There’s a unique kind of elegance that comes with “old money” style—a quiet confidence rooted in generational wealth, understated luxury, and timeless fashion. In a world flooded with loud logos and passing trends, old money fashion is the calm in the storm. It’s not about flaunting wealth but about curating a polished, refined look that speaks volumes through its subtlety.
And yes, this effortless style doesn’t just belong to adults. Whether it’s for a school function, family gathering, vacation, or a formal event, boys can absolutely embody the old money aesthetic with the right wardrobe pieces.
In this guide, we’ll show you 11 old money outfits for boys—each designed to reflect timeless sophistication without overdoing it. From crisp button-downs to linen shorts, we’re diving into the essential pieces and outfit formulas that define the legacy of classic prep.
What Is “Old Money” Fashion, Exactly?
Before we jump into the looks, let’s define the term. Old money refers to wealth passed down through generations, often associated with established families who maintain traditional values and understated elegance. The fashion that comes with this culture is:
- Timeless over trendy
- Quality over quantity
- Neutral tones over bold colors
- Tailored fits over baggy silhouettes
- Luxury fabrics like wool, cotton, and linen
So now that we’ve laid the foundation, let’s explore 11 curated old money outfits boys can wear to channel charm, confidence, and class.
1. The Classic Polo + Chino Combo
Perfect for: Casual gatherings, brunches, and country clubs
A white or pastel-colored polo shirt paired with tan or khaki chinos is the unofficial uniform of prep school royalty. Choose breathable cotton fabrics and make sure the shirt fits snugly at the shoulders—not too loose, not too tight.
Add-ons:
- Leather loafers or boat shoes
- Woven belt
- Minimalist watch
2. Cable Knit Sweater Over Collared Shirt
Perfect for: School photos, family dinners, cooler weather
Layer a navy, cream, or burgundy cable knit sweater over a white oxford shirt. Let the collar and cuffs peek out for contrast. This is a textbook old money layering look.
Pro tip: Add a herringbone scarf or a structured wool coat for added flair.
3. Seersucker Blazer with Linen Pants
Perfect for: Summer weddings, church events, coastal trips
Seersucker is an old-money staple, especially in the warmer months. A pale blue seersucker blazer paired with white linen trousers offers a coastal, preppy elegance that’s perfect for formal settings without the discomfort.
Shoes to match: White loafers, brown leather sandals
4. Double-Breasted Navy Blazer + Crisp Dress Shirt
Perfect for: Holiday parties, award ceremonies
A double-breasted blazer in navy with gold or horn buttons is straight from the playbook of prep school traditions. Pair with a well-pressed white dress shirt, gray trousers, and a silk tie.
Optional: Add a crest on the blazer pocket for that Ivy League effect.
5. Sweater Vest + Button-Up + Trousers
Perfect for: Autumn outings, old libraries, or museum trips
A fitted knit sweater vest (think Argyle or solid cashmere) over a checkered or striped button-down shirt and wool trousers is both warm and stylish. It brings a scholarly, vintage vibe reminiscent of 1950s boarding schools.
Color palette tip: Stick to browns, navy, forest green, and cream.
6. Linen Short-Sleeve Shirt + Tailored Shorts
Perfect for: Yacht days, garden parties, tropical vacations
Old money doesn’t shy away from comfort—but never at the cost of elegance. A white or light blue linen shirt with tailored beige or navy shorts offers breathable sophistication. Choose mid-thigh length shorts for a clean silhouette.
Accessories: Panama hat, slip-on loafers, leather strap sandals
7. Turtleneck + Wool Trousers
Perfect for: Winter events, book readings, gallery visits
A soft, fitted turtleneck in cream, gray, or camel color paired with pleated wool trousers is minimalist yet expressive. This is a look that whispers refinement and maturity.
Pro tip: Add a long coat and leather gloves when it’s extra cold.
8. Oxford Shirt + Sweater Draped Over Shoulders
Perfect for: Country club events, family vacations
Nothing says “prep” like a pastel or white Oxford shirt with a cashmere sweater loosely draped and tied around the shoulders. It’s casual chic, effortlessly blending ease with elegance.
Style note: Add chino shorts and leather moccasins for a full Hamptons-inspired look.
9. Houndstooth Blazer + Turtleneck + Corduroys
Perfect for: Holiday photoshoots, winter weddings, upscale events
A bold yet traditional outfit—houndstooth print adds vintage character. Layer a turtleneck underneath for a modern twist and choose rich-toned corduroy trousers (think olive, rust, or navy) for texture and depth.
Finish it with: Chelsea boots or polished oxfords
10. Trench Coat + Cashmere Scarf + Slacks
Perfect for: Rainy-day strolls, European travels
This is pure old money charm. A camel or stone-colored trench coat layered over a fine wool suit or just a shirt-and-slacks combo delivers cinematic elegance. Wrap a cashmere scarf around the neck for both function and form.
Shoes to wear: Suede chukkas, leather boots, or brogues
11. The Boarding School Uniform Look
Perfect for: Fall fashion shoots, back-to-school seasons
This ensemble includes a navy blazer, light blue Oxford shirt, gray wool pants, and knee-high socks (if formal enough). It’s a timeless uniform rooted in tradition, with an elite academic flair.
Pro tip: Keep the look authentic with black loafers and a leather satchel bag.
Bonus Tips: Styling Old Money Outfits for Boys
Want to take these outfits to the next level? Here are a few extra pointers:
- Prioritize tailoring: Clothes should fit—not hang loose or constrict movement.
- Neutral color palettes: Stick to beige, navy, cream, gray, and earthy greens.
- Use subtle accessories: Leather belts, classic watches, and sunglasses elevate the look.
- Avoid loud logos: Brand loyalty is irrelevant; quality fabric and timeless design win.
- Layer wisely: Always choose natural fibers like cotton, wool, or linen when layering.
Where to Shop Old Money Outfits for Boys
Here are some brands and stores that consistently offer pieces matching the old money vibe:
- Ralph Lauren: Polo shirts, trousers, and formalwear
- Brooks Brothers: Button-ups, blazers, and knitwear
- Janie and Jack: Premium boys’ collections
- H&M Premium / Zara Kids: Budget-friendly dupes with clean tailoring
- Petit Bateau / Jacadi: French classics with timeless appeal
Final Thoughts
Old money fashion isn’t just about looking rich—it’s about honoring a tradition of refinement, minimalism, and smart dressing. These 11 old money outfits for boys prove that age doesn’t matter when it comes to cultivating a classic sense of style. With a few well-chosen pieces and a little attention to detail, any boy can step into timeless elegance.
So, whether you’re dressing your son, nephew, or younger brother, these outfits promise confidence, charm, and character—without ever needing to shout.