First Day of School Outfits

Crystal Schwanke
Back to school

When the first day of school is just around the corner, it's time to start shopping for clothes that fall into the happy medium area between dress codes, the newest trends, and your family's budget. Clothes that are comfortable, on trend, and versatile are the way to go.

Elementary School Girls

Stock up on cute shorts, tights, or leggings to go with a collection of dresses (and skirts) for modesty on the playground. You can usually find inexpensive cotton shorts that feel comfortable and go unnoticed under a dress at stores like Old Navy (less than $10.00).

Girl wearing purple striped tights

Dress Options

A cute, mid-length dress like the Cap Sleeve Skater Dress (around $10.00 at JCPenney) is always another winning option for elementary school girls. The Floral Keyhole Tiered Dress from Justice (under $30.00) is another cute option and has 3/4 length sleeves.

Leggings Sets

Pair up a top and leggings with or without a vest or scarf. You can even find whole outfits sold together in department stores that will take the guesswork out of shopping for you.

For a top and bottom combination, try the 4-piece Cozy Leggings Set from JCPenney (around $50.00). You might also consider pairing leggings from Justice (around $15.00 to $20.00) with a coordinating tunic or T-shirt. Finish the outfit with short boots, sandals, or sneakers, depending on the dress code.

striped tunic with sneakers

Elementary School Boys

Plaid or brightly colored shorts and a t-shirt are a quick and easy outfit solution for boys. Plaid is huge for fall, and this is one way to bridge the gap between long, hot summer days and the welcoming in of a new school year, while bright colors are still fun when it's hot out. A t-shirt with a favorite character on it in a complementary shade (or just white) will keep him comfortable and cool all day.

plaid shorts with matching tee
Plaid shorts with matching tee

Pair Bottoms With Graphic or Colorful Tops

Try some Flat-Front Shorts (less than $20.00) and a t-shirt like the Teenage Mutant Ninja Turtles Face Graphic Tee (under $10.00 at Target). You could also go the cool, comfortable, and classic route by pairing up a t-shirt with some blue jeans and sneakers. You can't go wrong with that! Try the Volcom Straight Leg Kids Jeans from Nordstrom with a graphic tee.

Cargos With Button-Ups

The combination of neutral-toned cargo shorts or jeans and a button-up (or t-shirt) can incorporate that plaid trend if you'd like, but it doesn't have to. Once you have the shorts or jeans picked out, find a button-up with short sleeves in his favorite colors. You can either have him wear it buttoned down the front or open with a t-shirt underneath.

Try out the Boys' Levi's Belted Cargo Shorts (around $30.00, Kohl's) in their Monumental Plaid color option, or go for a solid light or dark khaki shade. For the plaid shirt option, there's theJ.Crew Boys' Short Sleeve Slim Washed Shirt (less than $30.00), available in aqua tile or rose tile. If you want to go the t-shirt route with or without the plaid, what kid wouldn't like a shirt with patterned sharks (GAP, less than $20.00)?

Boy in plaid shirt and shorts
Cargo shorts with plaid button-up

Middle School Girls

Your girl may have already been a little fashionista in elementary school, but these are the days she'll probably really start paying attention to fashion and considering what her friends are wearing, as well as what everyone thinks of what she's wearing.

Slim Jeans With Plaid Shirt

Help your daughter navigate the dress code and social expectations with shorts, skinny/slim jeans, or an A-line skirt, paired up with a fitted tee/cami, plaid flannel, and sandals or low-top sneakers.

Take a look at the Sparkle Shoulder Glitter Plaid Shirt (Justice, around $25.00), available in four color choices. Paired up with some jeggings like the Knit Waist Jean Leggings (also from Justice and around $20.00) and Lacey Cami (Justice, under $10.00), this will make for a winning, casual combo you can pick up at one store for right around $50.00.

Girl in skinny jeans with plaid top
Skinny jeans with plaid top

Loose T-Shirt With Jacket and Jeans

Another option is a pair of skinny jeans, loose-fitting ultra-soft t-shirt, wedge booties, and a cute hair accessory. Optional: a tunic-length cardigan or light jacket in her favorite color, in case the classrooms are chilly.

