Originated among rich kids who venerated an expensive lifestyle and status symbol, preppy fashion has become popular after being featured in many movies and TV series. Many young people fell in love with this style.

Preppy men’s fashion features many iconic elements, which still endures today and you surely already have in your wardrobe. In other words, embracing your preppy soul and playing with new looks will be easy and funny.

Looking for some inspiration? We have a few ideas to spice your style up.

The Idea Behind Preppy Style

Being preppy means finding the perfect approach to a unique and personal style, rather than focusing on a prescriptive set of pieces of clothing. When experimenting with new fashion, the pioneers of preppy style were looking for a way for being always dressed up for casual situations, but also on point for any formal setting.

In other words, a good prep should be able to change his dress code with dynamicity. You should never be too elegant, but you should also avoid a lazy, last-minute-casual style.

This may sound a little confusing, but it all makes sense once you realise that the style became particularly mainstream in the 1980s, where young people were continually experimenting with new styles, trying to express their personality.

The only rule is to never go full preppy style. You don’t need to incorporate all accessories or elements of this fashion style at once. Otherwise, you will just look overdressed. What you want is to look effortlessly stylish and fabulous on any occasion.

The Perfect Preppy Men’s Wardrobe

Madras Shirt

The madras shirt is one of the most iconic elements of the preppy style. Back in the 1980s, it was a proper status symbol for those who could afford to travel and wear exotic pieces of clothing. The best accessory? Your attitude.

Photo by Tommy Hilfiger (Madras Check Short Sleeve Shirt)

Boat Shoes and Loafers

You don’t need to own a boat to wear classy shoes. Loafers and boat shoes are comfortable and will immediately let everybody know that you have very good taste. You can pair them with a suit, or even with your favourite chinos in summer. Of course, they must be worn sockless.

Photo by M&S (Leather Deck Shoes)
Photo by M&S (Leather Deck Shoes)

Braided Belt

A leather braided belt is the best way to hold up your pants with style. A brown belt with a brass buckle will give you all the 1980s Ivy League vibes you need.

Photo by Trendhim (Collin Rowe, Cognac Braided Belt)
Photo by Trendhim (Collin Rowe, Cognac Braided Belt)

Oxford Cotton Button-Down Shirt

Only the best pupils could study at Oxford University. However, nowadays, everyone can wear an Oxford shirt, inspired by polo players. Pair it with some jeans or cotton pants, and your favourite boat shoes or loafers.

Photo by PPG Workwear (Disley Men’s Oxford Shirt with Button Down Collar)
Photo by PPG Workwear (Disley Men’s Oxford Shirt with Button Down Collar)

Critter Print

Shirts, belts, wallets, neckties, and many others: critter tie is the perfect choice for any of your accessories. Just don’t confuse it with animal print, as critter patterns usually feature silhouettes of different creatures.

The Blazer

Nothing shouts businessman or businesswoman like a blazer. This is one of the pillars of the preppy look, although contemporary men’s fashion has transformed it into a more casual piece. You can wear it with your suit, or even your favourite metal band t-shirt.

Cable-Knit Varsity Sweater

Inspired by the Ivy League, cable knits were used by those who played tennis. Today, it is an iconic, athletic piece of clothing. Style your sweater with a pair of jeans and a simple shirt for a timeless look.

Tweed Coats

Harris Tweed developed the perfect coat for the rainy English countryside. We recommend investing in a good coat, made of 100% pure virgin wool, which will last for many years and give any of your looks a stylish and elegant twist.

Photo by Brook Taverner (Breedon Pure New Wool Check Jacket)
Photo by Brook Taverner (Breedon Pure New Wool Check Jacket)

“Go to Hell” Pants

Any boldly coloured pair of trousers is considered a “go to hell” pants, which are worn to express one’s attitude. Wearing very bright colours may not be everybody’s cup of tea, but you should give it a try. Play with some pants and a white, plain shirt to find your bold style!

Photo by Debenhams (Maine New England, Dark Yellow Tailored Fit Chinos)
Photo by Debenhams (Maine New England, Dark Yellow Tailored Fit Chinos)

Polos

Ralph Lauren is just one of the many brands who became popular thanks to their polos. This piece of clothing is the perfect “smart casual” addition to any wardrobe, meaning that it can be worn with basically any outfit. Feeling bold? Rock a polo shirt with a critter print!

Pullovers

Pullovers are an immediate go-to for any look. For example, they are the perfect office or casual piece when paired with some chinos. Otherwise, you can rock them on a date with a pair of cosy jeans or some cotton pants. The best thing? They will keep you warm during colder months.

Photo by Samuel Windsor (Aran Knit Jumper in Mushroom)
Photo by Samuel Windsor (Aran Knit Jumper in Mushroom)

Knitted Ties

Knitted ties are a versatile accessory, perfect for when a tie is required, but you want to keep your style unconventional and unique. They look particularly good with a cable-knit or a button-down shirt. Forget about the blazer, as the tie will be the protagonist of your outfit.

Photo by Grand Frank (Blue Zigzag Knitted Tie)
Photo by Grand Frank (Blue Zigzag Knitted Tie)

Bowties

Bowties are perfect for those who don’t like ties or prefer a more unconventional accessory. Unless you are going to a wedding party, try not to wear any suit with your bowtie. In fact, you should play with a more casual and preppy style.

Photo by Pink Shirt Maker (Velvet Bow Tie in Deep Red)

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