15 First Day of School Outfit Ideas
- 1/15
Button-Down Shirt
Top any outfit with a preppy button-down shirt and you’ll ooze scholastic chic. Pair it with tailored pants for a sophisticated look or a skirt to keep it girly.
Personal style blogger Lorena paired her embroidered take on the oord shirt with super-bright shorts and oversized sunglasses for a look that’s smart and stylish.
- 2/15
Anorak
Slip on a thin windbreaker to beat the early-morning drizzles and add a chic twist to your outfit. Not only does it add an extra layer of warmth, but it also doubles the coolness of any dress.
Toughen up a lacy, feminine frock by tossing on a lightweight parka like blogger Gabrielle Lacasse. Her perfectly undone look is at once simple and stylish.
- 3/15
Camel Pants
Be ahead of the trend by reaching for camel colored-colored jeans instead of your trusty blue skinnies. Classic khaki looks chic with neutrals, but looks every bit as awesome with layers of bright colors.
Blogger Amanda Holstein stayed on the safe side with her softly-hued palette, wearing her pants with a cozy cream sweater. Her short moto-inspired boots add an extra edge to her outfit.
- 4/15
Maxi Skirt
There’s no doubt about it: maxi skirts are here to stay. Rock a floor-grazing number but keep it casual with a soft printed tee shirt.
A slightly sheer emerald green skirt like Natalie’s fulfills the glamour quotient. She accessorized with a giant studded carryall (perfect for textbooks!) and an edgy cropped ’do.
- 5/15
Bright Blazer
For a fun take on the classic blazer, choose a piece in a bold color. Toss a statement jacket over your go-to jeans, favorite shorts, or floral sundresses instantly spunky outfit.
Fashion blogger Aisa Ipac’s red blazer is on our wish list! She highlighted the color by wearing a rainbow-striped button-down shirt underneath.
- 6/15
Oord Shoes
For a fun take on the classic blazer, choose a piece in a bold color. Toss a statement jacket over your go-to jeans, favorite shorts, or floral sundresses instantly spunky outfit.
Fashion blogger Aisa Ipac’s red blazer is on our wish list! She highlighted the color by wearing a rainbow-striped button-down shirt underneath.
- 7/15
Layered Tops
Layering shirts is a surefire way to create a unique, quirky outfit. Try mixing patterns and textures to the best effect.
Blogger Annie Chang layered two lightweight button-downs over a classic gray tank, and added even more visual interest with a mix of necklaces, bracelets, and rings.
- 8/15
Double-Breasted Jacket
Inject a taste of menswear into your wardrobe by topping an outfit off with a simple double-breasted jacket, whether it’s a take on the blazer or trench.
Personal style blogger Willabelle Ong accented her striking primary color-hued outfit with a shrunken tan trench, pushing up the sleeves to expose the cuffs of her sheer shirt. She grounded the look with thick black leather booties.
- 9/15
Printed Pants
Take a wild walk in a pair of punky printed pants. Smarten up a soft jersey pair with a blazer, or go trendy with a vibrant top and statement belt.
We love how blogger Maddy accented the tribal print of her harem pants by wearing them with simple pieces in black, grey and orange. A carefully mussed topknot finished her downtown cool look.
- 10/15
Striped Shirt
This nautical-inspired top is a fashion-girl favorite, and for good reason. The classic boatneck striped shirt looks great worn with dark denim, frilly florals, and everything in between.
Adorable girl-next-door blogger Jennifer Hsieh paired her sailor tee with a sweet mini skirt and soft grey heels for a great school-approved outfit.
- 11/15
Knotted Shirt
Tie the tails of your favorite button-down for a quick way to show off a circle skirt. It’s a great way to give an oversized shirt a stylish shape.
Blogger Catherine E. chose a beige shirt with button detailing at the sleeves, accenting the neckline with a chunky silver necklace. She showed off her flirty peacock-feather printed skirt by knotting her workshirt at the waist.
- 12/15
Statement Belt
Buckle on a stylish waist-cinching statement belt this fall. It’ll work equally well over a dress as it will over a long top and jeans!
Hats off to blogger Priscila Betancort, who paired her peplum-skirted dress with a simple wide belt and nude flats.
- 13/15
Pleated Skirt
Pleated skirts aren’t just for elementary schoolgirls anymore; the style has matured to the fashion big-leagues. Play up the retro feel with ladylike accessories.
Personal style blogger Ivana Julian paired her blue skirt with a matching hair bow with white polka dots and structured purse, and played up the swishy skirt with strappy heels.
- 14/15
Light Sweater
Keep cozy in a light sweater—try a crochet knit for a look that’s both bold and breezy.
Personal-style blogger Megan Solla bookended her outfit with short black booties and a matching floppy hat. Her denim shorts and white sweater keep her look casual.
- 15/15
Workshirt
Top a girly or casual outfit with a denim workshirt for a cool way to dress it down. Try a faded tint for a vintage vibe.
The acid wash of blogger Aimee L.’s oversized workshirt complements the two shades of red in her outfit. Pushing up the sleeves gives her a more modern silhouette and edges up her look.















