Back-To-School

These first-day-of-school dresses are perfect for every style.
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20 First Day Of School Dress Ideas For The Perfect Photo

Pick the perfect dress so they feel ready to tackle that first day.

It may have been years since I had a first day of school, but I can still clearly remember the exciting feeling of being able to start fresh. The crisp, sunny days of September make it feel like anything is possible, and for many kids, starting anew means a a great wardrobe as well. The first day of school outfit is almost as important as a backpack stocked with schoolwork essentials, and first day of school dresses tend to make a big impression.

A brand new dress can make the first day of school feel more like a celebration and less like something to dread — a lot of kids will be excited to show off their new dress to all of their friends and their teacher! Putting some thought into what they wear during that big day (or even that whole week) can really help change their mindset.

Of course, that doesn’t mean you have to go out and drop a boatload of cash on a fancy dress. There are tons of options out there for every budget and every type of kid, and we’ve rounded up some of the best. From classic and traditional to trendy and casual, there’s something for everyone.

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1

A Striped Dress

This colorful striped dress is playful and bright. The tank makes it ideal for warmer days, since the first day of school is often still hot, but it’s also a good length. And, personally, I love the ruffled bottom!

2

A Summery Tank Dress

Cute and summery, this tropical inspired tank dress will make them feel like their summer days aren’t far behind. This is easy to throw on with a pair of sneakers and will keep them comfy all day.

3

A Denim Classic

You just really can’t go wrong with a chambray dress like this one. It’s a classic, it goes with every accessory, and it’s nice and casual. It can also be layered over long-sleeve tops when the weather starts to get cooler.

4

A Printed Twirl Dress

This strawberry print dress is so cute and perfect for the end of summer vibe you’re going for —but if strawberries aren’t your thing, it does come in a few other fun patterns. The tiered skirt at the bottom makes this spin out in the most fun way when they twirl (hence the name), and it comes in a wide variety of sizes.

5

A Tulle Dream

If you have the kind of kid who wants to get more dressed up for their first day, then a tulle skirt dress like this one is a must. The tulle instantly makes it feel more fancy without looking over-the-top, and it’s still functional. I personally love the little dog on the front that it makes it super playful.

6

A Comfy Option

For sporty kids who want to wear a dress but still feel like they’re in their comfort zone, there’s this sweatshirt dress from The Gap. The pink and blue tie-dye is a fun print, and the comfy sweatshirt material makes it very wearable. Keep in mind this won’t be ideal for first days that are very hot.

7

A Chic Wrap Dress

This white wrap dress is for ages 6 to 14 years, yet it manages to look more chic than most things I personally own? The wrap style is comfortable and trendy, and it’s a great lightweight option for warmer days.

8

A Romper/Dress Hybrid

Some kids love dresses, it’s just that dresses weren’t exactly made for their very active lifestyle. Enter the romper/dress hybrid: it’s basically a romper with a skirt over it, so it looks like a dress, but is as functional as shorts. It’s perfect! This one is so cute for the first day impression.

9

A Cute & Simple Option

Toddler moms, this Carter’s dress is so cute for the first day of day care, nursery school, or preschool. The sweet ruffled details make it feminine and fun, but it’s also nice and simple.

10

A Fancier Dress

This extremely sweet pinafore dress is definitely a bit more dressed up than some other options, but if that’s your child’s aesthetic, then this is perfect. From the embroidered flowers to the tiny white polka dots, this is hand-me-down material.

11

A Dress & Headband Set

Another adorable toddler option is this simple but sweet ribbed dress. It comes in three different color options and goes up to age 4, and I love how easy it is to throw on no matter what the occasion. The matching headband is a big plus! Mori makes incredibly soft clothes out of 100% organic cotton, so this is an all-around winner.

12

A Dress & Scrunchie Set

Available in sizes 5/6 up to 15/16, this dress is great for older girls. It comes in three different patterns that don’t feel too immature, and the ruffled bottom is a nice touch. It also comes with a matching scrunchie for a good hair day as well.

13

A Tie-Dye Maxi

Everything’s fine, it’s just that this girl’s maxi dress is the cutest thing I’ve ever seen. Available in a variety of different colors and sizes (from toddler to 10), it’s nice and versatile. It’s also comfy and lightweight enough for a warm day.

14

A Collared Dress

If this collared dress doesn’t scream “back-to-school,” then I honestly don’t know what does. Chic, studious, and sophisticated, this dress is beyond adorable. And it’s available in sizes from 3 months old to 12, so feel free to buy in a variety of sizes so it basically lasts forever.

15

An Elbow-Sleeved Dress

Not into strapless? This dress is perfect. The smocked top and slightly puffy sleeves give it a little bit of an edge, but it’s still simple and versatile. This works well on warm first days and will be able to be worn through the fall with a pair of tights.

16

A Skirt Dress

This toddler dress is the best layering dress. It’s basically a skirt with straps, and it goes really well over a tank top, short sleeve shirt, or long sleeve shirt, so it’s super versatile and can be worn in chillier weather as well. The oversized buttons are a stylish touch.

17

A Functional Dress

This active dress is basically like a skort in dress form. Underneath the wrap style skirt is a pair of shorts that makes this easy to run, jump, or just act like a kid in. The stretchy material is comfortable, and I love this dark floral that doesn’t feel too girly.

18

A Polo Dress

Trendy, simple, and a little bit preppy, this polo dress is both casual but also feels dressed up enough for a first day of school occasion. The navy blue makes it easy to wear and pair with other accessories.

19

A Party Vibe

For the girls who like to be as feminine as possible, there’s this adorable floral printed puff sleeve dress. Janie & Jack collaborated with Disney for an absolutely dreamy Alice In Wonderland collection (and it won’t last long!), and this one is just perfect for a party or for the first day of school.

20

A Printed Tunic

Colorful, bright, and fun, this tunic dress features huge red cherries on the front. I love how playful this one is, and it’s also versatile for a lot of different weather situations.

The big perk of all of these dresses (besides the fact that they’re adorable) is that most of them are super versatile: wear them on their own for warmer days in September, and as it gets cooler, get creative by layering them with other tops or tights. These are so great for a variety of occasions as well. Try not to buy them all!