1. Leather Loafers
Loafers are the perfect blend of polish and comfort. A well-crafted leather loafer oozes a relaxed yet sophisticated air. It looks beautiful when paired with fitted trousers, crisp white blouses, or even linen tops. No matter if you choose sleek black, rich brown, or soft camel shade, loafers provide structure and elegance to your appearance without doing much.
They're generally popular among women who value functionality and timeless fashion. They can be walked in throughout the city, visited for an art museum, or driven between weekend homes. Choose timeless penny or horse-bit shapes with minimal ornamentation for the most traditional look.
2. Low-Heeled Slingbacks
Slingbacks are subtle elegance. With the thin strap placed across the back of the ankle and a modest heel, they draw up a classy figure without shouting it out loud. Old money style is not about skyscraper heels; it's about dressing up well and walking easily.
Slingbacks are excellent over midi skirts, cashmere cardigans, or a blazer and dress pants. Choose pairs in smooth leather, patent, or suede. Ivory, beige, or navy colors add sophistication to their appearance.
3. Riding Boots
Nothing says country-chic like a pair of knee-high leather riding boots. They were first invented to ride horses, but these boots have been wardrobe staples for the upper class for decades. They're hardy, reliable, and long-lasting for decades, which perfectly aligns with old money's focus on quantity rather than quality.
Wear them with wool pants, a turtleneck, or a trench coat during the fall and winter. If you're country-bound or love classic British fashion, these boots are an essential in your wardrobe. The best ones have clean lines, minimal hardware, and are constructed in thick, matte leather.

4. Ballet Flats
Ballet flats are a classic of subtle elegance. Borrowed from actual dance shoes, they bring a soft, feminine touch to almost any outfit. Old money women wear plain variations - no bows, logos, or gaudy patterns. Just tidy, well-made shoes that mold to the foot.
They work perfectly with ankle-length trousers, shift dresses, or even denim with a silk blouse. The key is to choose high-quality materials like lambskin, suede, or even soft canvas with leather lining. You’ll often see these shoes in muted colors like cream, black, or dusty rose.

5. Classic Espadrilles
For warm weather, espadrilles are the classic old money summer staple. They're casual comfort without looking too sloppy. Woven-solied espadrilles with linen or cotton uppers are perfect for seaside vacations, garden parties, or a strolling city afternoon.
Choose ones with a simple slip-on or easy ankle tie. They go well with linen pants, shirt dresses, or flowy skirts. While others play with bold prints, the old money type is always understated - whites, beiges, and washed-out blues.

Final Thoughts
Old money style isn't about showing off - it's about investing in pieces that get better with time and make you look put together. All of these five types of shoes are about refinement, comfort, and heritage. They don't scream "look at me," but rather whisper softly, "I belong."
So, whether you’re building your wardrobe from scratch or looking to upgrade a few pieces, start from the ground up - with shoes that will never go out of style.