Fashion trends may come and go, but certain styles remain timeless. Among these enduring styles are Old Money outfits and Preppy styles. While they share classic roots, these styles are distinct in their aesthetic and appeal. In this article from Men to Gentlemen, we’ll dive deep into the differences between old money vs. preppy style, helping you understand how to adopt each look effortlessly.
Contents
- 1 Introduction: Understanding the Aesthetic
- 2 A Quick Look at the History of Old Money and Preppy Style
- 3 Key Elements of Old Money Fashion
- 4 Luxury Brands for Old Money Fashion
- 5 Understanding Preppy Fashion Style
- 6 Old Money vs. Preppy style: What’s the Difference?
- 7 How to Dress Like Old Money vs. Preppy Fashion for Men
- 8 Can You Mix Old Money and Preppy Styles?
- 9 FAQs
- 10 Conclusion:
Introduction: Understanding the Aesthetic
Fashion is often influenced by tradition, and both Old Money and Preppy fashion styles are examples of timeless menswear. These styles have endured the test of time because they are associated with class, elegance, and sophistication. Yet they express these qualities differently:
- Old Money fashion focuses on understated luxury and elegance.
Preppy fashion is youthful, vibrant, and tied to Ivy League collegiate culture.
So, what’s the difference between these two iconic styles? Let’s explore.
A Quick Look at the History of Old Money and Preppy Style
Old Money Outfits: The Roots of Timeless Elegance

The Old Money aesthetic is inspired by European aristocracy, where fashion was less about trends and more about timeless investment pieces. This style emphasizes:
- Tailored suits in classic colors like navy, grey, and black.
- Luxurious fabrics like cashmere, tweed, and fine wool.
- Quality leather accessories like Oxford shoes, belts, and bags.
Old Money outfits are all about refined simplicity—nothing too flashy, just pure elegance that speaks of generational wealth and sophistication.
Preppy Fashion Style: Youthful and Playful

In contrast, Preppy fashion style emerged from the Ivy League universities of the United States in the early 20th century. This style was inspired by elite sports like rowing, golf, and tennis. Preppy fashion is:
- Bright and colorful, with pastel hues and vibrant patterns.
- Casual yet polished, focusing on comfort without sacrificing style.
- Classic pieces like polo shirts, chinos, boat shoes, and lightweight sweaters.
The preppy look is all about a well-groomed, approachable style with a youthful twist.
Key Elements of Old Money Fashion
Outfits for Building a Timeless Wardrobe
To dress in this fashion, consider investing in these timeless fashion mens pieces:
- Tailored Suits: Opt for classic fits in neutral tones like navy and grey.
- Tweed Blazers and Cashmere Sweaters: These add a touch of sophistication and are perfect for layering.
- Leather Accessories: A good leather belt, classic dress shoes, and a timeless watch are essentials.
- Muted Color Palette: Stick to earthy tones like olive, beige, and deep blues to keep the look understated.
Luxury Brands for Old Money Fashion

If you’re aiming to embody the Old Money aesthetic, these brands are known for their timeless pieces:
- Ralph Lauren: For its classic American elegance.
- Brooks Brothers: The epitome of sophisticated tailoring.
- Burberry: Renowned for its British charm and iconic trench coats.
Understanding Preppy Fashion Style
Outfit Essentials
Preppy fashion is all about being effortlessly stylish and comfortable. Key items for a preppy wardrobe include:
- Polo Shirts and Button-Downs: These are versatile and can be dressed up or down.
- Chinos and Khakis: Lightweight and comfortable, perfect for a polished yet relaxed look.
- Boat Shoes and Loafers: These shoes are stylish yet comfortable, ideal for casual outings.
- Pastel Colors and Stripes: Embrace patterns like nautical stripes and colors like sky blue, pink, and yellow for a vibrant look.
Popular Preppy Brands

To achieve the perfect preppy look, check out these well-known brands:
- J. Crew: Known for its timeless essentials and classic fits.
- Vineyard Vines: Offers a fun, laid-back take on the preppy style.
- Lacoste: Iconic for its colorful polo shirts and casual elegance.
Old Money vs. Preppy style: What’s the Difference?
Differences in Style, Materials, and Colors
- Old Money outfits use luxurious, durable fabrics like cashmere and wool. The colors are muted and sophisticated.
- Preppy fashion style uses lighter materials like cotton and focuses on bright, playful colors.
Styling Approach
- Old Money is about timeless sophistication—nothing too loud, just quietly elegant.
- Preppy fashion leans into fun patterns, bold colors, and a laid-back but put-together vibe.
How to Dress Like Old Money vs. Preppy Fashion for Men
Old Money Outfit Ideas

- Formal Look: A navy tailored suit paired with a crisp white shirt and polished leather shoes.
- Casual Look: A cashmere sweater, wool trousers, and loafers.
Preppy Style Outfit Ideas

- Classic Preppy Look: A pastel polo shirt, chinos, and boat shoes for a casual yet stylish vibe.
- Weekend Casual: A striped sweater, cuffed jeans, and white sneakers for a relaxed but polished look.
Can You Mix Old Money and Preppy Styles?

Yes, it’s possible to blend these two aesthetics to create a unique, sophisticated look. For example:
- Pair a tweed blazer with a pastel preppy shirt.
- Mix tailored trousers with colorful accessories for a refined yet youthful style.
- Use classic leather pieces alongside playful preppy elements to achieve a balanced look.
FAQs
Which Style is More Formal?
Old Money outfits are better for formal occasions due to their focus on tailored and sophisticated pieces. Preppy fashion is great for casual or semi-formal settings.
Can I Mix Old Money and Preppy Fashion Styles?
Absolutely! Combining classic pieces like blazers with colorful preppy items can create a balanced and stylish outfit.
What Are Affordable Ways to Dress in Old Money or Preppy Styles?
Thrift stores and second-hand shops are great places to find quality pieces. Also, watch for sales from brands like J. Crew and Ralph Lauren.
How Can I Achieve the Old Money Look on a Budget?
Focus on classic basics like blazers, leather accessories, and well-fitted trousers. Stick to neutral colors for timeless appeal.
What Are the Best Brands for Old Money Outfits?
Brands like Ralph Lauren, Burberry, and Brooks Brothers offer timeless pieces that fit the aesthetic.
Conclusion:
Choosing Between Old Money and Preppy Fashion
Whether you’re drawn to the quiet elegance of Old Money outfits or the vibrant charm of Preppy fashion, both styles have something unique to offer. The key is to find what aligns best with your personality and lifestyle. Explore these styles and create a wardrobe that is not just fashionable but timeless.
1 Comment
This was a good summary.