For the last couple of months I’ve been doing some community management work for Cherokee USA, which is a fancy way of saying I’m in charge of the stuff that appears on their Facebook page. For all my complaining about Facebook (seriously, would it KILL them to add an edit function? Does this not exist because of the fear that someone will post “I LOVE puppies, don’t you?” and 10,000 likes later, swap out puppies for “child pornography”? Because okay, that WOULD be sort of funny, not that there’s anything funny about—anyway, all I’m saying is I hate that I can’t fix a typo without deleting the whole thing and starting over), I’ve really been enjoying the gig. I’m basically just there to try and make the page a non-sucky place for parents to visit, so it’s pretty low-key and conversational—much more fun than the sort of corporate brand-bot weirdness where the writer attempts to pretend they actually ARE the product, not that I’m pointing fingers, BIZARRO-LAND MIRACLE WHIP TWITTER ACCOUNT.

Cherokee and Cozi have teamed up to offer up some Target gift cards to blog readers, and today I’m jumping on the giveaway bandwagon. I’ll get to that part in a minute, but just so everything’s all up front and tidy: not only is this a sponsored post, it’s sponsored by a client of mine. I’m just saying, if I was selling out any harder right now I’d have to launch an eponymously-named fragrance.

The general topic for the giveaway is back to school clothes—specifically, first day of school outfits, and how parents choose to capture the moment. This isn’t a subject I’m much of an expert on, frankly. On Riley’s first day I mostly looked for an outfit that wasn’t wrinkled or stained, and while I’ve seen plenty of inspiration for first day of school photos, I sort of phoned it in with a last-minute printed speech bubble:

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So I didn’t exactly knock it out of the park creativity-wise for his first day photo, but I think I’ll try this idea from Kim (aka Miss Zoot): I’ll take the exact same photo—same outfit and all—on his last day, too. Check out how Kim’s first day/last day photo of her daughter turned out:


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Cool, right? I would love to have a photo like that to see how Riley changed over the year.

I’m not super fussy about what he wears to school, but I do set out Riley’s outfit the night before. It makes things easier in the mornings, and also ensures that he’s not heading out the door in a pair of swim shorts with a Spiderman pajama top. My standards may be low, but they do exist.


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Here’s my question for you, if you’ve got an opinion on the subject: what do you care about more, your kid’s outfit for the first day of school, or their first school picture day? I see by our calendar that our picture day is on October 21st, and I suspect I’ll be in a tizzy the night before trying to find a photogenic outfit for his FIRST PICTURE DAY OMG. Hopefully they have a different backdrop than the Infamous PenisTurtle Theme of ’07.

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And with that unsavory image, on to the giveaway! The prize is a $100 gift card for Target, which you can of course use to buy a stack of new Cherokee clothes—or, you know, whatever else captures your fancy. To enter, leave a comment on this post (any comment will do, just be sure and include your email address). Contest ends . . . let’s say Wednesday morning, okay? Two days from now on the 21st.


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Good luck!

PS: there’s another big giveaway going on where you can win a $1000 shopping spree from Cherokee and a $300 smart phone from Cozi. Contest info is here.

PS part deux: if you’re a Facebook user, I’d be super honored if you would visit Cherokee’s page and maybe even hit that Like button—only if you want to! No pressure!—if you’d like to see my updates appear in your, uh, stream-hole.

*** Contest now closed, winner to be announced soon ***

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Melissa C
Melissa C
12 years ago

Love Target and love Cherokee!

Em
Em
12 years ago

I am going to remember these ideas for when my little one is going to school! Actually, I probably won’t. But maybe I’ll rediscover them when looking for ideas!

Jennifer R
Jennifer R
12 years ago

Yee-haaa Target!!!

Robin
12 years ago

I love the first day of school for so many reasons, and I still remember some of my outfits from when I was a kid. So when we get to that stage, it’ll be a big deal for us! (Well, for me at least…)

sienamystic
12 years ago

No kids, but growing up there was only one or two photos of “first day of school” – including one of me in total late 80’s gear, including a grey denim jacket, blue denim shorts, a carefully chosen casual t-shirt, hightops, and bangs with a ponytail. However, scattered around mom’s house are dozens of picture day photos, including the Year of The Bad Perm And The Geometric Cropped Sweater, Muppet Smile, and Good Girls Wear Plaid.

april
april
12 years ago

Ooh, I’d love to have this. With two boys, 14 months apart we go through a LOT of clothes. Also, can someone tell me how the oldest has managed to rip the knee out of the the left side of five pairs of pants? Why is it never the right side?

Amy
Amy
12 years ago

I was already a fan of Cherokee’s Facebook page and was excited when the light went off and I realized you were the one posting their updates (it took a picture of Dylan eating a popsicle for it to click).

