The Best Shoes for The Prep Look: Loafers & Boots Every Chic Woman Needs

Fall fashion has always had a love affair with prep. From cable knits and equestrian silhouettes, the prep look is equal parts classic and cheeky. But here's the secret- the right shoes are what transform "back to school" polish to grown-up city chic.

At Luna Selene, we've reimagined prep essentials- handcrafted in Italy, designed for the modern women who love heritage style with a glossy twist. Think croc-embossed loafers, equestrian-inspired boots that carry you seamlessly from weekday meetings to weekend escapes.

Fall preppy outfit with loafers and a tailored blazer

(Photo: Pinterest)

Why Prep Style Never Goes Out of Fashion

The prep aesthetic has been a style staple for decades because it's timeless, versatile, and easy to elevate. Preppy shoes - especially loafers and tall boots- add polish to denim, ground a sharp blazer, or soften a feminine dress. They're the ultimate fall transition pieces.

Whether you're channeling a Town & Country weekend or your inner Gossip Girl, prep footwear is the fastest way to make your wardrobe look intentional, elevated, and a bit cheeky.

The Loafer: A Prep Classic, Reimagined

A glossy black loafer is the crown jewel of prep style shoes. But today’s version isn’t stuck in the past—it’s bold, modern, and made to shine.

Patent perfection: Croc-embossed leather brings depth and texture that feels luxe.
Everyday versatility: Wear them with denim, trousers, or even a silk slip dress for that effortless “borrowed from the boys” energy.
Quiet luxury appeal: They whisper tradition but announce confidence.

This isn’t just a schoolgirl staple—it’s the shoe that defines fall 2025 prep fashion.

The Equestrian Boot: Fall’s Chicest Staple

Tall equestrian boot with chic fall outfit

If the loafer is prep’s heart, the equestrian boot is its stride. Sleek, sculpted, and unapologetically timeless, these tall boots are built for crisp autumn mornings and city nights alike.

Equestrian spirit: Inspired by countryside rides, perfected for metropolitan life.
Wardrobe transformer: Pairs effortlessly with wool skirts, oversized knits, and tailored coats.
Confidence in leather: A boot that’s practical, powerful, and undeniably chic.

Equestrian boots are more than footwear—they’re a fall ritual, and the most stylish women know they anchor the entire look.

How to Style Shoes for the Prep Look in 2025

With denim: A glossy loafer + straight-leg jeans = preppy cool without trying too hard.
With tailoring: Tall boots + a herringbone blazer = polished power.
With dresses: Pair equestrian boots with a midi dress to soften prep with femininity.
With layers: Loafers peeking out under cropped trousers give prep its wink.

Preppy fall outfit with equestrian boots and jeans.

Prep, but Make It Chic

The best shoes for the prep look this season are classics elevated: a polished loafer with a modern edge and a tall equestrian boot with timeless appeal. Both are handmade in Italy by Luna Selene, designed to carry you through fall with elegance, wit, and a stride that’s all your own.

Step into prep the chic way—because this season, tradition has never looked so modern.

Discover the Luna Selene Grace Loafer and The Novak Boot.

Nailing the Prep Look FAQs

What are the best shoes for the prep look?

The best shoes for the prep look are classic loafers and tall equestrian boots. Loafers add polish and shine to everyday outfits, while equestrian boots bring timeless sophistication to fall style. Both are staples that make any preppy wardrobe feel chic and modern.

Are loafers still in style for women in 2025?

Yes! Women’s loafers are not only still in style for 2025, they’re one of the biggest fall fashion trends. Glossy, croc-embossed loafers elevate the classic prep aesthetic while offering comfort and versatility for city life.

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How do you style equestrian boots in fall?

Equestrian boots are perfect for fall layering. Pair them with tailored trousers and blazers for a sharp prep look, or with a midi dress and oversized knit for countryside chic. They’re versatile enough to move from the office to the weekend effortlessly.

What makes Luna Selene shoes unique?

Luna Selene shoes are handcrafted in Italy with timeless silhouettes, premium leathers, and cushioned insoles. Each pair blends heritage style with modern edge, giving the prep look a luxurious update designed for today’s woman.

Shannon Slack dreamed of building a small luxury brand that was defined by a woman’s wish to reimagine her feminine style.

With the modern fashion industry focused on dressing down, she wanted to create a brand for women who cherished the art of dressing up.

A fierce lover of mid-twentieth-century fashion, her designs are classically inspired, feminine, and comfortable.

Red, the color of power, is the mainstay throughout many of her designs, while the block heel is incorporated to ensure Luna Selene shoes can be worn from “desk to dusk.”

Her vision has evolved since Luna Selene launched in the Fall of 2020, and she continues to create designs that are inspired and influenced by the women she meets every day.

The Jackie O. Houndstooth Bootie is a fashionable and timeless shoe, featuring a chic black and white houndstooth pattern. The intricate fusion of the houndstooth textile upper and the Venetian red heel creates a "classically cool" aesthetic.

This ankle bootie is perfect for channeling your inner Emily In Paris. It comes with a modern, 2-inch red patent block heel that is comfortable to wear all day long.

The luxurious gel, leather insole will mold to your feet, while the outsole with rubber grip provides maximum stability.

This unique shoe is perfect for any holiday party, and it's unlikely that anyone else will be wearing it (unless they have great taste and have already bought it, wink). You can wear it to coffee, dinner, drinks, nights out with the girls, holiday parties, and more!

Redefine Romance with the Timeless Beauty of the Monroe Red Pump - A Sublime Gesture Beyond Roses and Letters.

Indulge me for a moment, dear. Picture this: the perfect way to express your love for someone special. What comes to mind? Is it a bouquet of red roses or a sweet love letter?

Well, let me tell you, my dear, the Monroe Red Pump is a fan-favorite that will put all your conventional ideas to shame.

Crafted with premium Italian leather, this pump boasts a show-stopping, sunset-red, suede leather upper that will add color to your Valentine's outfit. And the best part? The gel insole ensures you won’t curse your shoes halfway through the night.

The Monroe Red Pump exudes elegance and sophistication, with its pointed toe that elongates the foot, illuminating a feminine silhouette. And let's not forget about the comfortable 3.1-inch block heel that will have you strutting your stuff like a true boss.

Now, let me give you a little insider tip, my dear. This hot, red pump is not just for Valentine's Day.

Oh no, no, no. It's perfect for any occasion that requires a killer outfit. From date nights to weddings and even the office, the Monroe Red Pump will set any room on fire.

So go ahead, my dear, channel your inner Marilyn and let the Monroe Red Pump do the talking. Follow our size conversions unless you want to hobble around like a baby deer.

Embrace Sophistication and Luxury with our Handcrafted Italian Shoes.

The Finer Details:
Made with premium Italian Leather and hand-crafted with care.
Produced in small batches by master shoemakers. Handcrafted in Italy.

How To Wear:
Dress up a "casual work day" by pairing these loafers with your favorite jeans and blazer. Add to a cute spring dress or white jeans for a soft, feminine vibe.

Where To Wear:
Best for Saturday afternoon, museum-hopping, cherry blossom strolls, and long lunches. Best for: Saturday afternoon, museum-hopping, cherry blossom strolls, and long lunches. This shoe will also act as a major staple in your workwear attire!

BELOVED CLIENTELE / FRIENDS & FAMILY

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