Have you ever found yourself in front of your wardrobe, unsure whether to channel the crisp, youthful vibe of preppy style or embrace the understated elegance of old money fashion? It’s a common conundrum, especially when both styles radiate class and sophistication, albeit in different ways. Understanding what distinguishes these two styles can not only help you refine your fashion sense but also ensure you project the image you want.
What Defines Preppy Style?
Preppy style finds its roots in the elite preparatory schools of the Northeastern United States. It’s characterized by a clean, polished, and youthful appearance with a touch of academia and sports influence. This look often represents a lifestyle associated with affluence but isn’t overtly luxurious or flamboyant.

Key Features of Preppy Style
- Color Palette: Think nautical; blues, whites, reds, and sometimes a touch of yellow or green. Pastels are also common.
- Patterns: Preppy style incorporates stripes, checks, plaids, and argyle patterns. These add a playful yet classic element to the attire.
- Fabrics: Cotton, wool, and linen dominate, given their comfort and durability. In preppy fashion, materials are important to the overall aesthetic.
- Signature Pieces: Polo shirts, khakis, cardigans, loafers, and blazers are staples. Expect to see items like V-neck sweaters and rugby shirts as well.
- Accessories: Ties (often featuring fun colors or motifs), boat shoes, watches with colorful bands, and belts with distinctive prints or emblems.
Outfit Inspiration: Preppy Style
- Casual Day Out:
- Light blue polo shirt
- Cream-colored chinos
- Brown loafers
- A sporty watch with a striped band
- Smart Casual Event:
- Navy blazer
- Patterned pocket square
- White dress shirt
- Grey trousers
- Tassel loafers
- Weekend Look:
- Striped t-shirt
- Khaki shorts
- White sneakers
- A canvas belt with a fun pattern
The Essence of Old Money Style
Old Money style exudes an aura of understated elegance. Unlike preppy style, it is not tied to a specific age group or demographic, but rather a way of dressing that signifies generational wealth without artifice. It is timeless, heavily relying on quality craftsmanship and classic silhouettes.

Key Features of Old Money Style
- Color Palette: Stick to earth tones, muted colors, and classic monochromes. Think navy, black, grey, cream, and the occasional deep green or burgundy.
- Patterns: Subtle patterns like pinstripes or houndstooth are favored. These designs are often less noticeable but contribute to the ensemble’s sophistication.
- Fabrics: High-quality materials like cashmere, silk, and high-grade wool are essential. The fabric quality often assures longevity, a true hallmark of old money fashion.
- Signature Pieces: Tailored suits, trench coats, vintage watches, high-quality leather shoes, and button-down shirts.
- Accessories: Discreet yet luxurious, such as a leather strap watch, gold cufflinks, or subtle tie patterns.
Outfit Inspiration: Old Money Style
- Office Attire:
- Dark charcoal suit
- Crisp white shirt
- Silk tie in a subtle pattern
- Black oxford shoes
- Formal Gathering:
- Midnight blue tuxedo
- White dress shirt with French cuffs
- Black patent leather shoes
- Vintage cufflinks
- Relaxed Luxury:
- Cashmere sweater in camel
- Pleated wool trousers
- Leather loafers
- Classic leather belt

Comparing Preppy and Old Money Styles
To better understand these styles, let’s compare them directly:
Feature | Preppy Style | Old Money Style |
---|---|---|
Color Palette | Brighter, nautical hues, and pastels | Earth tones and muted colors |
Patterns | Bold with argyles, stripes, and emblematic prints | Subtle, understated patterns like pinstripes |
Fabric | Comfortable and practical cotton, wool, and linen | Luxurious materials such as silk, cashmere, and high-grade wool |
Signature Pieces | Polo shirts, khakis, loafers | Tailored suits, trench coats, vintage watches |
Accessories | Colorful ties, boat shoes | Discreet luxury, e.g., gold cufflinks, leather strap watches |
How to Choose the Right Style for You
Consider your lifestyle and personal preferences. If your environment is more laid-back and youthful, or if you’re drawn to sporty, playful looks with a touch of academia, preppy might be your way to go. On the other hand, if you prefer timeless elegance with an emphasis on quality and sophistication, old money style could be your perfect fit.
Mixing and Matching
It’s entirely possible to mix both styles to create a unique look that reflects your personal taste. For instance, pair a preppy striped sweater with high-quality old money trousers for a balanced outfit.

Navigating the Fashion Landscape
In fashion, understanding various styles ensures versatility and confidence in your choices. Whether you lean more towards preppy or embody the old money aesthetic, both styles offer timeless appeal and can be tailored to fit any occasion. What truly matters is how you feel in what you wear. Confidence, after all, is the key component of any great style.
Final Thoughts
Both preppy and old money styles have their roots steeped in tradition, yet each offers a unique expression of classic fashion. Whether you’re donning a pastel sweater over a collared shirt or slipping into a tailored suit with heritage charm, you’re partaking in a sartorial history that continues to evolve. Embrace what resonates with you, and make it your own, because the best style is one that aligns with your identity and lifestyle.