Outfit #1: Polo shirt + jeans + corduroy jacket

If your child is in:

Preschool: Swap the polo for a T-shirt with her favorite cartoon character.
Grade-school: Kid-friendly corduroy in a neutral color instantly becomes a wardrobe staple.  
Middle School: It’s all about accessories. Add some bracelets or a necklace, or have her personalize the jacket with buttons on the collar or pockets.

Outfit #2: Dressy shirt + cardigan + cargo pants

If your child is in:

Preschool: The eyelet collar is great for dressier occasions, but still comfy enough for everyday.
Grade-school: A long cardigan can pull double-duty as a dress.
Middle School: Even growing tomboys will love the girly touch of sequins on these cool cargos.

Outfit #3: ¾ sleeve dress + printed long-sleeve shirt + footless leggings

If your child is in:

Preschool: Keep dresses playground-ready by choosing loose, machine-washable fabrics and shapes.
Grade-school: Stay fashionable with footless leggings. Look for neutral shades like black and brown to wear under skirts, shorts and long tunics.
Middle School: Choose contrasting prints in coordinating colors to look effortlessly stylish.

Outfit #4: Corduroy jacket + printed long-sleeve shirt + colored jeans

If your child is in:

Preschool: Jeans in different shades give outfits a cheery pop of color.  
Grade-school: Get extra mileage out of lightweight jackets by using them as blazers in the winter.
Middle School: Add some layering to this outfit for a grown-up touch by throwing a collared shirt underneath the printed top.

Outfit #5: Long cardigan + polo shirt + footless leggings

If your child is in:

Preschool: A long cardigan is a good alternative to a jacket.
Grade-school: When shades of pink won’t do, mint green and sky blue still look feminine paired with neutral basics.
Middle School: Adding a cap or headband is a great way to up the fashion ante for this look.

Images Courtesy of:

• Old Navy
• Macy’s
• EarthChild
• Disney SHopping
• Wal-Mart
• H&M