My Classic & Chic Preppy Wardrobe Staples

I’ve always loved preppy style. Even growing up, I had a thing for polos and thought I was very cool walking into the Ralph Lauren Polo outlet in Park City– never mind that I couldn’t actually afford anything. There’s just something about the crisp and classy look, the way it toes the line between polished and laid-back.

Now that I live in the South, preppy style feels second nature. It’s more normalized here than it ever was back in Utah, and in summer especially– it just fits: breezy tops, sun-faded colors, and easy silhouettes that still look put together. It’s timeless without feeling stuffy– and when you get it right, it’s the most effortlessly elevated version of everyday style.

Where It All Started

Preppy style originally came from East Coast prep schools and Ivy League campuses, where uniforms and sportswear started blending into personal style. It was about dressing for tennis, sailing, or dinner at the club– but it stuck around because it looked good without trying too hard. While I was accepted to Cornell and U Penn, I didn’t go there, but man, I feel like I would have loved their style in the early 2000s.

What “Preppy Style” Really Means

To me, preppy style is all about a certain kind of ease. It gives off old-money energy without being flashy. It’s tailored but never tight. Structured but still soft. And the updated version is so much more wearable. A linen blazer over a tank and shorts? A collared shirt thrown on over a swimsuit? That’s my kind of summer prep.

5 Must-Haves for a Preppy Wardrobe

1. Polo Shirts

They’re back– and not in a dad-on-the-golf-course kind of way. I love cropped polo or sleeveless versions paired with high-rise shorts (I styled this polo look here) or casual tennis skirts. If I’m golfing, I opt for a more athletic material, but if I’m wearing it casually, I opt for cotton or cotton blend fabrics.

If you want a polo that looks good both on and off the golf course, buy A. Putnum polos. They make some of my very favorite golf clothes because they look like classic preppy style but they’re still functional on the course. I put together a roundup of super cute golf outfits in this post.

2. Oxford Button-Down

Always in rotation. In the warmer months, I wear this oxford button-down half-tucked into chino shorts or tied at the waist over a dress. It’s timeless, polished, and effortlessly chic with a structured collar and classic silhouette. The soft cotton fabric keeps things relaxed and easy. Slip on classic leather sandals and simple gold jewelry to finish the look!

3. Cardigans: The Polished Layer You’ll Actually Wear

Cardigans are one of those timeless pieces that quietly do a lot. They’re preppy by nature– classic, neat, and easy to layer. I love a lightweight cotton cardigan in the summer, either worn over a simple tank or tied over the shoulders with a sundress or oxford shirt. You can button it all the way up for a clean, tailored look, leave a few buttons undone at the top for a more relaxed feel, or even unbutton the bottom to show off high-waisted shorts or a belt. For a more traditional vibe, you can’t go wrong with a cable knit cardigan or a cropped version paired with a pleated skirt. Whether you wear it or drape it, a cardigan always makes an outfit feel a little more intentional.

4. The Navy Blazer

A year-round hero, but especially great for summer nights. I’ll toss a navy blazer over my shoulders with a dress (probably from this list of my favorite Tuckernuck dresses) or wear it with white denim shorts to dress things up without trying too hard. The structured fit keeps it polished, while the deep navy hue adds a relaxed sophistication that works no matter the season.

5. Chinos, GTH Pants & Nantucket Reds

Chinos, GTH pants, and Nantucket Reds are undeniably preppy– but I’ll be honest, I don’t reach for them often because I just don’t have the time to iron. However, pre-kids I owned chino shorts in every single color that J.Crew sold. (My husband, on the other hand, lives in chino shorts from Duck Head.)

Other classic bottoms are GTH (Go To Hell) pants, which are bold, bright, and surprisingly wearable if you keep everything else simple. And Nantucket Reds? The washed-out pinkish red screams summer vacation.

Light Summer Layers and Linen everything

Linen is another summer preppy essential– it’s relaxed, breathable, and still feels polished. It gives off that effortless “I summer on the coast” energy, even if you’re just running errands. I constantly reach for linen button-downs this time of year, whether layering one over a swimsuit (these are the most flattering mom-friendly suits) or pairing it with chino shorts. 

A linen blazer is another go-to: structured enough to pull a look together, but still relaxed and easy. I also love linen pants with a tucked-in polo or a crisp oxford button-down for a look that’s classic without feeling stiff. Wrinkles? Part of the charm. 

Even in the South, we get those evenings where a light sweater just feels right.

• Argyle & Cable Knit Sweaters: Cotton or lightweight versions only. I love them tied over my shoulders for a laid-back touch.
  
• Tennis & Cricket Sweaters: Perfect over a mini or styled with shorts.
  
• Rugby Shirts: Oversized and worn as a cover-up or tucked into cutoffs? So cute.

A ton of my go-to linen pieces and classic wardrobe staples are from Frank & Eileen, and I also put together a realistic styling guide for linen pants.

Shoes That Ground the Look

• Boat Shoes: I know they’re classic, but I save them for beach days or pairing with white shorts.
  
• Loafers: Always polished. I wear mine with everything from sundresses to chinos. They’re by far one of my most-worn shoes since they elevate any look. (These are in my roundup of the most comfortable and cute work shoes.)
  
• White Sneakers: The most versatile. Clean and classic. These are the 9 best white sneakers.

Accessories & Extras: Belts, Bags, and Sunglasses

The right accessories keep preppy style feeling polished without going overboard. A classic belt– whether it’s canvas, leather, or striped– pulls everything together. Structured handbags and top-handle totes always work, and I love pairing them with timeless sunglasses (think tortoiseshell or aviators) for that clean, pulled-together look.

Seersucker & Sporty Details

Seersucker is a summer classic for a reason– it’s breezy, breathable, and always feels fresh. I’m also a big fan of tennis-inspired pieces like pleated skirts, sporty collars, and anything that looks like it could double as resort wear. 

How to dress preppy but on trend

• Learn the Classics: Once you know the staple pieces, it’s easy to mix and match.
  
• Play with Color & Print: I stick to mostly neutrals and pastels with the occasional bold stripe or embroidery.
  
• Mix Casual with Tailored: Like a polo with linen shorts or a blazer over a cotton tank.
  
• Modern Accessories: I keep my sunglasses, bags, and jewelry updated to avoid looking too vintage.

Preppy Style: The Do’s and Don’ts

Do:

• Invest in quality pieces
  
• Embrace structured fits
  
• Add color intentionally
  

Don’t:

• Dress like you’re headed to a costume party
  
• Overdo the accessories
  
• Forget to make it you

Shop The Post