I get more angsty about school picture day, because for me it really captures who he was that year. It goes in the school yearbook and I send it out to family, so I want him to look super cute (er handsome). I let him pick out his first day of school shirt. I wanted a nice polo, he went with a t-shirt that says “Hello I’m Awesome”. Oh well.

Stacey
12 years ago

We go shopping for a special “First Day of School” outfit for each kid (typically they end up wearing that same outfit for school pictures). It’s the rest of the days that I totally fail. I find myself standing in front of their closets on the second day of school thinking, “Crap! Now what are they going to wear?”

Sharon
Sharon
12 years ago

Wow, Riley is so cute. And so grown up!

megan
megan
12 years ago

Alas, I do not have kids (yet) but we will be trying once we are married (in April 2012!). In the meantime, I could sure use some new clothes….I have a safety pin currently keeping my pants from falling down around my ankles. I can’t just throw them away cuz the button part is the only thing that’s broken!

Alyssa
Alyssa
12 years ago

School picture day is this week for us!! I’ll put a polo and jeans on my boys. Usually they wear comfy pants and T shirts, just for ease in the morning.

Jill Browning
12 years ago

First day definitely warrants a new outfit, but I’d probably only buy a new outfit for picture day if I had extra money and my kid didn’t already have something new hanging in the closet. Thanks for the giveaway!

lisa alskog
lisa alskog
12 years ago

love giveaways!

Kristen
Kristen
12 years ago

Thanks Linda! Have a great week!

Amy
Amy
12 years ago

I let the kids pick their own first day outfits, and in a way I like those better than picture day clothes – their choices are a better representation of their tastes and personalities than the plain outfits I pick for picture day. I always take a photo on the front stoop before we head out, and love to compare them from year to year. (I put my foot down, though, and did not let my kindergartner wear a SpongeBob shirt on the first day. Second day, fine, just not the first.)

ErinFromIowa
12 years ago

We take a photo of first day so both outfits are important. I forgot about the turtle picture. Ha ha… oh my goodness.

Jessi
12 years ago

I love the idea of taking a before school year and after school year photo. I think both first day and picture clothes are equally important (ok, picture day more so).

Hannah
Hannah
12 years ago

Oh how I do not miss first day of school pictures in our front yard!

Junni
Junni
12 years ago

Ooh, pick me!

As a 29 year old with no kids yet, I have to say first day of school pics are funny to me. I don’t think my parents ever really cared that much, or maybe I just blocked it because of the trauma of the first day of school.

ANYWAY. My college roommate, as a joke our freshman year, asked me to take a first day picture of her to send to her parents. Then it ended up being something we did all four years. Now she has a little girl and has promised me that she’ll be sure to send me a first day of school picture every year. :)

el-e-e
12 years ago

What a great gig! Congrats on that.

We do a photo, inspired by some random co-worker, of the kid next to the school sign on the first day of school. He wears a uniform and it’s easy to compare and see the difference each year.

Stacee
Stacee
12 years ago

First day of school outfit, all the way, because it’s such a momentous day and will still be captured, by me, in photos that I always find more real and interesting and, well, relaxed, than the posed school photos.

jonniker
12 years ago

Any post featuring that picture of Riley is just the best thing ever. Poor Riley. But that photo is just so infamously epic. I love it. I do.

Michelle
Michelle
12 years ago

There’s a gallery of my school photos hanging in the hallway at my parents’ house. The only thing that people say about my pictures is “Wow, thank god for contacts, huh?”

BabyKMama
BabyKMama
12 years ago

I would say the first day of school outfit will be more important than school picture day (my son is 2-1/2). My school pictures always had one ponytail that had come loose… or my brother had a piece of hair sticking up… The first day of school pictures, we’re all happy and neat and clean, standing in front of the house with our new lunchbox. Those pictures have more ‘story’ to them than the school pictures.

Kelly
Kelly
12 years ago

heh. penisturtle pictures. :)

Ris
Ris
12 years ago

I still look at the pictures of the outfits my mom sent me to school in from those “first day” pictures and just cringe.

JoAnn
JoAnn
12 years ago

I am cheating, we have school uniforms so both outfits are the same and I have no say – yay!!!! Love love love the (cherokee brand, btw) school uniform!

Anne
12 years ago

I love the speach bubbles/signs – I never even would have thought of that. My own first-day-of-school pictures were just standing on the front step, no signs. I guess which year is which by how big my bangs were that year. Hey, it works.

Meg
Meg
12 years ago

I do care about 1st day outfit, but school pictures are way more important! I did a side-by-side first day/last day photo last year and hope to remember to do it every year.

Meghan
Meghan
12 years ago

The PenisTurtle theme never fails to make me laugh, even on days where I feel like I’m being forced to pose with a PenisTurtle.

elleana
elleana
12 years ago

I used to be anal about first day of school pictures, but now I’m just more concerned about them being showered!

