Types of Preppy Boys Clothes

Boy looking preppy with bow tie

When it comes to clothing, the term "preppy" refers to a person who favors a particular style associated with traditional preparatory schools. A classic American aesthetic, preppy boys' clothes can make any boy look like a little gentleman, whether he's headed to a casual event or somewhere dressier.

Preppy Boy Key Pieces

Your son or daughter doesn't have to attend an exclusive prep school to wear preppy clothing. All your little boy needs are a few key pieces in his closet that define preppy attire.

The Oxford Shirt

A white, button-up Oxford is classic and timeless, but you can find striped versions in stores as well. While this type of shirt isn't practical for everyday play, it's perfect for other occasions such as weddings, religious services, and parties. Simply throw on a tailored blazer over the top of an Oxford shirt and madras shorts to epitomize smart casual cool.

schoolboy wearing oxford shirt

The Tailored Blazer

The tailored blazer is a great layering tool if you're looking to develop an undeniably preppy appearance. It instantly dresses up a casual outfit and gives it a contemporary update. When it's cold weather, get your little boy to wear an Oxford or polo shirt underneath some form of knitwear and then add the blazer for a fashion-forward, high impact result.

schoolboy wearing blazer

Neutral Chinos

Made of cotton, cotton-twill, or polyester, these casual pants are ideal for events that call for more than jeans. Alternatively, if it's warm weather, you can opt for their shorter counterparts. Either way, make sure that you choose chinos in a neutral hue like beige, tan, or khaki for versatility so that you can pair them with different colored tops and jackets.

schoolboy wearing chinos pants

Solid Knitwear

Knitwear makes a great addition to your little boy's closet as you can layer it for the fall and winter months. V-neck sweaters or button-up cardigans are considered particularly preppy, especially when teamed with an Oxford shirt and chinos. Whether your boy chooses to wear his knitwear or drape it casually over his shoulders, you can rest assured he'll be making the ultimate style statement.

schoolboy wearing knit sweater

The Polo Shirt

Available in a wide range of colors (including solids and striped), polos work excellently with shorts and slacks. Consider brighter, vibrant hues during spring and summer and darker, more understated tones for fall and winter. Add an argyle sweater vest to produce a cute, quirky ensemble.

schoolboy wearing knit sweater

Madras Shorts

These standout plaid print shorts work well with plain polo shirts during the summer months. Ideal for more casual occasions, you can invest in an array of colors and styles of prints that will suit your son's complexion and personal style. Merely throw on a sweater or cardigan over the top of his polo shirt in cooler weather to enhance his comfort level.

schoolboy wearing madras shorts

Argyle Sweater Vests

Argyle patterns come in a range of colors and can adorn an outfit in the form of knitwear or socks. However, it's the argyle sweater vest that's considered a preppy staple. Combine it with chinos and a polo shirt for a youthful-looking, cute appearance.

schoolboy wearing sweater vest

Preppy Boy Footwear and Accessories

Preppy clothes work for all ages, from young kids to adults. Even boys who prefer rough-and-tumble wear like tees and jeans can get dressed in preppy boys' clothes from time to time. If you want to dress up the aesthetic even further, consider a smart shoe or accessory.


Loafers are the perfect boy's shoe to team with chinos for summertime. When it comes to the fall and winter months, opt for lace-up brogues with funky patterned socks to match an argyle sweater vest or contrast a solid knitwear piece. This will develop visual intrigue.


Leather belts are a great way to smarten a preppy boy outfit. You can also add a tie with an Oxford shirt and tailored blazer for a more formal look. If you want to insert more personality into your son's outfit, consider a bow tie in a kitsch print or multiple colors. You can even get your little boy to wear eyeglasses as the perfect geek chic accessory.

Creating the Preppy Look

Most parents love to see their sons wear clothes that make them look like young men, even if your boy is too little to head off to an Ivy League college anytime soon. Try to help your son find the right preppy attire for him by experimenting with key pieces and mixing them up to create fun and distinctive outfits that will see him through to adulthood. After all, preppy clothes are classics which never go out of style.

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Types of Preppy Boys Clothes