10 Cute Outfits for School

kids with cute outfits

Our clothing choices are our individual artistic endeavors. What we wear turn us into a masterpiece of our own tastes. Unlike many works of art, clothes don’t hang on the walls of an art museum, staying pristine and untouched. We use our clothes! Whether you are age 5 or age 55, choosing the right outfits to show off your glam and your quirks while staying clean and comfortable enough for studying, sitting in class, and playing can be challenging. The challenge only increases if you’re shopping for your kids! Balance form and function in any wardrobe with these 10 cute outfits for school that work for all ages and genders.

Back to School

Back to school shopping is awesome! We pick out tons of cute jackets, trendy jeans, and on-point boots. Kids go to school looking like the future CEOs of the U.S., and we go to classes feeling like kings and queens in our new threads. Everyone we meet sees us in the things we wear. Our clothes communicate who we are more than any other pieces of visual art, and we get to wear them all day long.

About a quarter of the way into the school year, though, we notice that it’s getting colder outside and our trendy t-shirt isn’t quite enough to block the chilly wind, and our leggings are feeling just a bit too tight for us to pay attention in math class. Then our favorite sweater gets a hole where the loose thread used to be. One of the biggest challenges we face with wearing our cute outfits for school is keeping them that way.

The New Look

Elegant and Sassy

man in shades

It seems like the modern look is both elegant and sassy. Thankfully, previous generations ironed out the details of a long-lasting, effortlessly elegant look. We now get to add some sassy flair to our looks to keep them in the 21st century. Some of the most popular ways to spice up a look are denims, floral patterns, retro pieces, inspirational quote prints, and athletic pieces.

Remember Your Bag

bag and book

When you build your cute outfits for school, think about how long you will have each piece and what pieces you will wear most often – this includes accessories! A great way to get started is to find your most-used accessory and build on it. If you use the same backpack or purse all year, find colors, patterns, and styles in your outfits that compliment your bag.

The Outdoors Still Exists

Donning some well-placed layers is another way to keep your look trendy and functional all school year. Winter can be abrasive and chilly outside, but most schools overcompensate with heat in the classrooms. Make sure you beat the weather versatile layered outfits that can change with the seasons… and with the indoor temperatures!

Is That Tailor Made?

tape measure

Notice the material and cut of each item you choose. Do jackets and shirts stay on your shoulders, not too tight or too loose around your arms? Do pants, jumpers, dresses, or skirts feel comfortable when you’re sitting, walking up stairs, outside in the wind, and standing in a hallway? If you treat your bedroom floor like a closet, maybe look at materials that are wrinkle-resistant.  You don’t need tailored suits every day to look and feel great. If you pick the clothes that fit just right and stay fresh, your cute outfits for school will turn heads for weeks and stay comfortable.

The Three Shoe Rule

Finally, to keep each look as functional as possible, plan ensembles you can wear in tons of different ways to capture the intended visual effect modified for different occasions. These outfits make great use of jackets, leggings, sleeves that roll-up, and shoes. Ideally, every outfit can be worn with three alternative pairs of shoes that each say a little something different about the look. If you can only wear an outfit one way, you won’t find it in this list of cute outfits for school.

10 Cute Outfits for School

Whether you are back to school shopping for your kids or digging through your closet for some inspirational collegiate wear, you should easily be able to pull together these 10 cute outfits for school!


floral dress

Floral print is a staple. It is incredibly easy to take care of a basic floral dress or button-down on a wrinkle-free fabric. There are all kinds of floral prints, and most hide stains like someone designed them to soak up last night’s spaghetti. If you grab a floral pattern that accents mauve, navy, or olive green, it can work for every season!

A Floral Dress Works With

  • A 3/4 sleeves or if it has sleeves that can be rolled up
  • Denim jacket in some weather
  • Leggings (pick a color from the floral for extra pop)
  • Sandals (with or without heel)
  • Booties + boot socks
  • Slip-on sneakers

A Floral Shirt Works With

  • Rollable sleeves
  • Pair with light color jeans/slacks to give the floral room to play
  • Denim jacket (avoid clashing with the jeans)
  • Slip-on sneakers
  • Casual dress shoes (better if laced)
  • Combat or hiking style boots

Classic Dark Jeans

Dark Jeans

Dark colored jeans and even black jeans take a fairly relaxed look to the next level. Almost any tee or blouse will work with dark jeans, but we love the elegance of a solid, lighter or warmer color shirt on top. This look can bring back the classic “white-tee” look in an instant, or even transition you from class to a night out with a cute blouse or button-down. Dark jeans are a great understated base for shirts with empowering and sassy statements in loud and proud fonts.

