Style File 08.15.11

jcpenney contacted me a few weeks ago, to see if I was up for a style challenge: To create a look inspired from a back to school photo from my childhood. I loved it! I knew exactly what picture I wanted to use as soon as I read the email…


Haha. Little Jen. Isn’t that dress so cute? I thought it was the perfect starting point for creating an outfit that was updated and modern. I chose to use the chambray fabric as my starting point. I found this AWESOME Mango Chambray skirt at jcpenney and paired it with my favorite blouse from J.Crew. I am pretty excited with how it all came together.

I may not be heading back to school again this year to teach, but something about the end of August always makes me want to get some new “back to school” items in my Wardrobe.


Outfit Details:
Blouse: J.Crew
Belt: Thrifted
Mango Denim Skirt: c/o jcpenney
Socks: Cut tights
Wedges: Forever 21
School Bag: c/o Lulu’s

one more…


I would love to hear about your previous back to school looks. What was your favorite? Your least favorite? Any super embarssassing ones?



  1. oh back to school, such a terrifying time … I remember once wearing this off the shoulder white puffy sleeved shirt … man did I love it but now when I think of it I cringe …too funny, I haven’t though of that shirt in a real long time! I love your back to school outfit, the belt is perfect!

  2. My most embarrassing back to school outfit was in sixth grade. I wore a red t-shirt and plaid jumper while (to a new school!) while all the other girls were in Debbie Gibson t-shirts and cut-offs. So embarrassing!!

    Looking back, it was actually a pretty nice outfit … I may have to do a recreation this fall!

  3. I love how you used an old photo from childhood as your inspiration!

    My Kindergarten first day of school outfit sticks out the most in my memory. Excited to be going to school, I had my grandmother buy me this black and red plaid skirt, with mini-suspenders embroidered with little apples, and a white shirt with an apple on it. I guess I had to dress on-theme!


  4. My mom had me in saddle shoes from the moment my feet could fit into shoes (I was a premie) and they remained a staple until i finished 4 or 5th grade. I would always joke around with my mom about the love for these shoes, ironically i came to love them and am so happy they are back in “style” in my adult years. I cannot wait for a little girl of my own so i can buy her a pair to send her off on her 1st day of school.

  5. I went to catholic school for 8 years so besides going to the Army and Navy store to get our uniforms we also had to go shoe shopping. I have many fond memories of my mother taking me to Payless and trying on what seemed like hundreds of shoes before like always going back to the same staple year after year: saddle shoes!

    Other than that it seemed like I was always getting a new hairstyle the first day of school. In Kindergarten my mother and I were really into hair crimping which led to a school photo of me looking almost like a burn victim. In first grade she cut all of my hair off and if I weren’t wearing a jumper I would look exactly like my brother.

  6. My favorite back to school outfit was the outfit I wore on my first day of kindergarten– crazy colorful printed shorts, neon pink sneakers, and a white tshirt with a very prissy looking cat screen printed on it. And my bookbag was neon orange and green. Definitely not the most stylish outfit but I love it because it reminds me of the early 90s and that my mom always let me wear whatever I wanted, regardless of how utterly ridiculous I looked.

  7. awww, love the photo of you running off the school bus, super darling. i can almost smell the crisp fall air! i love first day of school pics.

  8. Love this photo challenge! I actually had a chambray top with rainbows enbroidered on the sleeves that I wore for 5th grade picture day—adorable! It was the first year I remember being excited about clothes and carefully planning my hair and outfit. Unfortunately, my kitty scratched me across the cheek the night before! (Of course something like that would happen to me!) Even though I had a huge scratch mark, I still remember thinking “at least my shirt looks good!”

  9. Least favorite back to school (now in retrospect) was my entrance to middle school (7th grade) covered in Abercrombie & Fitch logo-ed monstrosities. Cringe worthy now, to think about it.

    Favorite? 11th grade when our school enforced a new dress code (just black pants and white collared shirts) and I got to wear a 50s vintage white peter pan collared shirt and black skinny cigarette capris, a la Audrey Hepburn.

  10. I love how translated the little outfit to the big one! Chambray and leopard is a favorite mix of mine.
    I remember my very first day of kindergarten I wore a red white and blue tracksuit. It was 1996 and the olympics were huge, so my mom thought I should go looking like a little olympian. Unfortunately, It did not help me out when gym class started.

