Old money style is more than clothing. It reflects quiet confidence, tradition, and understated class. Unlike flashy trends, old money outfits show elegance without shouting for attention. Think of navy blazers, tailored trousers, leather loafers, and neutral tones.
This guide covers 25 old money outfits for men. Each one includes key pieces, styling tips, and ideas for when to wear it. The goal is to help you build a wardrobe that lasts, with timeless outfits that always look polished.
Each outfit below blends comfort, polish, and timeless design.
1. Classic Ivy League Look
The Ivy League look is the foundation of old money style.
Key pieces: Navy blazer, white Oxford shirt, khaki chinos, brown loafers.
How to style it: Keep the shirt crisp and tucked. Add a silk pocket square for detail. Finish with a slim leather belt and clean haircut.
When to wear: Perfect for casual business settings, campus events, or semi-formal dinners.
2. Weekend Country Club Attire
This is relaxed yet smart, a look seen often at golf clubs.
Key pieces: Cream polo shirt, beige pleated trousers, suede loafers, leather watch.
How to style it: Keep trousers pressed. Avoid sneakers. Add dark sunglasses for polish.
When to wear: Ideal for weekend brunches or afternoons at the club.
3. Fall Campus Outfit
Layers define this outfit. It works best in cool weather.
Key pieces: Cable-knit sweater, collared shirt, wool trousers, brown brogues, scarf.
How to style it: Let the shirt collar peek above the sweater. Keep colors muted. Add a leather satchel for heritage appeal.
When to wear: Works well for campus strolls, library study, or city walks.
4. Summer Sailing Outfit
The sailing look is light and breezy.
Key pieces: Striped linen shirt, white shorts, boat shoes, woven belt.
How to style it: Keep shirt sleeves rolled. Shoes should match the belt. Sunglasses add sharpness.
When to wear: Best for boat trips, seaside lunches, or resort stays.
5. Winter Coat Elegance
Outerwear is the star here.
Key pieces: Camel overcoat, cashmere turtleneck, navy wool trousers, Chelsea boots.
How to style it: Wear the coat open to show the turtleneck. Add gloves and a leather briefcase.
When to wear: Suited for city winters, evening dinners, or business travel.
6. Preppy Tennis Look
Tennis has shaped old money style for decades.
Key pieces: White polo sweater, shorts, white sneakers, vintage racket.
How to style it: Keep everything clean and pressed. Add striped details for tradition.
When to wear: Sports settings, summer gatherings, or casual leisure events.
7. Oxford Gentleman Style
This outfit balances academic charm and refined tailoring.
Key pieces: Grey houndstooth blazer, light blue shirt, navy tie, beige chinos.
How to style it: Stick with matte fabrics. Keep tie knot small and neat.
When to wear: Perfect for lectures, meetings, or formal dinners.
8. Rugged Countryside Look
Country life inspires earthy tones and textured fabrics.
Key pieces: Tweed jacket, plaid shirt, corduroy trousers, leather boots, flat cap.
How to style it: Add layers for warmth. Keep patterns subtle.
When to wear: Best for estate visits, hunting events, or rural weekends.
9. Formal Dinner Outfit
Black tie events call for timeless pieces.
Key pieces: Black tuxedo, satin bow tie, white shirt, polished oxford shoes.
How to style it: Ensure jacket fits snug. Add cufflinks. Keep accessories minimal.
When to wear: Ideal for galas, weddings, or evening receptions.
10. Summer Polo Match Attire
Light fabrics and pastel tones shine in this outfit.
Key pieces: Linen blazer, pastel shirt, white trousers, suede loafers.
How to style it: Go sockless with loafers. Add a silk pocket square.
When to wear: Garden parties, polo matches, or outdoor summer weddings.
11. Autumn Stroll Look
Warm shades and textures define fall outfits.
Key pieces: Brown wool blazer, turtleneck, grey trousers, suede loafers, scarf.
How to style it: Let scarf drape casually. Stick with earthy tones.
When to wear: Evening walks, coffee dates, or fall travel.
12. Relaxed Boat Club Outfit
Smart casual works best here.
Key pieces: White button-down shirt, navy chinos, leather boat shoes, belt.
How to style it: Roll sleeves. Match belt with shoes. