Easy on, easy off
With cooler weather arriving, your kids will need both inside and outside clothes. If you have younger kids, make sure they can do up their jacket buttons themselves, and remember that loose-fitting clothing in general is easier to put on. Cathy Dunne, a seventh-grade teacher in the Toronto area, explains, "To avoid teachers having to help a whole classroom put on and off their outdoor clothes several times a day, we encourage kids to wear clothes that they can put on and take off by themselves. That goes for trips to the bathroom too—younger children should be able to take down and do up their own pants."

The shoe fits
Your child will probably need two pairs of shoes—one indoor and one outdoor. Some teachers don’t allow outdoor shoes to be worn in the classroom, so your kids might need to change throughout the day. Again, keep it simple. "Don’t send young kids to school with lace-up shoes if they can’t tie them," Dunne says. "Buy them Velcro shoes instead."

For gym class your child will need shoes with non-marking soles. And, in addition to a good pair of running shoes for the playground, older children who play sports should have proper footwear designed for the sport the play. High-top basketball shoes, for example, provide the ankle support your child needs on the court, and cleats provide the traction necessary for baseball and soccer.

When buying footwear for your kids, avoid ill-fitting shoes that are too big—these are rarely comfortable. Instead, the general guideline is that there should be a thumb’s width between the end of their big toe and the end of the shoe. To ensure the best fit, buy shoes in the afternoon or evening when the feet have swollen.

Trendy but simple
You can never go wrong with a classic T. This year vintage-inspired T-shirts are all the rage, according to Annie Helegda, trend manager for Sears Apparel and Accessories. "T-shirts are great layering pieces and a great way for kids to express their individuality," she says. "Messages on T-shirts this year are upbeat and fun and sports logos are still popular." For boys, stylish plaid shirts are also popular thanks to their versatility. They can be worn buttoned-up or buttoned-down with a T-shirt underneath. Track jackets and hoodies work well for cooler weather.

For pants, stick to durable denim. Helegda recommends loose-fit jeans in vintage or distressed washes as the hot style for boys. Jeans with embroidery and topstitching are all the rage for girls.

Be sure not to skimp when it comes to footwear. Kids’ shoes need to be durable, comfortable and something they’ll want to wear every day. Athletic sneakers are popular and a good fit this year for both girls and boys. Colorful ballerina-style slip-ons are also popular with girls.

What the kids say

And now it’s time for the real experts. We asked the Zeeks kids, aged nine to 14, what styles they think are cool for school. Here’s what they said:

I’m going to school in jeans and a blouse with my favorite flip-flops! -kit_kat

This is my last year before high school so I’m going to school looking cool with designer jeans, tank tops and other tops that look just plain cool! I’ll also have the newest shoes and the flyest hair-dos! -songo13

All you guys in America are so lucky! In England we get stuck with uniforms, so we can't wear what we want. -emo_kid