  11. My parents would always forget to take pictures on the first day of school. I have about 10 years worth of second day of school pictures. I can’t remember any specific year, but I usually wore some sort of floral dress that was very 90s. I also remember that for kindergarden I got a turquoise pocohontas lunch box and I thought it was the world’s greatest accessory.

  12. Going back to school was one of my favorite days of the entire year. I loved it when I was old enough to pick out my own outfit…in high school it was usually jeans and a sweater from Abercrombie. Things have changed a lot since then! πŸ™‚

  13. Oh boy, there is a picture of me that’s straight our of Little House on the Prairie, pigtails and all. Thank goodness we wore uniforms most of the year.

  14. Chelsey •

    The only back to school look that really sticks out in my mind is one from 9th grade and 12th grade. In 9th grade I wore this red and navy striped polo type shirt with a white collar with some very dark denim jeans and red flip flops. I had my hair chopped off to my ears. A lot of people asked if I was a lesbian. I just chalk it up to being in an “awkward” phase. I didn’t really know what my style was then. It’s more defined now, but I’m still working out the kinks.

  15. Being Home schooled I never really had a back to school outfit, though my favorite outfit to wear is different weekly and depends on my mood.

  16. I remember my freshman year of high school. I wore a striped tank top, jean shorts, and brought a purse. This was the first year that I wore a purse, so it was definitely memorable!

  17. Hillary •

    Cute pictures! I like the concept of re-doing your favorite back to school outfits as an adult.

    My favorite back-to-school outfit was probably for my first day of Kindergarten. My mom had sewn me a really cute little blue and red jumper-dress that she had appliquéd yellow hearts and dinosaurs onto. It sounds goofy, but it was actually a really adorable little dress. I also had red ribbon barrettes in my hair.

    My least favorite was definitely my back-to-school outfit for my first day of middle school. It was some ill-fitting black corduroy overalls, ugly clunky shoes and a shirt that was way too tight for me! Ugh. Middle school was so painfully awkward!

  18. Sheena D. •

    I wore the very large pink frame glasses for my vision, I don’t know that those were ever cool, but I just had to have the pink frames as a little girl…

  19. I think my most embarrassing school memory was probably the year my school photo featured my almost toothless grin. I had lost maybe four teeth all at once? haha. of course the outfit I was wearing didn’t help much. Oh 90’s fashion. haha

  20. On the first day of kindergarten, I wore a pepto-bismol pink matching skirt/sweater with little flowers on it. I had pink/white saddle shoes to go with it. I LOVED that outfit.

  21. Oh how I miss the days of spending a week agonizing over what to wear to make the best first impression…haha maybe not! πŸ™‚ I do love dressing up and finding the perfect “special-occasion” outfit…I cringe when I look back on all my mix&match bicycle shorts outfits. The horror!!

  22. i grew up in the 80s. there were lots of embarassing ones. like the jean jackets, with jeans. really, little sarah? really?

  23. In grades 3 and 4, I used to wear the most horrible crushed velvet turtlenecks to school. It was a real shame.

  24. in 4th grade I had the WORST fuzzy purple shirt. it was like a carpet! Oh the horrors of the first day of elementary school! haha

  25. You’re too cute in your kid pictures… and your adult ones too ;P

  26. I don’t remember any of my back to school looks…probably because I’m the 6th kid and there is no photographic evidence!

  27. Love that outfit. I’m definitely going to check JCPenny for that skirt! It looks just like a (much more expensive) Madewell version I’ve had my eye on. For some reason, a pair of pastel plaid overall shorts that had a matching bowtie stands out as one of my favorite outfits from preschool. I just remember loving wearing that bowtie (probably don’t want to recreate that one now, though…)

  28. Shannon •

    On my first day of high school I wore all red, a red skirt and a red blouse. It might have been a good idea if I hadn’t also been badly sunburned, and was therefore red too. Oh well. Great giveaway!

  29. I was home-schooled until my senior year in high school. I still remember what I wore the first day of my senior year though. Jeans, white polo and flip flops!

  30. Felicia •

    My most embarassing first day of school outfit, didn’t involve the clothes I was wearing. The week before I started 2nd grade, I begged my mom to get me one of those fake makeup sets. On the first day of school, I went to town! lol.
    Looking back at the picture, I look absolutely ridiculous. White cheeks, pink lipstick, bright blue eyeshadow, but boy was I proud!

  31. When i was 7, I got a yellow sweatshirt with an embroidered parrot on it as part of my back to school wardrobe. In hindsight it was hideous, but at the time I thought it was the best thing ever.

  32. I loved planning my back-to-school outfits! I think my favorite/most mortifying was 7th grade… I had jean shorts with rainbow beaded trim, which I paired with a red hooded tank top. So awesome.

  33. my absolute favorite back to school outfit was this light blue dress that had clouds all over not sure why but i loved that thing. it seemed like i would wear it everyday. =]

  34. I really don’t remember any embarrassing looks specifically, but there probably were some. I remember having a pink & white polka dotted bag for my first day of kindergarten though – I kind of wish I still had that bag.

  35. Aww, you look so adorable!! I love your grown-up take on your back to school look–that skirt IS gorgeous! I remember being so excited to wear new fall clothes, like Dr. Martens and a plaid kilt.

  36. I still remember my first day of kindergarten! I went to private school, and we had 2 jumpers – blue & pink. I wore blue, and some nasty girl bully told me I couldn’t play because I wasn’t wearing pink! Rude! Hahaha.

    I LOVE your back-to-school look! πŸ™‚

  37. Super cute outfit Jen!! Back to school outfits are always so fun!

    I think my favorite thing to wear was new shoes. Even if I didn’t wear brand new clothes, it was always nice to have shiny new shoes on the first day. That and having new stationary really made me excited!

  38. This is so adorable!!! I always ended up wearing something with patterned biker shorts, mismatched socks and jellies… aka super embarrassing forever. I loved back to school shopping though (and usually did it at jcpenney!) and always very meticulously planned my outfit for the first day of school WEEKS before school actually started. That, and buying new school supplies were the only things I loved about going back to school haha

  39. I remember being in 9th grade, going through this punk rock phase thinking I was the coolest thing ever. I had a pair purple pleather pants, a black fishnet shirt with a black “corset” tank top. Oh and black combat boots. Totally not my style these days, but I still thought I was the coolest thing ever.

  40. i think my classiest outfit as a kid was when i had to do this “giant” oral presentation in 2nd grade. my class got chosen to read stories that we wrote as a creative writing project; mine was about my favorite teddy bear that got stolen. ANYWAY, i was wearing this red plaid powersuit- it was a plaid blazer with embellished gold buttons and a black miniskirt that looked separate but was totally attached. finish off the look with nude tights, black flats, and a perm that could kill. i was a hit.

  41. gotta love my first day of high school, in head-to-toe American Eagle in different shades of purple. Thanks, trendy high school kids!

  42. In my first grade picture I was rockin’ the tucked in sweater with suspenders. To top it off I had the sideways ponytail and thick bangs. i was pretty cute if I do say so myself. πŸ˜‰

  43. I always dread looking back at the turtlenecks and suspender outfits my mom so adoringly put together for me in my elementry school days. She put a lot of thought and money into those outfits at the time, but looking back even she’s got to see how terrible they were! lol

    I always wonder how the outfits I’m going to LOVE putting on my daughters now will mortify them when they’re older, lol

  44. On my first day to kindergarten I wore my school uniform (red plaid jumper) with my hair in two braids. I remember this outfit the most because my mom took a picture of me on the driveway with my backpack. I look cute but super goofy!

  45. LL Bean rubgy shirt and Gap jeans, perfect back to school look in the 80s/ early 90s! Thanks, hope I win.

  46. i had a body glove t-shirt with tons of flourescent colors on it. i wore it with matching flourescent shorts and my brand new hot pink, silver, and black l.a. gears (with four layers of laces). i’m hoping this year’s back to school will be just as fun with a more refined color pallette. πŸ™‚

  47. omg i am dying. you look so so cute.. way back when and now!!!

    <3 steffy
    Steffys Pros and Cons

  48. brilliant giveaway, thanks for the opportunity! back to school outfits were never my strong point. i recall a particularly awful matching blue striped polyester pants and turtleneck that did nothing to make my new bowl cut look better (grade two). yikes.

  49. There is a photo that exists somewhere in this world….first day of fifth grade….
    acid wash overalls with only one buckle done, a green tshirt with the sleeves that folded up to reveal purple, some brand new adidas kicks, and the perm that my mom made me get every year. But in this photo, the flash made my perm’s shadow huge. FROTASTIC.

    I’m much better now, I swear….

  50. I love the grown up look you did! I too love back to school time and sometimes whish I was still in school so I could go shopping! I love this time of year. ps. Rowan is sooo adorable!!

