How to Dress Boys Nicely

Dress 'im to impress 'em.

Congratulations, it's a boy! But unless the hospital gave you more than that fuzzy blue blanket, you'll probably need to start buying clothes. There are lots of choices when the little one starts growing up and whether it's summer or winter, or a day at school or temple for a wedding, helping your boys dress can get a little tricky. Here are some styles to think about.

Things You'll Need

• Jeans
• Polos
• Collared sport shirts
• Stylish tees
• Blazer
• Dark jacket
• Suit
• Shoes

Instructions

1. Keep an eye on comfort. This doesn't refer just to clothes — your son or nephew needs to be comfortable in what he is wearing. If not, expect lots of whining and extra stress at school. Still, it's your role as mom or dad or cool uncle to push them just a little bit in the right direction, away from sagging jeans and stained T-shirts, toward suit jackets that fit and dinner attire that doesn't make the maitre d' run screaming from the restaurant. Of course, do find threads that are comfy to wear.

2. Get expressive with active, energetic clothing. Casual clothes should let him show people what he likes. Graphic Tees with his favorite bands are cool, or skateboard and surf shirts might give him a little edge with the little ladies. These can look nice with a little effort: a stylish t-shirt under a blazer is a popular look for everyone, from boys to young adults to movie stars.

3. Dress him up. Flannel and collared sports shirts are great for all ages, or get him a couple polos like Dad. (Popular men's styles can just as well be classy boys' styles — but be careful. Mini-bow ties and pint-sized fedoras are forcing it.) If he gets used to modern, mature trends at a young age, he will develop a strong sense of style. That said, don't get him "Project Runway" DVDs for Christmas.
   It is also important to have a suit in the wardrobe. Dark suits, black or navy, are flexible for many well-dressed occasions.

4. Find him denim that works. Every wardrobe needs some jeans, perfect almost all year around and extremely versatile between outfits. Some styles are louder and covered in embroidered patterns while others are more stylish. Let him choose, but remember, you've got a veto.

5. Layer, layer, layer. Over the T-shirt, throw a collared flannel — over that you've got a zip-up hoodie under his favorite jacket. Layers physically feel secure and let kids (and the rest of us) feel like we're making bold stylistic choices. When it's cold out, pick out thin sweaters to put under blazers or a thicker, dark jacket that looks good over anything. Remember: don't make the choice for him — find different styles and let him pick, and don't let him wear the same thing every day.

6. Get some fly kicks — casual shoes can go with dressed-up looks, but not the other way around. Shoes are super important for any boy to feel like his outfit's complete. Comfy skate shoes are easy, or go for more colorful running shoes, or modish new styles. Shoe stores can be like candy stores for kids: Go to a couple places (or one) and look around — see what he likes and ask the salespeople for help.

7. Top it off with a hat. Beanies are great for the winter, and they make it so that he doesn't have to touch his hair in the morning. Baseball caps are great conversation starters and accent many casual looks. Find the right lid (if he's into hats) and he'll be looking cool top to bottom. Remember: Casual accessories like these work well in combination with something more formal — dont send him off in a beanie in sweatpants, but top off a jacket-collared shirt combo with a cap and he'll look put together.

References

• Esquire: How to Dress Your Son