The Real Chic Life

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The Chic Guide to Mixing Preppy Style With Your Personal Style

Preppy style is having a moment again. We’ve covered preppy style before (for an intro to preppy style check out The Real Chic Guide to Preppy Style and The Real Chic Guide to Preppy Fall Style)—and this fashion aesthetic is technically timeless, but for fall 2026, it’s bigger than ever.

From collegiate-inspired knits and rugby shirts to loafers, pleated skirts, cable-knit sweaters, blazers, and button-downs, the runways and street style are embracing the academic side of fashion. The current interpretation of prep is also a little more relaxed and modern than the perfectly coordinated prep of decades past.

And I think that’s the best way to wear it. You don’t need to go all in on perfectly preppy style (unless you want to of course). The trick to making preppy style feel chic is to mix it with your existing wardrobe and the pieces that make you feel most like yourself. So think of preppy pieces as ingredients—not a uniform.

You can add a little prep to a romantic wardrobe, make minimalist style feel more polished, give edgy outfits a classic twist, or bring a little structure to a bohemian look.

Here’s how to do it (click the photos to shop).

First, Know Your Preppy Building Blocks

You don’t need all of these pieces. In fact, you probably shouldn’t buy all of them.

Choose the ones that naturally fit your wardrobe.

Classic preppy staples include:

  • Cable-knit sweaters
  • Cardigans
  • Oxford shirts
  • Striped Breton tops
  • Rugby shirts
  • Polo shirts
  • Pleated trousers
  • Pleated skirts
  • Loafers
  • Mary Janes
  • Penny loafers
  • Blazers
  • Crewneck sweaters
  • Argyle
  • Fair Isle knits
  • Varsity-inspired jackets
  • Tartan and plaid
  • Sweater vests
  • Riding boots

For fall 2026, the easiest way to participate in the trend is to choose one or two preppy pieces and let the rest of your outfit reflect your own aesthetic.

That’s what keeps it personal.

If Your Style Is Classic

This is the easiest combination because classic and preppy naturally speak the same language.

Try a navy blazer with straight-leg jeans, a cashmere crewneck with tailored trousers, or a button-down shirt underneath a simple sweater.

The key is keeping everything polished without becoming overly coordinated.

Try:
Navy blazer + white tee + straight-leg jeans + loafers

A woman wearing a navy double-breasted blazer with gold buttons, paired with a white shirt and dark jeans, standing against a light background.
Plain white short-sleeve t-shirt with a round neckline and COS label.
A model wearing high-waisted blue jeans paired with a dark sweater and black high-heeled shoes, standing against a neutral background.
Side view of a stylish brown leather loafer shoe with a low block heel and decorative stitching.

Or:

Cable-knit sweater + tailored trousers + leather belt + loafers

Close-up of a person wearing a ribbed blue sweater with a cable knit pattern.
A person standing in tailored gray trousers with a high waist and pleats, paired with a light-colored, long-sleeved shirt and metallic shoes, against a neutral background.
A black leather belt with a gold buckle and several adjustment holes.
A pair of black leather loafers with a classic design, featuring a stitched detailing along the edges and a low heel.

Your goal is quietly polished, not school uniform

If Your Style Is Feminine or Romantic

This is one of my favorite ways to wear prep.

Take traditionally feminine pieces—silk blouses, floral dresses, skirts, bows, pearls—and pair them with something slightly collegiate.

A pleated skirt with a fitted cardigan feels sweet without being overly girly. A floral dress with loafers or Mary Janes feels current. A pearl necklace instantly makes a rugby shirt feel more feminine.

Try:
Floral midi dress + loafers or mary janes + cardigan draped over the shoulders

A model wearing a black floral dress with red and white patterns, posing against a neutral background.
A pair of black leather ballet flats with a Mary Jane strap.
A woman wearing a red cable-knit cardigan with buttons, sitting against a neutral background.

Or:

Pleated skirt + fitted cashmere sweater + pearl earrings + riding boots

A close-up of a woman wearing a beige ribbed sweater and a brown pleated skirt.
A woman wearing a light beige long-sleeve sweater paired with light-colored trousers, standing against a plain background.
Close-up of gold hoop earrings featuring a white pearl drop.
A pair of stylish, tall brown leather boots with a sleek design and a low heel.

The contrast is what makes it interesting.

If Your Style Is Minimalist

Preppy pieces work beautifully in a minimalist wardrobe because so many of them have clean, simple silhouettes.

Stick to a restrained color palette—navy, cream, camel, gray, black, burgundy—and focus on texture and proportion.

A simple navy crewneck over a white shirt can be enough.

