January Jones in Hipster Drag

Posted on January 16, 2014

BREAKING: January Jones is a hipster douchebag.

Not really. We just liked typing that. We hope it comes up in a lot of google searches. But we have to admit, if we encountered a guy wearing the top half of this look:


“Mad Men” star January Jones does some shopping in West Hollywood, California.

We’d probably roll our eyes and mutter “Pfft. Hipster douchebag,” in a voice only the other one could hear because that’s a super-power that couples gain when they’ve been together as long as we have. Also, the “I know exactly what you’re thinking right now but let’s shelve this conversation until later” telepathic exchange in the middle of a social setting.

To be honest, we kind of love this look on her. Sure, it helps that she’s model thin and actress pretty, but those jeans are currently her Best Friend, and we love the accessorizing, with the kickass shoes and the pop of color in the bag. Obviously, we could’ve done without the hat but it we have to admit, it brings the whole look together. This is real style. Maybe someone else put it together for her, but it’s perfect for her, completely thought out, and looks great in pictures.

We are going to get an epic amount of disagreement on this one, aren’t we?





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  • That outfit can sell purses.

    • MK03

      Seriously, how cute is that bag??

      • Chickadeep

        I am all about that bag. The bag and the sunglasses are the only things I want from this outfit, but I *really* want them. Okay, I lied. I want the signet ring, too. Meh on everything else.

      • GeoDiva

        I can’t make out the label, who is it?

        • Nicole

          It’s a British label, Smythson! I found pics of her carrying the same bag on another site that ID’ed it 🙂

          The style is still available (Eliot mini tote) but, sadly, that color seems to be sold out.

  • kipper

    Hey, we have all had the JGF munchies … she looks great.

    • lexilexi

      JGF munchies… good one kipper!

      It must be really warm down there in January, January. I’m in Northern California, and this is an August look for us.

      • NinaBoo

        It is ridiculously warm here. It’s been in the 70s-80s for weeks. We now have fires starting and that ain’t good.

        • lexilexi

          I am sorry to hear that, NinaBoo. This is not good on so many levels. When will it rain????

          • Magatha

            Hey, lexilexi, I’m in Northern California, and this outfit would work in our afternoons lately. (Micro-climates?) Soon as the sun gets low, brr, but damn, it’s been very dry 70 degrees in the afternoons. I would love to see January wearing some some chic January raingear, but it looks dry dry dry. But JJ looks cute and chic.

          • lexilexi

            Magatha, I’m on the Peninsula…. let’s lobby for TLo to come to the less-hot part of California – the NORTH!

            Where are you?

          • Magatha

            Just north of San Francisco, (TMI ALERT!) where everyone is wealthy, privileged, hipper-than-thou, self-indulgent, blah blah blah, and yet somehow they are still nice to me, a modest spinster who walks their dogs, house-sits, and does odd jobs and errands. It’s real beautiful here, and I gain huge advantages by being rich-adjacent, even though my IRA got nuked from orbit several years ago. Life is good, and I wish other non-rich people were as fortunate as I am. I am now gonna go out on the deck where I am house-sitting and wave in your direction. Cheers!

  • E2_Remote

    Stylish AND functional, she’s ready to come over and whitewash my fence when she gets done shopping!

    • Magatha

      She could come over, but she’d never pick up the paintbrush on account of the Tom Sawyer effect.

  • PlethoraofBooks

    Nope – I love it. The perfect Sidewalk/Street Style.

  • jspark

    It’s all about the shoes. From the side it almost looks like she has tiger feet.

  • Andrew Schroeder

    This is hardly hipster.

    • Trent

      Agreed. Also, serious question: as a guy who’s been buying and wearing vintage Trilby hats since the mid-80’s, it hurts me to think that TLo would call me a hipster douchebag if they saw me wearing one. Is this the prevailing opinion? ) :

      • fnarf

        I feel your pain. It’s definitely a problem. The douchebags in their crappy hats they bought at the airport are ruining hats for everyone.

      • SugarSnap108

        FWIW, I don’t believe that hat=default douchebag. It’s just that a lot guys with a douchey aura seem to wear them, for some reason. When a hat truly fits a guy’s overall style and personality, I like ’em.

