What to wear on the first day of school

Nikki Parkinson Beauty, Fashion 29 Comments

Tomorrow my youngest starts school.  The first day of 13 years that will ultimately determine what he will be when he “grows up”.  I’ve done this day twice before.  I do not get any better at it.

I’m excited.  I’m nostalgic.  I even start to fondly remember him as a tiny baby.  (In my wistful dreaming, I am only thinking of the times when he was sleeping and I had had a full night’s sleep.  Not when he – and I – were screaming like banshees.)

Mr 5 is pumped.  There is no other word for it.

Mr 5 is pumped for his first day of school

Me, I’ll be the one sobbing uncontrollably and needing counselling (aka a wine with lunch) as I wave goodbye.

Mr 5’s starting school also presents a wee problem for me  … remembering what to wear for the drop-off and pick-ups.  I’ve been out of this loop for years (teenagers do not want you ANYWHERE near school at all. Bless their hormonal- cotton-school-regulation socks).

Most mornings, I’ll have a client appointment after the drop-off, which means I’ll feel incredibly over-dressed.  And feel to the need to explain my over-dressed state. 

On other mornings – my work-from-home blogging days – I’ll be running the tricky fashion tightrope of comfort versus style. 

In both scenarios there is the added time pressure that a school morning brings.

To make it easier for me – and you – I’ve put together some secret weapons you’ll want to have on hand to get you through the first day and beyond.

1.  Mineral makeup is the key to you achieving a flawless face in seconds. Try Jane Iredale PurePressed Pressed Minerals SPF 20 at Adore Beauty ($83)

2.  I wear regular mascara every day. I only use waterproof mascara on certain occasions.  The first day of school is one of those occasions.  At the moment I’m loving Napoleon Perdis Mesmer-Eyes Waterproof mascara at Napoleon Perdis ($35)

3.  I feel naked without at least a slick of lip gloss on my lips.  There is ALWAYS about three in my handbag.  This is one of them: Lanolips Lip Balm in Rhubarb at Addicted 2 Lip Balm ($13.95)

4.  There is only so much that waterproof mascara can hide.  If in doubt, call in the big guns – oversized sunnies to hide first day tears and all manner of dark, puffy eye sins.   Quite loving these Christian Dior Two-tone Catseye (RetroSun) on sale at HoneyHoney (were $284, now $198.80)

5.  Slip out of your heels in the car and into some ballet flats if, like me, you find yourself having to dash your child up to the classroom and then dash back to the car and on to a corporate meeting. These will go with any outfit: Sambag Tina Musk/Grey Printed Snakeskin Ballet Flats at Sambag ($175)

6.  A large proportion of my wardrobe contains little or no-iron clothing. Some people call them lifestyle clothes.  I call them save-my-lazy-ass clothes because they always look good without any effort on my part.   A dress is the simplest solution. I have this dress in black.  I think I need it in raspberry as well. MiMi FiRST Gathered That dress at MiMi FiRST ($129)

7.  I have all my accessories hanging in clear view and I always add at least one before stepping out the door.  That statement necklace can draw a lot of attention away from teary eyes and you will always feel more “put together” with it on.  I have my eye on this one: Large Vintage Silver Indian Tribal necklace “Harper” at Table Tonic ($159)

8.  If your small child is, well, small, there is a fair chance you’ll be carrying their bag for them.  A small handbag you can sling over your other shoulder will prevent you from having to do the keys/phone shuffle, thus also preventing said phone falling to ground and smashing into a gazillion pieces.  This bag is so beautiful, yet practical:  Mimco Constellation Mini Hip at Mimco ($279)

Have you got a child starting school this year?  What do you wear for the drop off and pick up duties?

Comments 29

  1. Very swish indeed. I like the no-iron save-my-lazy-ass clothes, they match my “haven’t sleep properly in 8 months” bags under my eyes. This kid better sleep before school!
    Thanks for you comment today on Kerr-Boom! Glad you had a quick birth 🙂

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      I have it in black – and have been wearing it almost weekly (because of no iron factor!)for about a year. It works perfectly for a work casual day – and look just as good with flats as it does with heels or wedges.

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  2. I was dragging along a 3 year old and a 1 year old aswell as my son to school this morning, so comfort clothing was the choice of the day (as well as being about a billion degrees). Shorts, thongs, a dressy-ish top and some make up were good enough for the teacher meet and greet.

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  3. Love what you’ve suggested. Yes, this will be the year where all of my kids will be in school! YIPEEEEE! My third will start prep and I cannot wait…but yes I will miss him too…What I wear at drop offs/pick ups? Well, casual clothes really and I steer clear from any gym wear unless I was actually going to do some exercise. Nothing wrong with wearing them, just that it makes me feel all lazy when I do! Winter it’s jeans or pants, during the warmer months I would wear the staple capris, skirts and sometimes even sun dresses…yes I do love to dress up, just not over the top. The only way that will make me feel all refreshed and not drab, even if I was to just drop them off to school. 🙂

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  4. Love all your picks. The dress and necklace are stunning! My son is in grade two this year, and I have my 16mth old in tow to do drop offs and pick ups. I make a effort to look decent lol but comfortable as well. I love my cardigans and jeans!

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  5. Yes!
    My son starts kindy next week. He did preschool on the school grounds so I have some experience of the drop off/pick up. My son’s school is yummy mummy central, so I am trying to balance looking halfway decent (I don’t want to be the chubby Helena Bonham Carter of the class) and not overdressed for the things I do after dropoff – take younger child to playgroup, gymbaroo etc.
    As I have said to my husband, I am not trying to compete, just trying to maintain my dignity. Does that make sense?? Love the dress above!

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