5 Days of Drop Off Outfits | Olive and Tate

5 Days of Drop Off Outfits

Oh, friends. Do I have a story to tell you.

If you follow me on Instagram, you may have seen this pop up in my stories but today's post is inspired by a harrowing tale of yours truly needing to go into our preschool when I hadn't planned to. And by "hadn't planned to", I mean I forgot my 4 year old's soccer jersey and had to run home to get it, head back to school and hand it off to the school director. I did notice that her eyes flicked down below my neckline for a quick second, which is when it occurred to me that, since I was still in my pajama top, that I wasn't wearing a bra. Hoping that I wasn't exposing too much to the woman in charge of guiding and molding the minds of my young children, I hopped back in the car, pulled down my mirror and realized that not only was it very, v.e.r.y. obvious that I was not wearing a bra, I was also wearing a tee shirt from the very back of my drawer that proudly states "Mimosas Made Me Do It."

mmmhmmm. 

So, with that in mind, I decided that I was slacking a bit on my preschool drop off game and needed to make sure that I had easy, warm, comfy outfits on hand that could either be pajamas or layered right on top of my pajamas as I ran out the door. Yes, I could put on real pants like jeans or a shirt with buttons, but this is about being prepared and meeting my life where it is. And where it is looks something like a boozy tee shirt and exposed mom boobs.

I hit the mall and in just about an hour, I put together a school weeks worth of outfits that are perfect for those first moments of public viewing - at the bus stop, your coffee run or, hell, for the entire day. I'm going to share how I put the pieces together, my sizes and how to wear it with other pieces in your wardrobe. And you are welcome in advance for my hair and no make-up, I just wanted to make sure it was easy to visualize my entire drop off "look"!

Let's get to it:


5 Days of Drop Off Outfits


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Leggings I slept in make for the perfect base layer and since it's gotten chilly overnight here, I'm doubling down on sweaters. The crew neck knit runs small in the chest so make sure to size up for the ladies (I'm in a large and need every inch of it).

Wanna wear it again? Layer the sweater vest with a white v neck tee and distressed jeans plus a bootie, pair the crew neck sweater with faux leather leggings and live your best life pretending to work out in those Amazon leggings

5 Days of Drop Off Outfits


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I love this grey sweater coat - it also comes in cream and truly covers a multitude of sins. It runs very large so size down (I'm wearing a large in the photo but should size down to a medium). The tank is soft and flowy around the midsection and perfect as a base layer or pajamas and the pair of flats is one that I buy every single year. Last year's pair was navy and this year, I went for the blush.

Want to wear it again? I can't think of an outfit that wouldn't benefit from the sweater coat but think it would be especially cute for a date night with ankle length pants and a lacy tank.

5 Days of Drop Off Outfits


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Hello, jeans with an elastic waist band, you are perfect. Distressed, dark wash, a hem on the ankle length side - and a soft, stretchy middle - so easy to pull on and feel like you've tried, you know. I love the shape of this over sized/boyfriend sweatshirt (and no, not just because I could hide my pajamas under it!) and it also comes in a tunic length. The grey sneakers are in my cart, they just rolled them out in store and didn't have a pair to fit my size 9.5 hooves but rest assured, they'll be coming to live with me soon!

5 Days of Drop Off Outfits


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I can't stop thinking about this coat because it feels like a down comforter. I mean, if I have to roll out of bed at least I can roll into a coat that feels like my bed, you know? If I had owned this coat last week, I could have zipped it over my braless, brazen tee and saved myself the embarrassment. It is on the cropped side in the very center but runs TTS, I'm wearing a large in the photo. If you haven't tried on a pair of Spanx leggings, just go ahead and give them a go, just to see. I'm a fan and own them in both the faux leather and traditional black versions.

5 Days of Drop Off Outfits



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This sweater comes in a range of super cute colors and is just so darn soft. With jeans and a flat, it will go anywhere, but with leggings and sneakers, it's taking me to Starbucks before I even bother attempting to get my life together. I'm in a large and the neck could be a bit low cut for some - just layer it with the tank you slept in and you're all set! Check out the navy version and imagine for Spring - it would be amazing with jeans and sandals. What can I say, I'm always here to justify your long term wardrobe choices!

Ok mamas, now go forth and drop off with confidence, knowing that at the very least, you won't have to explain your booze themed ensemble to the school ethics council.....

6 comments

  1. Love these suggestions! I now have several items in my cart to buy.

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  2. Thanks for all the great suggestions! Drop-off sure has its challenges. You did Lorelai Gilmore proud!!

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  3. Everything looks so cute on you -- not sure I could pick a favorite! Love that orange sweater for fall, though.

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    1. Isn't that the best shade of orange?? It's super soft too, so a complete win! xo

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