        • Trent

          That makes me feel a little better, thanks. So when, say, Justin Timberlake wears one of his many fedoras, does he get a pass?

          • SugarSnap108

            Heh, Timberlake gets no passes from me. But some ‘normal’ guys I know wear a fedora well. My guess is, if you’ve been wearing vintage hats since the ’80s, they suit you.

        • Munchkn

          Whew! My not-quite 5 year-old granddaughter came over the other day wearing a fedora. She’s not a douchebag! She said it was her cowboy hat.

          • SugarSnap108

            I feel comfortable assuming your preschool granddaughter is, indeed, not a douchebag. 🙂

  • LeelaST

    I like everything but the shoes. Love chunky footwear but not *shudder* wedges.

    • Vaniljekjeks

      I’m pretty much your opposite. Could leave the outfit, but LOVE the shoes. Wedges are my best friend as a tiny person who also enjoys being comfortable while wearing heels.

      • I used to dislike wedges myself but then something hit me upside the head like, DUH!, wedges are the alternative to heels. And I’m not a fan of heels. So…now I like wedges. There are so many cute and stylish wedges out there. I mean, I still (begrudgingly) rock heels every now and then but I’m definitely on Team Wedges.

    • 3boysful

      I love these shoes! But I’m wondering if they take half an hour to don or remove due to the many little buckles?

  • czarina

    What’s the deal with only tucking in the front of the t-shirt?

    • Slanted & Enchanted

      Is that not normal? I’ve been doing that for…I guess the time that belts have been out of style. Pretty common amongst my friends as well. Now I’m wondering if I’ve been living in a post-apocalyptic bubble where humanity has lost the ability to correctly tuck in t-shirts.

      • KinoEye

        Belts are out? *Looks down at belt holding up jeans* Darn! I like the front tuck, though.

    • Adrianna Grężak

      That’s been a trend the past year or so. I think the logic is that baggy blouses are popular, but look like a tent if you have any sort of bust. The funny thing is, it reminds me of how all the girls tucked in the front of their giant t-shirts for gym class. …in middle school …in 2001.

      • I absolutely LOVED tucking in the front of my baggy gym shirts into the gym shorts. Good ol’ days.

      • mlle

        That’s exactly why I do the front tuck. All the girls in my middle school gathered and knotted their oversized shirts in the back.

    • In_Stitches

      I think it’s to keep the leg lengthening effect and line that one gains from having an unobstructed view of all of one’s pants coupled with the un-stuffy appearance of an untucked shirt.

  • mmebam

    I wouldn’t consider this hipster. I would consider Anne Hathaway’s style more hipster.

    • Rhonda Shore

      The fedora brings it into hipster territory, but otherwise it’s LA cool. I also like that she’s recycling a holiday shopping bag. She looks fabulous!!!

      • mmebam

        I get that, but the rest of the outfit is pretty LA chic. Hathaway, on the other hand, would have the Fedora and the kicks and the ironic oversize tee and probably a shake from Jamba Juice for good measure.

      • Since she’s at a farmer’s market, she probably got the bag from a recycling vendor.

  • OMM4

    Those shoes! Can anyone ID? Mama want.

    • decormaven

      Yes- I couldn’t wear them IRL, but they definitely could earn a spot in my fantasy closet.

  • Glam Dixie

    I guess I’ll disagree because I hate those shoes and the hat makes me want to smack her, the jeans and shirt are ordinary.

    • kimmeister

      I dislike any shoes that make feet no longer look like feet.

  • Maryanne525

    I should try the All White Diet. I’d be too terrified to eat a single thing wearing this. CLEAR LIQUIDS ONLY.

  • charlotte

    No disagreement here!

  • Denise Alden

    I can’t help but love JaJo, and I think she looks great. Except for the t-shirt. Too flimsy and thin, and kind of crappy looking. However, still love her and this look.

  • I mistrust women who wear white jeans.

    • Anna

      I mistrust outfits I can’t eat lasagna or cheeseburgers or sundaes with extra chocolate sauce in ;).

      • That’s why I mistrust them. People who have grubbiness-avoiding superpowers might also be able to steal your internet banking passwords with their mind.

