First-Day-of-School Outfit: MINE, Not His!

AHHH! This week my son starts school. As in KINDERGARTEN.  Elementary School. Big boy, “see ya later, Mommy… I’m too cool to sit on your lap even though I can’t wipe my own tush” school.

Yeah. That one.

I’m so nervous and so excited all in one. We have been quite concerned about his kindergarten readiness—should he be held back, should he follow the system as it’s meant to be… Fortunately, we found out he will be in the transitional kindergarten program, which means he’ll be in a class with children around the same age as him (if he went into traditional kindergarten he’d potentially be in a room with children who are already 6. He’s not even 5!) As a two year program, this gives him the opportunity to grow emotionally and developmentally.  And it’s free!!!

Hooray for public school and for redshirting!

But enough about him. Let’s talk about me.

First day of school. What does this mean? Cute outfit time! I can remember as a little girl spending the entire summer thinking about my outfit for the first day and first week of school. (This continued into college, of course). While it’s unlikely my son cares AT ALL about this, I know I certainly do. I’m not worried about him though. He’ll look fine. Adorable. Sweet. Like a real school-boy.  Me??? That’s the concern. (Oh, how I love my narcissistic ways).

First of all, there will be pictures. Lots of pictures…. Pictures that will not only be cherished for years and years to come, but, let’s face it, should be darling enough to generate a ton of likes and comments on Facebook (After all, how else do I know if my life is good?) Second, I’m meeting not only the teacher, and want to make a good impression, but I’m meeting other parents –complete strangers—who I will hopefully forge friendships with and will hopefully approve of me so that in turn they encourage their child to be friends with mine. (That is how it goes, isn’t it?)

SO, I’ve come up with five possible outfits for the first day of school. Keep in mind, a) we’re walking to school b) It’s 945 thousand degrees and c) I was alone during this little try on session so I had to take pictures of myself. Which I’ve confessed, is the only way I can tell what I look like these days. 

Okay, Here we go!

OUFIT #1: Striped Maxi

This is a light cotton dress from J. Crew. I’m not sure it’s the most flattering dress I own but it’s obviously hot weather friendly and summer-y yet on-trend. Not sure I want this dress though in pictures for years to come though. Thoughts?

OUTFIT #2:  Bright Jeans with Bright Top

We all know I like my bright blue jeans. I'm thinking this is a casual, cute look. The bright colors seem happy unlike the Death Star chic look I’m going for in #4. 

OUTFIT #3:  Sheer Blouse with Shorts

I think this is my favorite of them all. Considering that the pictures are mostly for my benefit (at least I’m honest), I like that the shorts  (from J Crew) will show off my leg, BUT I’m covered up on top. You like?

OUTFIT #4: Black Sundress

This One-Star for Converse, black, with eyelet details from Target is certainly comfortable and I think (for the price point), pretty cute. But I’m worried it looks like I’m in mourning. Let me rephrase: I kind of AM in mourning, does this give it away?

OUTFIT #5: Workout Clothes

Nothing says, here’s the real me more than my Lululemon pants, my sports bra, and Mossimo tank. Let’s be honest, as a mom who works from home and works out in the mornings,THIS is the outfit that I will most likely be wearing at drop offs (… and pick ups). I’m thinking I should call a spade a spade and wear the outfit that the teachers and parents will most likely identify me with.  I mean, it’s almost like a safety precaution really.  Agree???

Fortunately, all of these outfits have one thing in common: They’re completely comfortable, cry proof, and will be fine without mascara. Holding back the tears now!