Prepster Essentials

While I can’t exactly define to you what being “preppy” even means, I know it when I see it. It’s seer sucker Oxfords, boat shoes, and jeans that fit just right. It’s all about classic things that never really go out of style. For that reason, I think it’s so essential that everyone owns a few preppy pieces of their own, no matter their sense of style.

Let’s talk about the classic button-up, or Oxford as I like to call it. Though it seems rather masculine when you first put it on, some proper tailoring makes all the difference. If your clothes fit just right, you’ll look so much more put together. Oxfords are the most versatile part of your wardrobe. They can be worn with a statement necklace and chinos in the summer, or a sweater and leggings in the winter. I love to get a few basic colors, such as blue, white, and light blue and white stripped, to switch it up. Quality ones may be a little expensive, but they’ll last you ages! Plus, you don’t always have to shell out serious cash for one. It’s not about the little logo embroidered on, but how great it fits.

Everyone wears jeans. Nearly every store sells jeans. With this in mind, one would think finding skinny jeans that fit well would be easy. Sadly, they are mistaken. I usually end up finding the perfect fit in the waist, but too much length. Rather than splurging on jeans I’m going to end up stretching out, I simply cuff the ankles for the perfect fit. This allows me to roll them to hit right above the ankle for a typical length, or mid calf for some DIY, no commitment capris. Skinny jeans go great with duck boots, Converse, riding boots, or boat shoes on a fall day.

Since somehow we ended up moving from head to toe, why don’t we talk about the ideal slip on shoe. Whether yours takes the form of a boat shoe, or Sperry dock shoe, slip ons are the best! They usually come in neutral colors, which make them ideal for mixing and matching with outfits. It always feels like I’m running out the door, so in a rush it’s great to be able to slide something on without remembering to grab socks. They also seem to be multi-seasonal. I tend to wear mine from spring into fall.

I’ve crafted a very basic outfit for you that can be dressed up or down. Each piece can be styled in hundreds of ways based on your accessories. I love playing around with this combination! Let me see how you jazz it up by commenting below or tagging me on Instagram (@classygirlinawhirl).

Stay Classy,


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