      • kimmeister

        Whenever I wear my cream wool coat, coffee cups spontaneously commit suicide in its presence.

        • Anna

          Ha, same with me with anything in the pale spectrum. Whenever my “big day” arrives, I need to find a wedding dress that’s the same colour as my favourite foods.

    • kimmeister

      *Looks around furtively* I’m a fan of a well deployed white jean. Nina Garcia is over the moon for them in her book i just finished.

    • siedhr

      I love white jeans with a dark top. Really sets it off.

    • I’m mostly just jealous of them. My thighs and white jeans are not friends.

      • formerlyAnon

        Sub hips for thighs and I’m with you. Which doesn’t mean that I didn’t wear ’em, in the day. But I starved to do it and still didn’t get the look I [very unrealistically] wanted.

      • kimmeister

        It’s more about the cut and the weight of the fabric than the color though.

        • While I agree in theory, I’ve yet to find the white jeans that don’t just make me feel sad.

    • conniemd

      White jeans are for people who are rich enough to throw the clothes away after wearing them only once.

      • Jackie4g

        What you might try is buying white jeans or pants at the end of the season. That way, when Nature (or some klutzy person), takes its course, you don’t feel nearly as bad. There is something really rich girl and chic about a dark top and white jeans.

  • @Biting Panda

    No disagreement outta me. Werqing that store run.

  • Amanda

    Lose the hat

  • Introspective

    im not in love. id steal the purse in a second. but the shoes dont feel quite right. i scrolled down wanting some other kind of kickass footwear than these.

    top feels like nothing we bks dont already own, but in an unremarkable 2 for $25 kind of way.

  • MzzPants

    A perfectly good shopping outfit for a girl who’s not on set.

  • Laura Renee

    Nope. She’s gorgeous.

  • Diego!

    She is selling hat, sunglasses and shoes. Her shirt is hideous and that white jean is about to display a camel toe. I like all the black stuff here. The rest is kinda meh…

  • Anna

    Like the accessories aside from the hat, rest of the outfit is pretty bland. Which I suppose does suit January Jones. To a tee, in fact.

    • Blair Sylvester

      haha i caught that. thanks for the chuckle

      • Anna

        Anytime 🙂

  • ailujailuj

    THE SHOES. make it. looks great.

  • kimmeister

    I hate the shirt so much. Shades, bag, and jeans are fine.

    • Whollyholeyholy

      I just can’t deal with the shirt and jeans together at all. Clearly I’m in the minority here. I chose to pick on the jeans, but you’re right. That shirt looks like it came from Walmart.

  • KateMaryC

    My kingdom for a belt.

  • siedhr

    I usually (mostly) agree with you guys, but not today. I find the whole outfit to be bland, personality-free and lacking any thought. How do you end up with a bunch of basic pieces that don’t work with each other? How? It’s like she snatched random pieces from different outfits. That shit is UGLY and looks cheap. The jeans clash with it. The sandals are boring and too heavy. The bag doesn’t match anything. All topped with a meh hat. The Ugly hurts my soul.

  • Jean Beaton Leavitt

    I hope this is the beginning of the end of giant handbags.

    • alyce1213

      Fingers crossed. I mean, everyone needs a tote now and then, but does every bag have to be enormous? So clumsy and hard to get around. The stupidest part, when I see them pictured here on this site, or even on the street, is that they always look empty.

  • formerlyAnon

    She can get away with it, and on gals who can it’s a good look. Not a huge fan of the shoes, I’d prefer something more truly casual, but that would probably have lost her Style points.

    [TL;DR ALERT: The following ENTIRELY related to my own issues/triggers in my youth, and I feel compelled to type it but y’all are more than welcome to skip it.]: Nonetheless, I object to this in principle on the grounds that curvier and heavier women who are going to try for this look are doomed to frustration. They are gonna look like girls with hips, and turning into underweight skeletons (the solution of choice for sadly many) isn’t going to fix that.

  • Not from this kitten. She is hipster LA perfection personified.

    • Imasewsure

      That’s true… go to Jerry’s Deli on a Sunday and probably half of the restaurant looks like this… and that’s just the Valley!!

  • Jessica Freeman

    Its really the shirt I hate. The rest I’m on board with.

