5 Days of Drop Off Outfits: 2019 | Olive and Tate

5 Days of Drop Off Outfits: 2019


Just the other day, a fellow mom at preschool waved at me and said "I always know it's you because of your red scrunchie!"

Oh, the red scrunchie. I use it to hold my hair up while I wash my face at night, manage to fall asleep in it and then don't bother to take out prior to running my kids to school? Yep, that would be me.

While I'm never going to be one to really pull myself together prior to my babes waking up in the am, I do have to walk Georgia in the morning and need to walk to the door to pick up Gray in the afternoons, so whatever I slap on my body to head out the door will be seen by the general school public. And apparently, they've been seeing a lot of my hot mess hair. 

So, for the second year in a row, I put together a school week's worth of comfy outfits that either feel like pajamas or actually are pajamas. This year is even more fun because I'm teaming up with my friends Britt at Southern Mama Guide and Sarah at Sarah Tucker, so be sure to check our their drop off outfits too! Each outfit should be easy to toss together with little effort, will get you through multiple seasons and are appropriate for public viewing!

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Here are my stats: 
5'9", DD, 8-10/29 in bottoms, M/L in tops


Literally, this is my dream outfit. Comfortable (pajama level comfortable), slimming, hides coffee stains, and put together. Don't be surprised if you see me wearing this one on repeat!




Sweatshirt (wearing a medium for a slimmer fit): simple, easy, inexpensive and comes in a ton of colors! I wanted a slimmer fit for layering so I sized down in this sweatshirt. 

Joggers (Large): I snagged this exact pair on sale during the Nordstrom sale and the sizing is now super picked over. Here are the updated version from the brand and a similar pair at a much lower price point.

Jean Jacket (Large): My jean jacket is from this post, snag another jacket that I own and wear here.

Sneakers (TTS): I live in these slip on sneakers (light pink option here) thanks to the comfort level and slip on style, making the cost per wear more tolerable. Similar pairs here and here

Bag (similar, mine is old): Nothing link the cross body to keep your hands free! Two similar looks for lower price points here and here

Sunglasses: I own this pair in three different colors - black, tortoise and the amber! 


While I am wearing a pair of jeans with this outfit, please feel free to swap out that pesky denim with a pair of leggings. If I'm being honest, that tee and leggings combo is one I would sleep in so throwing on a cardigan that feels like a blanket and slip on sneakers will take approximately 30 seconds of effort. 




Sweater (Medium): I love the emerald green shade of this sweater but it does come in neutrals if that's more your speed! It's soft and roomy, promise you'll wear it constantly. 

Long Sleeve Tee (Large): I love the "luxe" line at Old Navy for non-clingy, soft basics. I don't need any tee to cling to my mid section, so the cut and flow of the luxe line is a fave. 

Jeans (wearing a 10): Fair warning, these run a little snug but will stretch with wear! Black jeans are, for me, a quick step up from leggings, so consider yourself dressed up in this ensemble! 

Sneakers (TTS): easy to slide on in a soft shade of grey - perfect for running out the door! 


Jeans and a few strategically placed layers can fool even the sharpest eye into thinking you are 1. wearing a bra and 2. had all of the time in the morning to pull yourself together. Little do they know...




Jacket (Large): the one thing I wear in my closet more than anything else: my field jacket. I own a camo and an olive green version, nearly identical to this one. It's the perfect layer to keep you warm and hide the fact that you're not wearing your bra. 

Sweatshirt (Medium): It says "Good Times" which is ideal for a morning with babes, right? It's soft and cute, size up for a roomier/more traditional sweatshirt fit. 

Jeans (10): distressed but with a slim leg, this is great pair to have on hand. I thought these ran a bit snug, so size up if between sizes (I think it's the feel of the "Power Straight" denim, it's supposed to hold you in just right!)

Slides (TTS): I love a woven slide, for me, they're a bit more put together than a flip flop but just as comfy.



I could live in this look. This is similar to the first outfit but with less of a sneaker look, a tank knotted for definition and cleaner joggers (no pockets). It's a perfect look at how you can take basics like the sweatpants and jean jacket and wear them other ways to flesh out that drop off wardrobe! 



Jean Jacket (Large): a classic jean jacket will always be a wardrobe staple for me. I wear mine year round. 

Tank (Large, knotted by me): The luxe collection makes another appearance in a tank! I prefer the regular neck and not the high neck but the fabric is so flattering and soft. It's the perfect tank to knot over the waist of the jogger, creating definition in your waist line and adding a little fun to the look.

Joggers (Large): simple, comfortable and a slimmer fit. I couldn't ask for more.

Slides (TTS) 



This outfit is ideal for colder mornings - the sweatshirt is fleece lined and oh so soft! 


Sweatshirt (shown in XL): You've seen this sweatshirt before! I own it in two colors and two sizes, love it and live in it. The cut is shorter and more fitted than a traditional sweatshirt so I've sized up in the one pictured for a roomier fit. The button detail features working buttons and the inside is lined with fleece! 

Leggings (Large): snagged these on sale during the Nordstrom sale and truly feel this brand is worth the splurge. The rise and fit are truly flattering and the emerald green tone is just a step away from black while still changing things up. I found a dupe here

Sneakers (TTS): tired and true with a pop of color! 

And a bonus outfit, complete with red scrunchie


Tank (Large): I own this tank in 4 colors because it has a built in bra! It's the perfect layering piece but I do wear it alone in the summer! 

Leggings (Large): oh yes I did buy these in a two pack on amazon! 

Sweater (Medium): mine is sadly sold out, but I've found similar dusters here and here

Happy Carpooling! 


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