When it comes to fall there are two absolute certainties: the leaves will drop from the trees, and boys will require a few new outfits. Occasions like the first day of school will need him looking his very best, while outdoor activities like leaf peeping and the annual hayride call for utilitarian clothing that can keep up with his play. And because you can't count out a November snowstorm, we'll be sure to cover the boys winter coatsoptions that he won't need before long too.
When it comes to making a first impression, the first day of a new school year is a tough occasion to beat. You can even think of it as the kid-version of a job interview. Naturally, you'll want him looking his very best in front of his new teacher and classmates. For a clean and classic look, think of starting with a pair of crisp chinos. To avoid being too dressy, combine it with a casual polo shirt. The other items are a little more functional: a backpack for those new books, and a new hoodie to stay warm during those chilly mornings waiting for the bus.
What could fall be without a proper hayride? For this classic fall outing, you won't have to worry about making an impression: your main concern will be what kind of clothes can make it through a corn maze and back unscathed. For that reason, consider a classic pair of jeans paired with a rugby shirt. If things get a little bit chilly at night, bring along a sweatshirt or a fleece jacket as a second layer. And if there's any chance of apple picking, be sure to have a sports bag in tow.
The annual shift from green leaves to shades of yellow, orange, brown, and many, many more is as good a reason as any to load up the car, take a trip north and embark on a hike to see those changing colors up close. Start his leaf-peeping outfit with a pair of cargo pants that can accommodate a granola bar or a pack of trail mix. Keep it casual up top with a boy's polo shirt or a rugby shirt, but bring along a fleece jacket if you think your foliage tour may last past sundown.
There's no way to avoid it: no matter how many careful piles of leaves you rake up from the lawn, at least one of them is going to be jumped in. Embrace the ritual, and provide him with an outfit suited to this cardio-intense activity. A pair of stretch jeans will move with him from pile to pile, and a rugby shirt is knitted tough enough to take the fall. If you think he might need another layer for warmth—or to cushion his fall—consider including a sweat shirt or a fleece jacket.
The tail of fall brings the first snows of winter, and with it, the first real chance to make a snow angel, build a snowman, and of course, sled. Needless to say, the top priority for any outfit worn in a winter wonderland is going to be warmth. Build the base layer with casual, comfortable clothing that can provide warmth while being layered over, such as a pair of stretch jeans and a sweatshirt. Afterward, combine these with snow pants and a winter coat or a winter parka. It goes without saying that you'll want a pair of snow boots that can warm feet and provide traction in case the going gets icy (always a probability).