  • BendinIntheWind

    I’m loving everything here BUT the top. Too flimsy and boring and it doesn’t add anything to the outfit. I’m ok with the all-white, but find a top that’s a little more interesting and less ratty-looking.

  • The shoes and the hat make the look. The purse isn’t that big a “pop” of color, unless you consider any color being a pop of color against an all-white ensemble.

  • Kate Andrews

    I like the hat and sunglasses a lot.

  • tallgirl1204

    My main reaction was “Who wears shoes like that in real life with those clothes?” My second reaction was “What woman with a little baby/toddler wears all white?” Clearly her life is not like mine. Cute outfit, but not one for a mortal.

    • formerlyAnon

      Yah, the Venn diagram for “all white ensemble” and “caretaker for baby/toddler” only intersects in the movies.

  • teensmom99

    I’d be okay if the hat fit.

  • Denise Rambo

    I’ve never seen her wear anything nearly as nice as Betty Draper’s wardrobe.

  • estella_nyc

    This looks like something Sarah from the band Phantogram would wear, minus the hat, which means the title of this post is spot on.

  • Jennifer Peters-Ahnberg

    Not from me. She looks great here. I really wish I had skinny feet. Shoes that amazing never come in wide sizes.

  • MissFern

    she looks like a hipster santera.

  • sweetlilvoice

    I’m just jealous that she can venture outside without a coat. It’s snowing here…again. I think she looks cute!

  • Imasewsure

    Just hate the hat. Love everything else although something more would probably be needed (Hey Jan… how about a scarf?)

  • Whollyholeyholy

    I cannot get on board with the all white. Blue jeans, black jeans, jeans in some jellybean color. And if I *must* accept all white, then I need it to all be stark white and not that eggshell on the jeans.

  • Missy

    She looks good. And she also looks like a female version of Alexander Skarsgard here. Methinks this is not coincidental.

  • KSpence


    (I’m speaking only of the “Happy Holidays” bag. The rest of what’s going on there is cute.)

  • Inspector_Gidget

    Love it! She looks so good when she’s not self-consciously trying to circumvent the Betty Draper costuming.

  • Slightly butch lady in white wins the day.

  • BridgetK

    I have raging weather jealousy because of her sunshine filled situation. I’m wearing a shirt like that (under 3 other layers).

    Also, she looks super cute. 🙂

  • boweryboy

    The shoes seem to be out of place with the rest of it. I would’ve liked it more if she wore a pair of beat-up Chucks instead.

    • formerlyAnon

      (I agree, but I tend to have more of an east than west coast sensibility, I may not understand the subtleties of LaLaLand fashion.)

    • MilaXX

      I don’t mind the shoes. For January the shoes ring truer than chucks ever would.

      • boweryboy

        I agree with you on that, but they seem so incongruous with the rest of the outfit which reads casual day out.

        But since she’s sending off a hipster vibe, and I live in a hipster staturated Pac Northwest city, most women I know who dress similarly would pair this with some beat up Chucks or Toms.

  • MannahattaMamma

    Those shoes are from hell, which is clearly where she got the hat. I hate that hat thing. It doesn’t keep the sun off your face or your hair out of your eyes; she’s not a man in “Mad Men” or a man currently living anywhere in Brooklyn, so WHY THE HAT? (I won’t even ask why any living human would wear shoes like that. To the store, no less. puh-leez)

  • MilaXX

    No disagreement from me. it’s hipster drag, but the look works. It’s cute.

  • It’s ok, but honestly that hat is giving me shades of Britney and no good can come of that.

  • Qitkat

    I irrationally love it all. Really cute bag, anyone know whose it is?

    • Nicole

      (Reply from below) It’s a British label, Smythson! I found pics of her carrying the same bag on another site that ID’ed it 🙂

      The style is still available (Eliot mini tote) but, sadly, that color seems to be sold out.

      • Qitkat

        Found it! ‘Only’ £995. Sigh, when pigs fly.

  • In the shade you can see how different the whites are. They seem to clash. The shoes would be more fun in a color. Or even a brown? I like the texture of the tshirt (what is that called again? triblend? slub knit? something?), but it is just so boring to do white with white unless it’s with more sophisticated, dressier pieces.

