How to Prep Your Son to Dress by Himself with The Belts, Boxers, T-Shirts and More

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As the boys become more independent and their styles become more individualized, you may find that your son will want to start dressing himself on his own. As a parent, there are a few key elements of their wardrobe that you can provide to make dressing himself much easier.

Here are the top four articles of clothing to make available to assist your son as he gets dressed.

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1. Tops

To make things easier for both sides of the equation, have a number of t-shirts available for your son. Having a drawer full of shirts at eye level allows your child to find a shirt they like, with minimal messes. Or, hang up their graphic tees in the closet to make for a more visually appealing way to find their tops each morning.

2. Underwear

Another essential in making for complete outfits for your son are their undergarments. Whether they wear traditional underwear, boxer briefs or boy’s boxers, it’s important to have these items in close proximity of the rest of their garments. It may seem like a given, but get your child in a rhythm of picking out a new pair of underwear and T-shirt everyday.

3. Bottoms

Teaching your son how to pick the appropriate bottoms is also important. Show them when they would wear workout shorts, pajama bottoms, jeans and fancier pants—along with which event is appropriate for each outfit. For example, you’d never want your child to wear his Sunday best when he’s going outside to play with his friends or going to the park.

4. Belts

One of the most overlooked items in a boy’s closet is his belts. While he may be under the assumption that he should only wear belts for fancy occasions, incorporating a variety of different boy’s belts into daily outfits keeps from sagginess in their pants and provides for a more complete look. Depending on their age, look for fabric or canvas belts that can be easily worn and can withstand daily use. For more formal events, look for brown and black leather belts that will match their dress pants and shoes.

Above all, find articles of clothing that they’re comfortable in. If you have a few sets of articles that they enjoy wearing, they’ll be more inclined to want to dress themselves with minimal assistance. Vineyard Vines clothing, for example, and other online stores are great resources for standard tops and bottoms, along with comfy tees, shorts and more.

Laura enjoys writing about many things. One of her favourites happens to be clothing. If you’d like to learn more about Vineyard Vines Clothing, please visit

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