Outfit #1: Striped polo + hooded jacket + jeans

If your child is in:

Preschool: Swap a basic denim jacket for a durable cotton/twill version for versatility.
Grade-school: Whether for school or weekend attire, polo shirts meet the dress code for any occasion.
Middle School: Jeans are musts for any boy, but skip lighter washes in this age group – darker versions tend to work well with almost any shirt or jacket.

Outfit #2: Button-up shirt + turtleneck + cargo pants

If your child is in:

Preschool: Load up on patterned shirts if stains and spills are an everyday occurrence. They’re stylish and hide marks better than any plain shirt can.
Grade-school: Buying basics in different colors is a great way to save. Here, grey is a fresh alternative to khaki cargo pants.
Middle School: Make wardrobe pieces pull double-duty. This button-up shirt would also hold its own when paired with dress pants.

Outfit #3: White long-sleeve shirt + dress pants + jacket

If your child is in:

Preschool: Keep him comfy (and still stylish) by tucking in his shirt, adding a belt, and throwing on a pair of cool sneakers.
Grade-school: Long-sleeve shirts are a great layering piece under everything from sweaters to team sport jerseys.
Middle School: Dress things up by adding a blazer or knitted vest to this outfit.

Outfit #4: T-shirt + turtleneck + cargo pants

If your child is in:

Preschool: Boys love action figures, so choose a shirt or pair of pants adorned with their favorite movie or television character for a bit of fun.
Grade-school: Even if he likes the rest of his clothes baggy, choose proper fitting layering pieces and he’ll never look sloppy.
Middle School: Make the look more casual by swapping the turtleneck for a T-shirt.

Outfit #5: White long-sleeve shirt + camouflage-print hoodie + jeans

If your child is in:

Preschool: Forgo tricky zippers when dealing with little fingers. Fuss-free pullovers work perfectly for this time of year and allow your little one to get dressed without any help from mom.
Grade-school: Dress up this outfit by swapping the hoodie for a v-neck sweater, and add dress shoes for a quick change of style.
Middle School: A studded belt or high-top sneakers would complete the look and give it a rock star twist.

Images Courtesy of:

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