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Preppy Style: How to Master the Look This Fall and Winter

Posted September 11 2019

When it comes to fashion, nothing says classic, crisp and classy like the preppy style. Defined by chinos, blazers, crewneck sweaters, refined accessories, and loafers, this look is as American as it gets. The preppy look is truly aspirational with conservative cuts, fine fabrics, and timeless accessories, one of the reasons why it’s not so easy to pull off.

The classic Prep style was born on the campuses of Ivy League colleges and East Coast Prep Schools. Brands such as Ralph Lauren, Brooks Brothers and Lacoste ruled the prep style world, fabricating the timeless styles and cuts of the prep-set. 

If you are looking to turn yourself into an amazing prepster this coming fall and winter, we have you covered with some cool tips that will help you achieve this much-desired look.

Now, there is so much that needs to go into consideration when coming up with stylish preppy outfits for both men and women. This guide will help you figure out these considerations, among other things. Let’s dive right into it.

Preppy Outfits Tips for Women

Preppy outfits are almost exclusively styled for men. But when styled correctly, they tend to bring out the best in Women. Here are a few tips for rocking this look.

Blouses, Blouses, Blouses

When it comes to preppy outfits for women, blouses can never be enough. The thing is, blouses are feminine, flowy and super delicate, which makes them a staple for this more conservative fashion style. They come in a wide variety of styles, from long and short-sleeved, to patterned, flowered, plain, subdued, and downright colorful.

This makes it easy to fit a blouse into any preppy outfit. Some of the looks you can easily pull off with a blouse include wearing a collared blouse underneath a sweater, or a blouse with a big bow tie.

You can pair these with corduroys or pencil skirts for casual or official looks. Your clothes say a lot about you and this look can help you make a statement.

The Perfect Shoe Types

Preppy shoes are simple but elegant enough to complete your look and make you feel awesome. Some of the best shoes for preppy outfits for women include the mary jane heels. They are versatile, comfortable, and go with almost anything from jeans, sheath dresses, slacks, blazer outfits, and more.

Ballet flats are the next best thing as they go with almost any preppy outfit without any effort at all. The upside of ballet shoes is that they come in a wide array of colors and patterns.

Loafers and oxfords are perfect if you want to pull off the British boarding school vibe. These may not be suitable for winter, but they are well suited for fall; and pair very well with jeans, slacks, and skits. Choose from a classic light brown to go with everything in your closet, or a bright red or leopard print to add some excitement. 

This list would not be complete without boat shoes! Boat shoes are great for casual preppy outfits for women. The perfect companion for boating, walking around town, and everything in between. A classic style shoe that has lasted the test of time. 

Style Patterns

You may not know this but patterns play a huge role in preppy outfits. For women, colors such as nudes, whites, pinks, and navy are the most common. Patterns include florals, plaid, polka dots and stripes, all common on skirts, pants, tops, and even accessories.

It’s easy to pull off a bold look with patterned dresses too. For a perfectly preppy outfit balance, match patterns clothing with plain colors. The navy & white stripe combo is perhaps the most famous “pattern” in the world of prep. Some even consider it a solid, as it is so prevalent and worn all year round. Stripes have evolved from boat neck tees, to chunky knit sweaters, to pleated silk dresses. 

Preppy Outfit Colors

We may have mentioned some basic colors above, but for a preppy outfit, it’s almost limitless. You can pull off yellows, red, green, blue, and pink just as well. Take a page out of Prep Queen bee Lilly Pulitzer’s book and splash a colorful print on an ensemble. You will look and feel happy instantly. 

Patterns, prints and colors are all great - but what about a critter embroidery! Your beloved golden retriever, favorite martini cocktail, or holiday motif will have you making friends and inside jokes everywhere this fall and holiday season. 

The Accessories

Now, for the best part of a preppy outfit for women, the look cannot be complete without the right accessories. To begin with, pearls are the jewelry to go with. Hats and headbands are a common pair. Then add light scarves, dainty wristwatches, and tights to complete a perfect look. Very Jackie O and Blair Waldorf. 

Preppy Outfits Tips for Men

Men are not left out in this trend, but actually the main feature. All preppy styles derive from Menswear: corduroys, sweaters, loafers. The preppy style is definitely one to make you stand out. Here are a few tips for men who want to rock this look.

Preppy Style Shirts

One of the most quintessential preppy style elements is the button-down shirt, especially when worn as a business casual outfit. Polo shirts are best suited for less formal outfits though they also hold great for formal events as well.

Collared polo shirts are some of the signs that you are prep. A formal ensemble with the button-down shirt will require a necktie, but ditching the tie and replacing it with a sweater can get you a more casual look.

For a refreshing and novel preppy look, go with the seersucker shirt. It comes off pretty fine for a formal look, especially when tucked in. Perfect for hotter summer days, and may we be so bold as to suggest a full seersucker suit!?

Preppy Style Sweaters and Blazers

Sweaters are the epitome of preppy outfits for men. Over shirts, under blazers, tied around your shoulders. Choose from classic crew-neck , v-neck, cable knit or a cardigan. All sweater options look exemplary when paired with the button-down oxford shirt and a nice tie.

The best fabrics when it comes to sweaters are cotton, cashmere, and wool. Solid colors will carry you through the years, but argyle prints and stripes are fun ways to jazz up your routine. 

Blazers are synonymous with the preppy style, especially the timeless navy blazer, that always comes off fantastic. The reason why solid navy is such a common choice is the fact that it comes off as smart and nautical. Single-breasted blazers with gold buttons embody the preppy style perfectly and pocket squares make them look even better.

There is a wide variety of materials to pick from, such as wool and poplin. A tweed blazer is sharp for Fall, and exudes the collegiate prep style of yore. Throw on a bow tie and oxford shoes and you will be sure to impress. 

Chinos and Go to Hell Pants

Nothing screams preppy like chinos. Chinos need to be well-fitting and go well with the oxford shirt. You can pull them off with either sweater or blazer, which makes them a great preppy outfit choice. Throw a cuff in the hem to show off your bare ankles and loafers look. The sweater will be a good option for winter so as to keep warm, but the blazer can take fall. 

Go to hell pants are for the bold, and they need some courage to pull off. But if you feel you are up to it this fall, then why not? Have a little fun with clothing. 

They come in bright colors such as green, yellow and red with loud, audacious patterns. If you wear these, then tone down the rest of the outfit to achieve some semblance to the overall look. Critter pants are the epitome of this style, and you can pick one that fits your interests or events. Holiday themed embroideries tend to be the hit of all parties. 

Preppy Shoes for Men

Your shoes are the conversation setter for your outfit so you need to get this right. Loafers are the first choice as they are light, super comfortable and easy to match with anything.

The Penny Loafer is an incredible choice for your Fall escapades. Boat shoes are the next best thing and they also go well with pretty much any preppy outfit. The Bridle Bit Driver is perhaps the most iconic shoe - good for wear all seasons, and they will never go out of style. Popularized by Gucci, the bridle or horse bit ornament has become a status symbol, and a coveted look at that. 

For the Accessories

Preppy styles require bold and colorful accessories. The conventional collegiate rep stripe ties are great, but you can also go with plaid or madras ties, animal print silk ties, and knit ties. 

For a book or work bag, stick with a light or dark brown. Add your heat stamped monogram for a uber prep touch. Socks are necessary at some point in the colder months, so opt for a classic stripe or fun motif to get you through the work day. 

Choose a Preppy Style to Stand Out

These are some of the key elements of pulling off an incredible preppy outfit. At this point, it’s pretty clear that the preppy style will never go out of date so how about you try it yourself the next season!

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