Ten Must Have Fall Outfits for Boys | Lands' End

Ten Must-Have Fall Outfits for Boys

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 boy's winter coats options that he will need before long too.

1. The first day of school

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.

2. The hayrider

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.

3. The leaf peeper

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.

4. The leaf jumper

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 sweatshirt or a fleece jacket.

5. The sledder

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).

6. The puddle splasher

Whether it’s heavy rain or snow melting after the sun comes out, you can count on standing water. You can also bet your bottom dollar that he is anxious to jump in at least one of those puddles. A pair of rain boots to wear on his walk from school should let him be the king of splashing. Paired with a down waterproof winter parka and getting wet will be the last of your worries. Keep his feet warm with a thick pair of socks and have a nice warm cup of hot chocolate waiting for him as his after-school snack along with a towel to minimize the wet mess he’ll be tracking with him. 

7. The pumpkin picker

October is the perfect month for fall weather activities such as the pumpkin patch. It’s not quite freezing but it’s also not the warmest, especially if you’re outdoors in the evening in search of the perfect pumpkin to bring home with you. Because there are usually other activities to enjoy such as a corn maze, a petting zoo, rides, and watching competitions, a pair of tech fleece joggers with a hooded sweatshirt over a t-shirt is all he needs if the day is on the warmer side. If you feel like he could use an extra layer, add a denim jacket on top of the hooded sweatshirt. Be sure to bring shoes that can get dusty since he’ll be walking on dirt the entire time.

8. The Thanksgiving fashionista

Thanksgiving is one of those holidays where you have to dress up to sit at the table with relatives while you eat until you’ve reached a food coma. While looking your best is the goal here, being comfortable should be at the top of your list. There’s nothing worse than being uncomfortable, trying to loosen up a belt after a serving. Give him the best of both worlds by putting together a fashionable outfit that he will enjoy wearing. A pair of stretch pocket cotton pants with a dress shirt and a pullover cardigan is so GQ along with a pair of Chelsea boots or low-top sneakers. It allows him to take off a layer if he’s too hot while the pants don’t jab his waist as he sits to enjoy a second serving of his grandmother's favorite pie.

9. The turkey bowl player

Who doesn’t enjoy a game of flag football especially when the star player is your kid? It may be cold outside but with all of that running, he’ll be breaking a sweat so it’s best to keep him just warm enough. A pair of fleece jogger pants, a long sleeve shirt, a hooded sweatshirt, and a fleece hat or face mask are all he’ll need to keep him warm and comfortable. Bring an extra jacket and some gloves in case the weather decides to act funny because fall weather can be unpredictable.

10. The Christmas card  

Christmas card photos are usually taken right before Thanksgiving to allow the photographer ample time to edit and the printers to print and ship. Family Christmas cards range from matching pajamas to formalwear and everything in between. If this is your chance at a formal family portrait, you can’t go wrong with a black suit jacket, a white dress shirt, black dress pants, and a pair of clean white sneakers. Polish off the look with a bowtie in a festive color or have the bowtie match the color of the mom’s dress for a more coordinated look.


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