  51. Mine. was. AWESOME.

    For my first day of kindergarten, I was sporting a red tunic-y blouse with white fringe across the front, white leggings, and white cowboy boots with sparkles. I looked pretty sharp.

    …come to think of it, minus the fringe, that may not be a horrible outfit nowadays either…

  52. My favorite is my kindergarten picture. Not only did I insist on dressing myself for picture day (pretty sure I’m the only kid whose parents allowed that, but, hey, hippies for parents. What can you do?) but I would not take the picture unless my stuffed rabbit could be in the picture too. I was ridiculously stubborn even when I was that young!

  53. Hehe….going into 6th grade, I wore this horrible 80’s outfit. It was black stirrup pants with this long black and white button down that had some silver in it too with one of those elastic belts! My bangs were teased too! Thank goodness style has changed since then!

  54. In first grade, my favorite ever dress was a floor-length number with a white lace empire waist top and a pink skirt with red roses and a HUGE ruffle at the bottom. This was 1976, so I was SUPER stylin’. ;o) Also, I was a rowdy child, so I played on the monkey bars, played kickball, and ran around like a maniac in that dress. I wore it to death, literally.

  55. So cute! I love that you kept the socks too. It is funny how the exact same style can look so modern now!

    I love those last two pictures of you in the raincoat. You were one stylish little kid!

  56. I think my least favorite school outfit was any of them I had to wear tights with…I ALWAYS came home with rips and holes in my tights….it was a HUGE source of frustration for my mom…hahahahaha! Ironically , I ADORE wearing tights and leggings now…:-)

  57. the first day of 6th grade my mom thought i looked sooooo cute in this matching top and capris but, this was years before capris were even “cool” to wear. i felt like a freak of nature. not only did i have a matching outfit on, people looked at me like my pants were too short PLUS it had an insane mix of miami vice and golden girls pattern going on. from that day on, i started telling my mom she could not dress me anymore.

  58. The only first day of school outfit I can remember is first grade. I wore a pair of green floral shorts that ended up being belted around my waist because I was to skinny for them to stay on, and a matching green shirt.

  59. my kindergarten teacher to this day remembers me as the girl with really cute dresses who came in from recess with scuffs and scratches everywhere! i’d start school with shiny shoes and go home with scuffs haha. i was too adventurous for dresses. πŸ˜‰

  60. What a great idea! I would have a hard time finding New Kids on the Block t shirts to recreate my elementary school looks!

  61. You did such a good job, I love the updated version – especially the socks!

  62. I have a great one where I am holding a my little pony and I literally have no teeth in my mouth. its adorable!

  63. oh my word. that bus picture is a-mazing. love it!

  64. So cute! I remember one fine school pic with neon lights in the background. Yay 1980’s!!

  65. My favorite back-to-school outfit was my very first day of kindergarten. My grandma had gotten me an adorable navy blue sailor dress with red trim. I remember the square collar had red embroidered stars on it – I loved that dress! My most embarrassing came when I was dressing myself. The first day of middle school, I wore an ankle length blue skirt with a princess-style yoke in the front, a military-style button down shirt, and lace-up brown boots. A total mish-mash of what was “in-style” for the time… such a mess! Not to mention the badly permed hair :).

  66. I have a picture that I’m wearing suspenders, I’m missing my two front teeth, and I have a huge band-aid on my chin because of my stitches. It is such an awful picture.

  67. There are six girls in my family, and all of us wore the same sweatshirt on each of our very first days of school. It was red and had apples, scissors, and blackboards all over it. It’s fun looking at all the different pictures of each of us wearing it.

  68. My favorite back to school look was a super 90’s jumper with Tweetie Bird high top Convese sneakers and stick on earrings (remember those?)! Awesome!

  69. i used to have these huge round glasses that had pastel rainbow frames and from the day i got them in 1st grade to the day my brother stepped on them in 4th grade, i loved those things. looking back now though, i was such a 90’s child. every school picture with those glasses and a big scrunchie in my hair- how did i make friends? ha

  70. I went to Catholic school from K-12. My favorite back to school look ever was my cranberry plaid jumper, a yellow oxford with a pair of Bass gum shoe nubuck oxfords and yellow socks! I wish I had gotten to pick out awesome new clothes for school each year…though the uniforms made dressing easy!