Try:
White button-down + navy sweater + navy trousers + loafers

A white long-sleeve button-up shirt with a collar, displaying a minimalist design.
A young woman standing in front of a plain light background, wearing a dark navy sweater and faded blue jeans, with her hair down and a neutral expression.
Model wearing a navy blue sweater with a white collar and matching navy trousers, holding a small black handbag.
Burgundy leather loafers featuring a stitched detailing and a low heel.

Or:

Cream cardigan + dark denim + leather loafers

A woman wearing a beige cardigan over a white shirt, paired with black wide-leg pants and black pointed-toe shoes, stands against a plain background. She has long dark hair and is wearing sunglasses.
A pair of dark blue wide-leg denim jeans displayed against a plain background.
A pair of elegant brown leather slip-on shoes, featuring a smooth surface and minimalistic design.

When your outfit is this simple, quality and fit become especially important.

If Your Style Is Bohemian

Prep can give a bohemian wardrobe a little more structure.

Pair your flowy dresses and embroidered blouses with tailored blazers, loafers, riding boots, or classic cardigans.

The contrast between relaxed and structured pieces keeps the outfit from feeling too precious.

Try:
Flowy floral dress + oversized blazer + loafers

A woman wearing a floral maxi dress with a ruffled neckline, belted at the waist, standing in brown leather boots.
A model wearing an oversized black blazer over a white t-shirt, paired with high-waisted blue jeans, posing against a neutral-colored wall.
A pair of elegant black leather loafers featuring a gold buckle detail.

Or:

Embroidered blouse + straight-leg jeans + riding boots

A woman with long dark hair wearing a white blouse with intricate detailing and blue flared jeans, sitting in a relaxed pose with a gold necklace.
A person wearing high-waisted dark blue jeans, a blue and white striped shirt, and brown loafers, standing against a neutral background.
A pair of tall brown leather boots with a low heel and a sleek design.

This is especially good if your bohemian style has started feeling a little too loose or unstructured.

If Your Style Is Edgy

This is where preppy style gets really interesting.

Instead of softening your wardrobe with prep, let the prep pieces become the unexpected element.

Wear a traditional blazer with leather pants. Pair a pleated skirt with chunky boots or loafers. Wear a rugby shirt with dark denim and a leather jacket.

Try:
Plaid blazer + fitted tee + leather pants + ankle boots

A woman sitting on a chair wearing a stylish plaid blazer over a white top and denim jeans, set against a beige backdrop.
A young woman with long dark hair wearing a plain white t-shirt and black leggings, standing against a light background.
A model wearing high-waisted black faux leather pants paired with pointed toe black heels and holding a small black handbag.
A pair of stylish black leather ankle boots with a pointed toe and a low heel.

Or:

Pleated mini skirt + oversized rugby shirt + leather jacket + chunky boots or loafers

A model wearing a gray pleated skirt, paired with black flats, showcasing a casual yet stylish look.
A young woman standing against a plain background, wearing a gray long-sleeve shirt with red and white stripes, a white collared shirt underneath, and a plaid skirt. She is also wearing gray socks and black shoes.
A woman wearing a black leather jacket over a white shirt, standing against a white background.
Black patent leather loafers with a chunky sole and decorative buckle detail on the side.

If Your Style Is Sporty

You already have a head start.

Collegiate style and sporty style naturally overlap, especially this season.

Try varsity jackets, rugby shirts, polos, sweatshirts, baseball caps, sneakers, and athletic-inspired pieces—but balance them with something more polished.

Try:
Rugby shirt + straight-leg jeans + loafers

A woman standing against a light wall, wearing a striped long-sleeve shirt in brown, white, and light blue, paired with light blue jeans.
A model wearing a white t-shirt and high-waisted blue jeans, standing confidently against a neutral background.
A pair of brown loafers with a textured fabric upper and a simple design, labeled with 'ROTHY'S' on the insoles.

Or:

Varsity jacket + simple knit dress + sneakers

A woman with curly hair wearing a navy blue varsity jacket with white stripes on the cuffs, standing confidently with her hands together.
A woman wearing a sleeveless navy ribbed midi dress, standing with one hand on her hip and the other relaxed at her side, against a light gray background.
A pair of white and navy athletic sneakers with gum soles, featuring laces and a minimalist design.

The secret is mixing athletic and tailored pieces rather than wearing an entire sporty outfit.

If Your Style Is Trendy or Fashion-Forward

Don’t recreate prep exactly as it appeared in the 1980s or 1990s.

Instead, take one recognizable preppy element and style it in an unexpected way.

