What Should I Wear If My Style Is Preppy?

When I think of preppy style, my first thought is the clueless fashion era.  During this era, some of the trends that were very popular were mini front button skirts, plaid skirts & blazers, etc. 

Another popular show is Gossip Girl! Blair’s preppy style is definitely one of my favorite styles and one that should most definitely be highlighted.  Although preppy style did not originate from these movies & T.V shows I do think the styling in both the movie and the show, shows the variation of preppy style.
And If you think of some of the most classic 90a sitcoms such as Fresh Prince Of Bel-Air, Hilary’s style was definitely preppy. Also one of the most popular preppy girls was Whitley from A Different World.

There are multiple subcategories to preppy style and most of that is greatly based upon cultures and current trends. For example, in the 80s & 90s, the preppy style not only had the collegiate aspect, which is the crew necks and cardigans. But also you would notice the dramatic shoulders in blazers, layered pearls, etc.


If you check out gossip girl, you will also see the collegiate style, but also the preppy style including very feminine aspects.
Now fast forward to today, the preppy style has changed a lot with a lot of influence from past style preppy trends. But also, with a dose of current trends infused into the style as well.
With that being said, what makes the preppy style preppy. Is the collegiate style along with nautical influences.

To build an actual preppy wardrobe you are going to want to invest in the basic preppy wardrobe essentials such as Khaki Pants, Collared shirts, Mini Skirts, Cardigans, etc.

How do I know if my style is preppy?

  • You love nautical prints such as stripes , polka dots with notes of tropical patterns & prints.

  • You love colors that are bright, neutral earth tones or pastel.

  • You prefer your clothing to fit more tailored & structured

  • You love polo shirts & cardigans

  • You like your collars to be crisp and polished when you wear a blouse or button up.

  • You prefer to keep your shirts tucked in.

  • You love layering your blouses with a vest, cardigan or blazer.

  • You prefer your pants to be fitted rather than slouchy.

The Best Tops For Preppy Style

Shop This Button Down Here

Shop This Button Down Here

Preppy Collared Shirts- while they can look a bit classic, they can definitely become essential for a preppy wardrobe. I recommend layering a collarless blazer paired with a brown satchel bag and khaki pants to give this top a more preppy look.

Shop This Button Down Here

Shop This Blouse Here

Shop This Blouse Here

Preppy Feminine Blouses- if you are looking to go for that Blair, Gossip Girl preppy style, then a nice feminine blouse, styled with khakis or straight legs is the perfect option for you.

Shop This Top Here

Shop This Top Here

Henley  Shirts- when talking about the preppy style we often focus only on the staple preppy items. But the base of your wardrobe is really going to contribute to that preppy look. You can style this Henley top underneath a button-up, cardigan, or blazer.

Shop This Top Here

Shop This Top Here

Shop This Top Here

Crew Neck- if Henley tops aren’t your thing, the. You can always opt for a crew neck. 
Shop This Top Here

The Best Jackets For Preppy Style

Shop this preppy collarless blazer here

Shop this preppy collarless blazer here

Collarless Blazer- a signature piece inside of a preppy wardrobe is definitely a collarless blazer. You can even go further by adding a fun button to it.

Shop this preppy collarless blazer here

Shop the jacket here

Shop the jacket here

Utility Jacket- A utility jacket could easily be paired with a pair of khakis, a striped button-down, or even a Henley top. Add a pair of loafers and a satchel handbag to really bring forth that preppy-inspired look.

Shop the jacket here

Shop The Trench Coat Here

Shop The Trench Coat Here

Trench Coat- one of Blair Waldorf’s signature coats was definitely a trench coat. Of course, if you do not like the more traditional trench coat, you can always go for one with some sort of wow factor included.

Shop The Trench Coat Here

The Best Pants & Shorts  For Preppy Style

Shop these pants here

Shop these pants here

Khaki Pants- Khaki pants are definitely a must-have essential to really make sure your wardrobe reflects that preppy look. 
Shop these pants here

Shop these shorts here

Shop these shorts here

Bermuda Shorts- the preppy look doesn’t really consist of a lot of tight-fitting shorts. Bermuda shorts are a perfect balance, you can also grab a pair of Bermuda shorts in denim rather than just khaki.

Shop these shorts here

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Shop these jeans here

Classic Jeans- every wardrobe needs a pair of classic jeans. These jeans could easily be paired with each top or jacket that I’ve included above.

Shop these jeans here

The Best  Dresses And Skirts And Dresses For Preppy Style

Shop this dress here

Shop this dress here

Nautical Maxi Dress- one of the key themes within the preppy style is that whole nautical vibe. 

Shop this dress here

Shop this cotton eyelet dress here

Shop this cotton eyelet dress here

Collar Dress-another preppy wardrobe essential, pair this dress with a pair of loafers that compliments the color of the dress.

Shop this cotton eyelet dress here

Shop this skirt here

Shop this skirt here

Tweed Mini Skirts- you may have seen this style of skirt throughout the 90s. And if your style leans more towards a girly preppy style, this is a great style of skirt to add to your wardrobe.

Shop this skirt here

Shop this mini skirt here

Shop this mini skirt here

Khaki Front Button  Skirt- This skirt can easily be paired with a button-up layered with a cardigan and loafers.

Shop this mini skirt here

Stylish Preppy Shoes

Shop these shoes here

Shop these shoes here

Preppy Women’s Loafers- These loafers can easily be paired with a smock dress, Bermuda shorts or a basic pair of jeans.

Shop these shoes here

Shop these preppy flats here


Shop these preppy flats
here

Preppy Flats- while loafers may not be your thing and you still have that preppy style, then pointed-toe flats are also a great replacement.


Shop these preppy flats
here

shop these pointed toe boots here

shop these pointed toe boots here

Preppy Pointed Toe Boots- are a must-have for your preppy wardrobe. You can pair them with a classic pair of jeans, a button-down or basic tee, and a crossbody bag.

Shop these pointed toe boots here

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