Dark Jeans Work With

  • A skinny ankle for shoe versatility
  • A rolled-up ankle on warmer days
  • White, gray, cream, and other light color shirts
  • Some lighter pinks, purples, and warm color shirts
  • Bold and encouraging statements (watch the font)
  • Loose-fitting shirts for a more boho look
  • Closer-fitting shirts for a more crisp look
  • A good bomber jacket
  • Slip-on sneakers
  • Flats that coordinate with the shirt
  • Square-heeled boots or knee boots

Casual Light Jeans

Light Jeans

Wearing light-colored jeans is similar to using the dark jean look; almost any color shirt will work. The biggest difference is that dark jeans take most looks up a notch while lighter jeans keep it chill. Light jeans have a way of making the wearer look relaxed and approachable. They are also a great base for bringing out crazier patterns and darker colors shirts.

Light Jeans Work With

  • A skinny ankle
  • Grays, greens, blues, and dark color shirts
  • Crazier prints on top
  • Lighter color shirts for a super casual look
  • A large, knit pullover sweater for chilly days
  • A long, loose sweater with pockets (gray works for almost every look)
  • Sandals
  • Slip-on sneakers
  • Brown/tan flats or boat shoes

Sweatshirt Accent


On the days when you roll out of bed and have a class in 10 minutes, a sweatshirt makes a cute outfit for school accessible! You can wear a big, loose sweatshirt with leggings to get the sporty feel or a knit sweatshirt with skinny jeans for a classic boho look. In warmer weather, a cropped sweatshirt with the ankle of your pants rolled-up keeps you cool. If you’re not a fan of the athletic look or the feel of sweatshirts, you can apply this same look to an oversized or cropped sweater.

A Sweatshirt/Sweater Works With

  • Skinny Jeans, Leggings, or shorts
  • Slip-on sneakers
  • Combat boots
  • Activewear sandals

Joggers Accent


Joggers, even super posh pleated joggers that look like slacks, are your friend when you want something that looks different and still feels comfy. The slightly high ankle on joggers makes room for trendy shoes, and the loose, wider leg at the top contrasts nicely with a close-fitting tee. This look feels sporty, too, but can be amped up to chic with the right black joggers and heels.

Joggers Work With

  • Short- waisted, tighter fitting tees
  • A cute, short sweater for chilly days
  • Slip-on sneakers
  • Thicker heels
  • Some combat boots

Presentation-Day Chic

Chic dress

The key to this look is to keep it simple and make use of black and white. We suggest finding a shirt or dress with a fun, geometric black-and-white pattern. Everything about this look shows clean lines. You will be ready for your presentation day and the other seven hours of class lectures in this cute outfit for school.

A Black-and-White Dress Works With

  • Leggings (or stockings if they are mandatory) for chilly days
  • A simple 50s-throwback black sweater
  • Black booties
  • Black heels
  • Black sandals

A Black-and-White Shirt Works With

  • Black skinny-leg slacks or a pencil skirt
  • A simple black sweater or blazer
  • Black heels
  • Some white heels
  • Black sandals
  • Black dress shoes for men

Turtleneck Comeback


90s era and other retro styles are back in, and we are honestly wondering if a little well-placed retro ever left. Turtlenecks are a great example of a simple, but classy retro piece used to build a great outfit. To avoid getting overheated, try a lightweight, sleeveless turtleneck. You can always pair it with a sweater for a great winter look!

Turtlenecks Work With

  • Sweaters of similar length to the turtleneck
  • No sleeves
  • Skinny jeans, skinny slacks, or leggings
  • Sandals
  • Booties
  • Flats
  • Knee boots
  • Slip-on sneakers
  • Some heels

Overalls and Jumpers


Overalls and Jumpers are a diverse category of apparel, but both help you stand out in a crowd. For a more dressy feel, try a good jumper – maybe in floral! For a casual and classic look, go with lighter -color overalls and a cute tee. If you tire of the look, cut off the legs for the overall shorts look.

Overalls Work With

  • A cute tee
  • A skinny-leg or jogger-esque cut
  • Long, loose sweaters
  • Slip-on sneakers
  • Combat Boots
  • Booties

Bold Patterns in Bright Colors


If you are accident prone, bold patterns are your friend. The closer-together the pattern, the more you can hide virtually any spill or pencil mark. If you have an 8 am art class, this look is for you.

Bold Patterns Work With

  • Some other bold patterns (shirts and pants or shirts and sweaters)
  • Bright colors
  • Skinny jeans
  • A sharp-angled jacket or blazer
  • Most shoes (determined by color and pants cut)

Going to Grandma’s House After School

little black dress

This look may sound like a bland staple, but it is an in-school equivalent to the “little black dress” and works for almost any occasion. Simply wear a pale blue button-down, dark jeans, and lighter-colored shoes. Grab a lighter-colored sweater on chilly days.

This Look Works With

  • 3/4 sleeves or sleeves that can be rolled
  • A solid color, light blue button-down with a collar
  • A white undershirt
  • Darker blue denim skinny jeans (ankle can be rolled on warm days)
  • A light-color waist-length sweater (white, cream, tan, light brown)
  • Light-color shoes (sneakers, boat shoes, sandals, flats, booties)


Keep your look in style with cute outfits for school that are both functional and fashionable.

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