Heather
12 years ago

Two-year class pictures – my darling man has chosen a daring ensamble – horitzontal striped shirt in muted fall colors, fire engine red gym shorts, socks that bleach no longer helps, and brown sandles. His mom (waves) totally forgot it was picture day. Let’s just say I stuck with the headshots.

Wednesday is his picture day, it is on every calendar I own.

Vicki
Vicki
12 years ago

Although I do dress my kids up for picture day, I secretly hope that one of them will make some type of crazy kid face on picture day. All the better to taunt them with later in life. :)

Linda
12 years ago

One of my 7yos is GRIMACING in her school picture and I hate it. I asked her casually what she thought of her pics (thinking OMG, RETAKES!) but she said, “I look like a ROCKSTAR!” so I’m stuck with a grimacing picture. It’s not worth arguing with her, IMO.

Jessica Larsen
Jessica Larsen
12 years ago

I remember when my sister put on (forbidden!) make-up right before her school pictures and thought my parents would somehow never find out….HA.

Deb
Deb
12 years ago

Oh, photo day all the way. I probably will forget to even take a photo for first day of school, but the photo day outfit, by definition, will be recorded for posterity. I don’t want to be the mom who has to listen to “What the heck did you dress me in that for?” comments. And it doesn’t matter how cool or lame the background is, my daughter will have a wan half smile and squinted eyes, and a completely stiff and self-conscious pose, so there’s really no way for them to turn out well. So at least she can be wearing a cute dress.

Abby
Abby
12 years ago

I love Target. :)

Chris
Chris
12 years ago

Riley looks seriously freaked out about that Penis Turtle. Bahahahaha…

I’m due with my first any day, I just can’t wait for all the picture days ahead of me!

Monique
Monique
12 years ago

When we are back to school shopping we usually pick out from the new clothes what will be the first day outfit. Now the middle one is in Standard School Attire (sort of a uniform – certain color pants, any solid color collared shirt), so whatever. Both girls dress decently every day, so I never stress over school pics, but I also never buy them either – with professional photographers as friends and family, I kinda don’t have to worry about that. But, love Target, need a card!

Sarah
Sarah
12 years ago

For Kindergarten, I think I might obsess over the first day of school outfit more. Just because it’s the first day of school ever. Starting with Grade 1, however, I’m sure Picture Day will take over the outfit obsession. :)

amy
amy
12 years ago

when james had his preschool photos done they did it after snack time…well, this is what i’m guessing since he had goldfish crumbs in his eyebrows. im preparing big time for the K1 pics with a nice retro puma tracksuit and a snack that will blend in with his brows if they choose to eat first…

MRW
MRW
12 years ago

I used to get worked up about photo day and then I realized my kid looks ridiculous in the school photos and I never buy any of them, so I stopped caring. We have tons of candid shots of him looking like he usually does, no need to spend tons of money for photos of him looking uncomfortable and irritated at being asked to pose on a stool or some other damned thing. My son picks out his own clothes and has for quite awhile but most of them are pretty generic pants, T-shirts, etc, so I don’t worry much about first day or photo day.

Kathy
Kathy
12 years ago

Neither! I think I’m in the minority here, but I let my son dress himself in whatever he chooses. His Kindergarten picture was awesomely awful, green shirt and brown shorts, it was so badly matched it made my eyes hurt. But I love that he choose it and I feel like as he gets older it will be fun to watch how his ‘style’, if you will, evolves.

Erica
Erica
12 years ago

I love Target and Cherokee

Bethany
Bethany
12 years ago

Oh, that photo of Dylan makes me laugh every time. Clearly first day of school photos can serve as a good backup should picture day go awry!

Elif
Elif
12 years ago

I think picture day as a lot of the family gets copies of that pic.

Peggy
Peggy
12 years ago

My first grader will not let me pick out any of her clothes. In fact, if I let on that I like something, it’s the kiss of death. She didn’t do too bad picking out her outfit on the first day of school. Picture day is this Friday already, so hopefully it won’t be a battle.

Stacy
12 years ago

Hmm, guess I should find out when school picture day is, huh? I don’t think I’m as worried about the outfit as the HAIR of my 5yr old girl…yikes.

cindy
cindy
12 years ago

My daughters are old enough (6 years old!) that they care about what they wear to school. I bought them new outfits specifically for their first day of kindergarten. Last year, at pre-K, they were sick on picture day and had to take pictures on a make-up day, which I didn’t know about beforehand. So…no cute school pictures from last year.

Merideth
Merideth
12 years ago

My mom was a teacher. She said she always felt sorry for the kids whose clothes were so obviously picked out by their parents so she always let us pick our clothes for picture day so i’ve just always done the same. I also like that if they pick it out the picture is a reminder of their “style” for that year.

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