not ment to be about making yourself look skinny. Sure they look very casual, Amanda Peet looks a little frumpy, but it's unique and I think a cute look. I really like Katie and Rachel's looks.

Posted by: Veronica | 2008-08-11 05:54:31

I just realised the last three comments were by Jennie, Jen and Jen (me being the last jen) IT'S ATTACK OF THE JENS.

Posted by: Jen | 2008-08-11 05:35:57

I find it hilarious, that celebrities diet to be size zero, and then make themselves look fat by cuffing their jeans. Nope you're not brainwashing me (as the fashion industry does...) to make me think this looks good in the slightest.

Posted by: Jen | 2008-08-11 05:34:25

Amanda Peet would look less ridiculous if she had both cuffs at the same length and maybe if she weren't wearing every current trend at the same time. It's too much, as the ladies over at gofugyourself so aptly showcased it. This trend is the classic example of seeing something so frequently that it starts to look okay and people start to follow along.

Posted by: Jen | 2008-08-11 04:27:07

Damn you, Katie Holmes! She's the leader in this questionable trend and it's amazing how fast it's caught on in the last like two weeks. yikes. totally viral as someone mentioned earlier. every entertainment site has Katie in these jeans, which she looks ridic in btw, but i do have to give her credit for having the balls to spearhead this trend and not giving a shit what anyone thought-and viola.. i knew it would only be a short matter of time before this trend would be featured here. i dunno, this late 80's early 90's fashion resurgence is quite questionable, imho.

Posted by: Jennie | 2008-08-11 04:22:05

Not cute. I'll stick to my basic bootcut and skinny jeans.

Posted by: Steph | 2008-08-11 04:20:05

Oh...my...god! You could NOT make jeans look more unflattering if you tried! This not only makes your legs look short, but fat too! I'd rather go around with "fashion victim" tatooed on my forehead. I think I might be sick...gag...

Posted by: P | 2008-08-11 03:21:12

Rachel looks good. The rest? Not so much. Love fashion but don't have the biggest budget? Check out this blog: http://wearfare.blogspot.com http://www.mostlymodel.blogspot.com - mostly models. 24/7.

Posted by: Wearfare | 2008-08-11 02:15:55

Yikes. I hate rolled cuffs. This affected, fashion-victim look is becoming so viral but here's to hoping it vanishes ASAP. It looks shlumpy and women should know better than to fall for these kinds of trends. All those clunky, dominatrix-style, aggressively strappy shoes are hideous too. Amanda Peet here for example is wearing both of these trends at once and, let's face it, looks like shit. Ask yourself ladies, would a guy find this attractive? Nope.

Posted by: JJ | 2008-08-11 01:00:45

ugh...no...this look makes legs look way shorter...not flattering at all...this is a very questionable trend...

Posted by: iadoreamore | 2008-08-11 00:54:28

love love love current/elliott. freshest jeans. so cute. i need to get my hands on a pair.

Posted by: pl | 2008-08-11 00:18:54

Rachel is the only one who doesn't look frumpy... www.indahclothing.com

Posted by: kianna | 2008-08-11 00:10:14

ARE YOU KIDDING? icky icky icky.

Posted by: Booglaboo | 2008-08-11 00:08:25