7 school dropoff outfits that are comfy and stylish

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From a psychological standpoint, there are a number of reasons to get a little dressed up in the morning. Yes, it can boost your confidence. Yes, it’s a wonderful outlet for creative expression. While there’s nothing wrong with reaching for your go-to leggings and sweater, it can hard to break from what we know and love.

If you’ve fallen into an athleisure rut and want to switch up your daily looks, you’re in the right place. Below are some recent outfits I’ve put together that not only got me through the daycare drop-off but also through working from home, running errands and anything else my day had in store. The best part? These outfits take just as much effort to throw together.



Starting with an easy one. A jumpsuit can easily be dressed up with a cute bucket bag, classic loafers, and jewelry. Throw a sweater over your shoulder, and you’re good to!

Jumpsuit: Evereve
Sweater: Amazon
Bag: Anthropologie
Shoes: Madden Girl

Trousers and a denim jacket

The easiest and most comfortable swap you can make to your outfit is to switch leggings or jeans for a wide leg trouser. A denim jacket is a classic that’s always in style, as well.

Jacket: Madewell
Pants: Target (last season, similar pants here)
Tee shirt: Madewell
Bag: Clare V
Necklace: Banana Republic

Jeans and a sweatshirt

This is a cute and sporty look perfect for running errands. To make this feel modern, I have a cropped wide leg jean and tucked in the sweater to balance the proportions. I have a camera bag that sits right at the hip and a pointed loafer to elongate the line of the leg.

Sweater: Evereve
Purse: Target
Pants: Levi (old, shop similar style)
Shoes: Target
Hat: Clare V

Button down and jeans

I swear to you a button down is just as easy to put on and is just as comfortable as a tee shirt. I’m loving button downs this year. I’ve paired this long button down with a cropped jean and a crossbody bag to help create shape in the waist. Polish this with a loafer, and you’ve got an effortless look that can go anywhere.

Button down: Target
Tank: Target
Jeans: Pistola (old, shop similar style)
Bag: Target
Loafers: Madden Girl

Split leg leggings and a denim jacket

Ok, ok we could all use a stretchy pant day, am I right? I’ve elevated this look with a split leg legging, a button down and a denim jacket. Tip: roll up the cuffs to zhuzh this look up.

Button down: Target (old, similar style here)
Denim jacket: Madewell
Leggings: Amazon
Loafers: Madden Girl
Bucket bag: Anthropologie

Button down and jeans, pt. 2

Another way to style a pair of jeans with a button down. I’ve tucked this one in and draped a sweatshirt over my shoulders. I topped this outfit with a hat because somedays there isn’t much I can do to my hair.

Button down: Old Navy
Sweater: Evereve
Jeans: Gap
Hat: Target
Sneakers: Amazon

Jeans and a tee shirt

A shockingly easy outfit that’s comes together thanks to accessories. A braided belt adds texture, jewelry adds interest and the trench adds a touch of sophistication. Again, a hat. I just can’t with my hair sometimes.

Tee shirt: Amazon
Jeans: Levi (old, shop similar style)
Belt: Target
Trench: Banana Republic (old, shop similar style)
Loafers: Madden Girl