Zip Hoodie Frank & Eileen Tee Lab
Zip Hoodie

Middle School Boys

Classic combos get an update as boys transition from elementary to middle school.

Shorts With Button-Ups

Cargo shorts, jean shorts, or joggers (like the Levi's Boys Ripstop Camo Jogger Pants, under $50.00 at Macy's) and a t-shirt will work great for middle school boys, with an optional short-sleeved button-up on top. Sneakers or sandals pair perfectly with either option.

A Volcom Stone Fleece Hoodie and a pair of DL 1961 Jogger Pants (each piece under $40.00) will look great in cooler months.

boy in plaid shirt and shorts
Shorts with button-up

Preppy Polo Look

Jeans and a polo (check out the Ralph Lauren Pique Polo, less than $30.00) or raglan t-shirt (take a look at the Urban Pipeline Raglan T-shirt, less than $10.00 at Kohl's) will also work.

Have him pick his favorite style of jeans. Some boys like wearing the more relaxed, straight-leg style with a polo, while others like the more fitted jeans with t-shirts. A pair of Vans (or similar shoes) will work with either jeans combo.

Young teenage boy jeans and polo
Polo with jeans

High School Girls

Look for casual chic style. Skinny jeans or leggings, flowy hi-low tops or flannel (maybe even with crocheted back detail), and low-top sneakers, sandals, combat boots, or booties (lace-up boots even work with the leggings!) work well for the first day back. Skinny jeans, a more fitted t-shirt, and a lightweight infinity scarf will also look nice and should also adhere to the dress code.

Skinny Jeans With Plaid

The So Button Down Plaid Shirt (under $15, Kohl's) could be paired with the Forever 21 High-Rise Skinny Jeans (less than $30.00) and any basic tee.

High school girl wearing black plaid shirt
Skinny jeans and plaid shirt

Chambray Style

A chambray button-up (like Forever 21's version, available for around $20.00) paired with white shorts or jeans (like H&M's Skinny Ankle Jeans option for under $20.00) will be the perfect crossover combination between summer and fall. For shoes, wedge or flat booties in tan or black will work with jeans, while leather (or faux leather) sandals will go with the shorts.

Mismatched denim is another take on this look. Try a lighter tone on top and a dark wash on the bottom. For example, you could pair the Levi's Vintage Denim Shirt (around $40.00 at Macy's) with the dark denim blue slim-fit pants from H&M (about $20.00).

Chambray shirt with mismatched denim
Chambray shirt with denim

High School Boys

High school boys often look for comfortable styles.

Stylish Polo Outfit

Straight leg blue jeans (like American Eagle's Extreme Flex Slim Straight Jean, around $50.00) or tan shorts (try PacSun's RVCA Week-End Shorts, under $50.00) paired with a polo is an option that never goes out of style. It's a safe bet that is more dressed up than your standard tee and jogger pants combo. Doc Martens or sneakers work well with these items.

teen in tan shorts and blue shirt
Polo with tan shorts

Hoodie With Jeans

A light hoodie is optional, depending on where you live, the start date for the schools in your area, and whether the classrooms are typically kept cold. The ASOS Oversized Hoodie (just over $30.00) is a good option.

Blue jeans (especially with a taper toward the ankle, like the PacSun Stacked Skinny Active Stretch Moto Destroy Dark Jeans (around $65.00), graphic t-shirt (around $25.00 from Hot Topic), optional plaid button-up (also Hot Topic, around $40.00), and sneakers (Converse or Vans) give off the cool guy vibe. Another pants option with a similar cut is the jogger, like the AEO Extreme Flex Jogger (under $50.00). Pair them up with a t-shirt or polo, low-top sneakers or high-tops.

Teen wearing hoodie with jeans
Hoodie with jeans

Shopping for School Clothes

When it's time to shop for those first day of school outfits (and more), things can get a bit stressful. Try to take some pressure off by shopping around online and looking for coupon codes to stack with sales. Venture out to the stores and brave the crowds only for a few things, if you have to (unless you love the thrill of that type of shopping experience, of course). Back to school shopping isn't for the faint-hearted, but if you're armed with a list of styles to try and a list of stores to visit, it can be easier than ever.

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First Day of School Outfits