Try an oversized rugby shirt with a sleek skirt. Wear an argyle sweater with wide-leg trousers. Pair a traditional blazer with an ultra-feminine top. Play with proportions.

Try:
Oversized cable-knit sweater + silky midi skirt + loafers

A model wearing a cream-colored cable knit sweater paired with black pants, standing against a light gray background.
A model sitting on a wooden chair, wearing a light beige sleeveless top and a dark brown skirt with lace detailing, displaying a thoughtful expression.
A pair of dark brown leather loafers featuring a classic design with decorative stitching and a small emblem on the front.

Or:

Cardigan + wide-leg trousers + pointed shoes

A model wearing a beige argyle cardigan and brown suede shorts, posing in front of a wooden background.
A person wearing wide-leg dark trousers paired with a striped long-sleeve top and flat sandals.
Pair of burgundy Tory Burch slingback high-heeled shoes with pointed toes and a strap across the instep.

The more modern the silhouette, the less likely your outfit is to feel like a costume.

If Your Style Is Parisian or French-Inspired

There is already plenty of overlap here: Breton stripes, loafers, cardigans, tailored trousers, ballet flats, blazers, and button-down shirts all work beautifully with a French wardrobe.

The easiest way to combine the aesthetics is to keep the prep slightly undone.

Think a striped marinière with relaxed jeans, a cardigan buttoned as a top, or a blazer worn with a simple tee and ballet flats.

Try:
Breton stripe + straight-leg jeans + loafers + structured handbag

A model wearing a striped long-sleeve top with white cuffs, paired with brown wide-leg pants, holding a brown handbag against a neutral background.
A pair of blue high-waisted denim jeans displayed against a light background.
A pair of brown suede loafers displayed on a neutral background.
A stylish red leather handbag with a structured design, featuring dual handles and a detachable shoulder strap.

Or:

Navy cardigan + silk skirt + ballet flats + delicate jewelry

A woman wearing a navy blue cardigan, standing with her hands in her pockets, paired with dark denim pants.
A fashionable woman wearing a white tank top and a beige satin midi skirt, standing against a neutral background.
Top view of a ballet flat shoe featuring a black cap toe and a tan body, with a decorative bow detail on the front.
Close-up of a person's neck wearing two delicate gold necklaces with heart-shaped pendants, paired with a cozy cream-colored cardigan.

Keep the palette elegant and let one slightly unexpected detail make the outfit feel like you.

If Your Style Is Glamorous

Prep doesn’t have to mean casual.

Use classic pieces as a backdrop for more luxurious or feminine accessories.

A cashmere sweater looks gorgeous with a satin skirt. A classic blazer can be paired with statement earrings. A simple polo becomes much more sophisticated with a beautiful handbag and polished shoes.

Try:
Cashmere crewneck + satin midi skirt + knee high boots + statement earrings

A smiling woman with long blonde hair, wearing a brown sweater and a maroon belt, posing for the camera.
A model wearing a burgundy satin midi skirt paired with black high-heeled boots.
A stylish knee-high burgundy leather boot with a chunky heel and a decorative buckle.
A pair of elegant gold-tone earrings with a twisted design, featuring rounded shapes and a shiny finish.

Or:

Fitted polo + wide-leg trousers + heels + structured handbag

A model wearing a fitted brown long-sleeve polo top and wide-leg brown trousers, holding a dark handbag.
A woman standing confidently, wearing an off-white sweater and brown high-waisted trousers with a belt, posing against a plain background.
Brown leather slingback high heel shoe with a pointed toe and a slender heel.
A stylish burgundy leather handbag with a long strap and a buckle detail, displayed against a soft neutral background.

Think country club meets cocktail hour.

Don’t Forget Accessories

Sometimes the easiest way to add prep is through accessories.

Loafers. A leather belt. Pearl earrings. A structured handbag. A silk scarf. A classic watch. Tortoiseshell sunglasses. A baseball cap. A monogrammed tote.

You can wear an otherwise very modern outfit and make it feel subtly preppy simply by adding one of these details.

And this is really useful if you’re experimenting with the trend rather than trying to invest in an entirely new wardrobe.

Choose the pieces you genuinely love.

The goal is to let a little prep expand your personal style.

And that’s really the chicest way to approach any trend: take what works, leave what doesn’t, and make it your own.

Xo, Courtney

courtneyimade
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One response to “The Chic Guide to Mixing Preppy Style With Your Personal Style”

  1. Avatar
    Anonymous

    Love these looks especially burgundy handbag! I hadn’t heard of Oleada, so I’m checking them out – it frustrates me to no end when I see a tote that has no pockets and is open at the top! I alos have argyle and plaid on my wishlist for fall outfits. Xo Nipa

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