How to Style Preppy Classics: Let’s talk about the return of prep and how to make it work for you! 

With the rise of quiet luxury in 2023, prep has made a comeback amongst trendsetters. Prep is the corner of the fashion world where style meets tradition. Contrasting the unbridled joy and punchy positivity of maximalism and dopamine dressing, preppy classics bring an air of timeless elegance and understated flair.  As Stacy London beautifully puts it, “Style is about the choices you make to create the aspect of yourself that you want to show to the world.” Your closet and wardrobe expression don’t have to keep to one aesthetic. Clothes are individual pieces that can be crafted into a million different styles. So let’s get into how to style preppy looks that embrace personal style! 

Moment of Honesty:

I am a clothes horse. I still have clothes from middle school that I still wear, like the very first cami I bought from Forever 21! On the flip side, right before I was diagnosed as bipolar, I GOT RID OF 85% OF MY WARDROBE in a manic episode. I still have pieces I mourn from that period. Due to that trauma, I never really get rid of items, except: 

1: The item no longer fits- dress for the size you are, not the size you want to be.

2: I haven’t worn it in 5 years. 

3: I have a friend or acquaintance who I know will love the item way more than I do. If you know me irl, you know I’m constantly passing things on. 

However, I also have a list of items to NEVER get rid of:

1: Keep your solid, classic items; think of a well-made blazer or a white button-down. 

2: Very unique Items. I have a few items that are such unique statements that I will always keep them! 

Nostalgia can go either way for me when it comes to my closet. The dress I wore to my dad’s funeral? I let it go a decade later. The dress I wore to marry Bill? I will keep it forever, not only for nostalgia’s sake but because I often re-wear it! This leads us to…

Re-wear is essential to having a solid, usable closet. 

Re-wear is key for two reasons. First, sustainability (we don’t need a new item for every life moment, be it brunch with the gals or a holiday gathering at the in-laws.) Second, re-wearing things is crucial in developing your personal style! Yes, you may dress like a princess one day and a business professional the next or maximalist to minimalist. Being able to wear the same dress for any event, aesthetic, or mood means that you have found a piece that genuinely expresses YOUR unique style. 

So, how do you style items outside your norm?

Do you ever find an item that you LOVE but is totally outside of your normal aesthetic or style? There’s no reason not to give them a go! 

Here are three ways to make a preppy item work for your personal style: 

1: How to Style Preppy Classics: Pick them with a twist. 

I have never had a preppy style. When I saw this blazer, I was instantly drawn to its mixed media factor. While the cut and plaid fabric is preppy and traditional, adding the denim insert and the corduroy cuffs gives it a maximalist twist! Blazers are great to play with because they are classics and are always in style. Always being in style means they are always being created in new iterations to keep up with trends. 2023/24 blazer trends update the classic to have ruffles, feathers, bright pink, and more. Plus, the 20-year trend cycle means it’s super easy to purchase this preppy classic second-hand! (Although, is the 20-year cycle even accurate anymore?!


2: How To Style Preppy Classics: Pair them with your current LOVES.

I would have felt like a schoolgirl if I had paired this blazer with a pleated skirt. If I had worn narrow jeans or knee-high boots, I would have felt like a horse girl! To style this in a Kait way, I chose camo pants to add my quintessential touch of print mix to the look. While a headband can also veer preppy, this black one adds a touch of maximalism with its padding and beading.

(I’d add a FOR YOUR PERUSAL here, but this one is incredibly personal and already in your closet!)

3: How To Style Preppy Classics: Add the unexpected.

Bright orange is not a color one associates with the prep aesthetic. Which, to me, makes it the perfect foil to cancel out any preppy vibes and make it more ME.

The best style is found in opposites- there is a reason print clashing is a micro trend! Think leather and lace, knit and denim, chiffon and tweed. Based on that philosophy, another way I would style this blazer is with a massive puffy dress! Perhaps, with a pair of balloon cargo pants like these, and then add pointed slingback kitten heels with a sparkle or even an embellishment like this red rose pair


Let’s Wrap It Up!

Preppy classics add the history and structure side of fashion with the delight and intentionality of personal style. Like styling any item, it’s about creating a look that’s not just visually appealing but also resonates with your very essence. Let any piece you style be a reflection of what that Stacy London describes: a story told without words and a journey of joyous self-expression.

How do you feel about preppy classics? Yay or nay? Is there an aesthetic that you total avoid? Lets discuss in the comments! 

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