    • demidaemon

      I just wanted to say I LOVE your user name. Whoo, Gundam Wing!

  • kim bunchalastnames

    no disagreement here. she looks put together.

  • Nancer

    I want those shoes!!!

  • BKagainwiththesweatpants

    White pants are Satan’s playground. But I loooooooooove the shoes.

  • marlie

    She looks absolutely adorable, BUT, this screams July in LA, not January in LA (ha).

  • uprightcitizen

    You can’t be a hipster douchebag unless you’re a guy? I beg to differ! This is a great outfit for a skinny girl at Whole Foods, but her hat is either too small, or not on her head right. Stingy brims, porkpies, and other small fedoras need to sit down on the forehead, whether you’re male or female. When you wear them on the back of your head like this, you’re simply wearing them wrong, and it contributes greatly to their douchy-ness. Personal pet peeve, and mostly only committed by celebrities for some reason. Maybe it’s true that that they all have enormous heads?

  • fnarf

    She looks magnificent. If you don’t like this I will fight you in the street.

  • frannyprof

    No disagreement here. Since we’re experiencing summer in the middle of winter here in SoCal, she looks great. Did I mention that the weather here in L.A. is fab right now? Perfect book-signing weather?

    • formerlyAnon

      Clever clogs. Slipping that in like that.

  • susan6

    Nah, this isn’t hipster d-bag. The shoes, hat, purse, and jeans keep it out of that classification. You want hipster d-bag, check out the guy at my university who sets up a hammock using a tree and a railing in the middle of campus and proceeds to chill out in a highly public way. Look at that f**king hipster. (Because that’s what he wants you to do!)

  • H2olovngrl

    That t-shirt is the part of the equation that I cannot abide.

  • Jacqueline Wessel

    It used to take years and years to get a tee shirt to look that ratty. And now you can buy them already beat up. I am bemused.

    • alyce1213

      It’s a process called burn-out, where the cotton is treated to create a sheer pattern. The t-shirt is thin, soft and looks very weathered after one wash. Not expensive — I got one a couple of years ago.

  • Gatto Nero

    No argument from me. Everyone should be allowed to wear a ratty tee shirt once in a while, even in public, and even if they’re famous. And the shoes, shades and bag — c’mon! She looks kinda great.

  • ThaliaMenninger

    I like the sunglasses. That’s as far as I’m going. The asshat is not my friend.

  • CPK1

    i love everything but the shoes. They make her feet look oddly truncated. They are better from the side. From front they remind me of orthopedic footwear.

    • Eric Stott

      I agree- the outfit reads casual, but the shoes say contrived.

  • I love it. She is an ice queen divine, even on the way to the grocery store. The shoes are the perfect punctuation for those pants.

  • I love everything here. It’s not fair to comment negatively on a celeb who’s out running chores. Redcarpet – yes…me time – no.

  • suzq

    The hat = my hair sucks today and you really don’t need to see it. Brilliant.

    Yes, that bag is gorgeous.

  • GillianHolroyd

    Trying. Too. Hard.

  • kerryev

    Yes. Those shoes are the sissiest badass I have ever seen.

  • jjjoy

    “this is real style”. really? she’s wearing basic pieces and none of them are that exciting individually or together. she looks douchey, not hipster.

  • Closet Crisis

    If some anon girl walked down the street like that… sorry, nope. she looks slovenly and the kick ass shoes and bag only serves to highlight the ratty tees and not quite white jeans.

  • bellafigura1

    I think she looks great because I would wear that (not the shoes so much, I would fall over) but I’m curious about you guys saying someone else put it together for her. Her street looks demonstrate a lot of savvy, but also fundamentally true to who she is — not styled at all, just very her.

  • Those shoes are killa. They make the look.

  • KT

    I love it! She looks super cute, and it doesn’t even look like she’s trying. Nicely done.

  • CatherineRhodes

    These hats are everywhere in Los Angeles right now, so it doesn’t even read hipster douchebag to me. More like that is so 15 minutes ago….

  • PeaceBang

    Just want the bag. A LOT.

  • lrhoff

    Really? This is a good look? No, cannot get on board with it.