How To Be Preppy: Mastering the Timeless, Polished Aesthetic
, by Lewkin Unnie, 6 min reading time
There’s just something about preppy outfits that hit different. They’re polished, clean, and somehow make you look like you’ve got your life together, even if you don’t. And honestly? That’s the kind of energy we’re bringing this season.
At Lewkin, we’re all about putting our own spin on preppy. It’s not about following the rules — it’s about taking those timeless staples and making them feel fresh. Pleated skirts, oversized blazers, and layered looks that mix classic vibes with modern flair? Say less.
Let’s show you how it’s done.
What Is the Preppy Aesthetic?
First things first, what’s the deal with preppy style anyway? This iconic aesthetic started in the Ivy League schools of the early 1900s, where tailored blazers, crisp shirts, and pleated skirts weren’t just a look — they were a whole lifestyle.
Grounded in classic, polished threads, the preppy scene's always been about lookin' cool as a cucumber and put-together, regardless of where the day takes you. Over the decades, preppy has evolved from campus uniforms to a global fashion staple.
Today, it’s not just about tennis skirts and sweater vests (though we love those). It’s about mixing timeless pieces with modern details — like oversized blazers paired with chunky sneakers or layering collared shirts under trendy sweatshirts. It’s refined but never boring.
Why Is Preppy Trending?
So, why is preppy suddenly everywhere again? Spoiler alert: it never really left, but here’s why it’s blowing up right now:
- Nostalgia is in.Vintage-inspired looks are huge, and preppy fashion brings all the old-school feels with a modern twist.
- It’s versatile. Preppy staples like tailored blazers, pleated skirts, and loafers go with everything, from casual fits to dressed-up looks.
- Social media glow-up. TikTok and Instagram are packed with preppy outfit inspo that makes you want to throw on a cable-knit sweater immediately.
- It screams confidence. Let’s be real — nothing says “I have my life together” like a perfectly styled preppy outfit.
- It’s sustainable. Preppy pieces are timeless, meaning you can invest in quality staples and rework them season after season.
In short, preppy is trending because it’s classic, chic, and totally adaptable to your mood. And if you ask us, it’s proof that polished looks don’t have to feel outdated — they just need a little remix.
Tips for Nailing the Preppy Look
Ready to turn heads in a way that says, “I’ve got it all together” without actually trying? Preppy is where it’s at. It’s clean, classic, and gives you instant main character energy.
Here’s how to pull it off while still keeping it fresh and totally you.
Boss-Level Office Looks
Preppy for the office doesn’t mean boring. Start with our Oversized Ribbon Midi Blazer layered over the Collar Striped Button-Up Crop Shirt. Add the Cotton Pleated Mini Skirt or some tailored trousers, and finish with sleek loafers or ankle boots. It’s the kind of outfit that says, “Yes, I’ve got this,” even if you don’t have your coffee yet.
Effortlessly Polished
Want to look like you casually woke up stylish? Grab our Button-Up Long Sleeve Solid Blouse and pair it with high-waisted trousers or chinos. Let it hang loose, or go for a half-tuck. Throw on your go-to sneakers, and just like that, you’re ready for a chill day that still screams effortlessly cool.
Brunch Goals
If your weekend plans include mimosas, go for our Graphic Lettering Round Neck Knit Sweater with the Waist Banding Pleated Mini Skirt. It’s comfy, cute, and perfectly preppy. Add ballet flats or loafers, toss your essentials in a tote bag, and you’ve got the ultimate "I woke up like this" brunch look.
Evening Upgrade
Night out? Try the Crop Wide Collar Vest with our Checkered Pleated Mini Skirt for a dressed-up look that’s still fun. Add some gold hoops, heeled boots, and maybe a bold lip. Or, if subtle is more your thing, the Solid Two Layered Pleated Midi Skirt paired with our Fuzzy V-Neck Button Short Sleeve Sweater is quietly chic without overdoing it.
Outdoors, but Cute
For those park days or errand runs, start with our Double Pocket Pleated Mini Skirt and a fitted tee. Layer on a denim jacket, lace up some comfy loafers or boots, and you’re ready to head out. It’s simple, but it looks like you put in way more effort than you actually did.
Fall Layers
Nothing beats preppy layering in the fall. A Vintage Oversized Checkered Blazer over a button-down shirt with one of our snazzy Denim Skirts is the move. Add tights and ankle boots, and you’ve got an outfit that works for everything from pumpkin patch photos to grabbing lattes with friends.
Cold-Weather Ready
Winter doesn’t mean you have to sacrifice style. Layer our Glossy Puffer Vest over a Striped Cotton U-Neck Long Sleeve Tee and add dark jeans or a mini skirt with tights. Top it off with a scarf and cute boots, and boom — you’re warm, cozy, and still look like you’ve got your life together.
Prep It Up With Lewkin
So, preppy looks are having a moment, and honestly, it’s about time. They’re crisp, versatile, and perfect for literally any plan you’ve got going on. From layered fall fits to polished summer vibes, preppy style somehow makes you look like you’ve got your whole life together, even if your coffee is still doing the heavy lifting.
At Lewkin, we’re all about taking this classic aesthetic and adding a modern twist. Think timeless pieces, fresh silhouettes, and a little extra edge. The result? Preppy looks that feel just as at home on campus as they do on your Insta feed.
Let’s make this aesthetic yours.
Sources:
How 'Ivy' clothes became a century-spanning fashion mainstay | Marketplace
Why Nostalgia Has Become A Popular Trend Today? | University of Computer Sciene and Technology
How Preppy Style Has Evolved Through the Decades | InStyle
Timeless iconic fashion buys – Pieces that never go out of style | Harpers Bazaar