  71. In third grade I had a new yellow dress to wear the first day of school. Another girl wore the same dress in red. We ended up best friends for the remainder of our elementary school years πŸ™‚

  72. My mom’s favorite color is purple (it wasn’t mine at age 7 – nor was it ever for that matter) and she bought me this head-to-toe purple sweatshirt material outfit that she was so excited for me to wear. Needless to say, that was my first day of school outfit and I looked and felt like an eggplant. The next year though happened to be my favorite back to school outfit: a pair of overalls that I decorated myself and a floral shirt underneath with MATCHING FLORAL SHOES!

  73. My favorite school outfit was one I wore for picture day in Kindergarten. I wore a black skirt with a white turtleneck with a striped vest on top. I also wore a red headband and leggings along with patent leather mini heels that were adorable.

  74. Lindsay •

    Oh boy! My grandmother sewed me vests when I was young. I was so excited about them, but can’t believe the pictures now.

  75. I rocked a pretty righteous bowl cut with some pink osh kosh overalls for first grade, which might be my favorite. Although I did also have a sweater that had giant scotty dogs on it, so it’s a tough call, really.

    I love the way you updated your outfit, you look so great!

    Lauren @ See Parrot

  76. Natalie •

    I used to love to be matchy-matchy. I remember getting a purple shirt with Koala bears on it and finding perfect leggings to match at another store!

  77. This post is so awesome! I have some pretty horrible back to school outfits from the middle school ages. But my little kid ones are awesome! I’ve looked back on some of those old pictures and been like – man, I would wear an adult version of that right now! You did a great job reinventing your childhood back-to-school look

  78. Ah, fun — love your back-to-school blast from the past! Back in elementary school (the early 1990’s), I was fond of t-shirts with pictures of cats on them, often paired with some vaguely matching shorts (or, even better, a skort — remember those?). So my best back-to-school outfit was in the 3rd or 4th grade — a cat t-shirt, magenta skort, canvas slip-on shoes (like the ones they’re selling at urban outfitters now, surprisingly), and a SIDE PONYTAIL. I thought those were the coolest. This also coincided with the time in my life when I wore giant blue eyeglasses, so there was lots of awesome going on.


  79. Amanda S •

    I never got to have an office back to school look.. because i wore uniforms from k-12th grade… but each year in grade school we couldn’t wait to see who had what shoes…In 6th, 7th, and 8th grades the shoes became a popular item for us girls to express ourselves.. However in Highschool we wore the same everything.. even the same shoes… so we had to think of other ways to be creative.. Unnatural colored hair and purses were not allowed.. so it came down to jewelry and hair accessories to bring life to your uniform. I must say though highschool was the best time because it was an all girls school we didnt have to worry about dressing up for boys.. it allowed me to make amazing friendships that i still have today!

  80. The only back to school outfit I really remember is the one I wore to the start of grade 4. I wore a grey-blue tee shirt with a cat wearing sunglasses on it, and bright pink shorts.

  81. Oh man, I had these purple leggings that I was obsessed with! I wore them with a slouchy gray sweater on the first day of school in 3rd or 4th grade (and I bet I even had my hair in a side ponytail!).

  82. i don’t know why but for some reason i felt the need to dress up in a really weird fashion on the first day of high school every year. so for my first day of sophomore year i decided that electric blue tights & knee high blue/green striped athletic socks under daisy dukes was a great idea… especially when i decided to wear cowboy boots and a bright orange tank top.

    like…. what?!?!? it is VERY embarrassing to think of….

  83. Rebecca T. •

    I remember zip off cargo pants were totally cool when I was in elementary. I mean pants that could be transformed into capris and then shorts with just a zip, genius! πŸ˜›

  84. This is soooo cute. You were a beautiful little girl, and your take on the modern-day version of your back-to-school outfit is spot on. I have that exact same Mango skirt from JCP and plan to remix throughout the rest of this summer and through the fall.

  85. Oh yeah, I meant to add that back-to-school for me always sucked. I always had hand-me-downs and the worst I can remember is having to wear S.A.S shoes (i.e., cafeteria lady) shoes in like the 5th or 6th grade … sad, I know. Thank God for new beginnings, though πŸ™‚

  86. oh my goodness, i absolutely LOVE the idea for this post! and the old photos of you are the most adorable things ever!!! πŸ™‚ XOXO

  87. Breanne •

    Would love to win! My fave back to school outfit ever was a black and white polka dotted skirt with a black and white striped top. Even in fourth grade I was pattern mixing!!

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Hi, I'm Jen!

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