The new decade has begun and no one style has taken control yet. Although, one trend in particular, the preppy look, has seen a resurgence. The traditional ivy style came into its own in the 1940s, primarily for those who attended ivy league universities. Since then, however, the style has become an option for anyone interested in a classic look for any occasion. Today, we’re breaking down some staple pieces for a preppy wardrobe and some of the best adaptations of the style over the decades.

The Art of Oxford Shirt

In the world of collared shirts, there are so many choices: dress shirts, button-downs, button-ups, flannels, polos and the list goes on. We’ll keep it simple for you: oxford cloth button down. This is a type of shirt with a medium thickness, clean fit and universally respectable style. 

This is not to say certain flannels or polos won’t work great in your wardrobe, but err on the side of caution with those routes. For example, bright pastel polos will give you more of a frat boy look, which is not to be confused with the traditional ivy look. Similarly, bulky flannels will come off more skater/grunge and less so preppy.

The Right Footwear

Most people will assume the look is as simple as dress shoes. Wrong. There are many routes to nailing the preppy look without throwing on those clunky, glossy abominations you bought years ago for a wedding. First, there are loafers. When picking out a pair of loafers, stick to neutral colors like dark blues, grays and browns. Go with a suede material for summertime and something more durable like leather for colder months.

Oxford shoes are another solid choice. These come in many different styles such as laces, monk straps, broguing, pointed, and so on. It’s best to try some pairs on in store to find what works for you, instead of just picking online.

If loafers and oxfords aren’t your speed, you can opt for a plain canvas shoe. When it comes to a preppy style, white canvas sneakers can’t be beat. For the look as a whole, the less graphics, the better. The frontrunners for a versatile sneaker for any preppy look are: Common Projects Achilles Lows, Nike Killshots and Adidas Stan Smiths.

The Outerwear

Layering is one of the more crucial aspects of the preppy look. An easy way to get started is as simple as throwing a sweater over your button-up. By sweater, we mean a jumper or v-neck sweater. Some styles include cable knit, fisherman or waffle knit. We advise against the notorious sweater vest.

Jackets and coats are a much broader category when it comes to this style. There are two cardinal rules: avoid hoodies and think about silhouettes. By silhouettes, we mean how the outerwear will fit you over all of your layers and what shape it will give you. You don’t want to go too tight or too big when it comes to coats, because it can ruin the whole look. Something like a pea coat can often be too dressy for a casual look, but something like a duster will work better. For jackets, we encourage you to find a letterman or bomber that will fit nicely over your bottom layers. 

Thrift stores are your best friend for finding the right outerwear since it’ll often be real vintage pieces at much lower costs than the big brands that are upcharging you for a vintage look. Don’t be afraid to buy something a little loose and take it to a dry cleaner or tailor to get it altered just for you.

The Pants

When it comes to a preppy style, there is no room for jeans or joggers. The choices are chinos, slacks and khakis. Slim/skinny are not typical fits for a traditional preppy style, but the look works best when you make it your own. Straight fit is the optimal choice, but some preppy purists embrace the relaxed fit of the 1940s.

Our Favorite Looks

Kanye West puts a preppy twist on his late 2000s streetwear look by pairing it with a varsity jacket. Along with the baggy jeans and bulky Jordans, Kanye manages to pull off a collegiate streetwear fit.

Brad Pritt pulls off the sweater/button-up look effortlessly in this GQ shoot. He’s not afraid to play with brighter colors and a toweling material, and it comes out as a classically preppy fit.

Our last spot goes to Chris Paul, an established style icon in the NBA. When it’s time to dress up, maintaining that preppy style can become difficult as you start to get into basic formal wear. For Paul, he skips the tie and opts for a patterned shirt and handkerchief to look just as dressy without abandoning that playfulness of the preppy style.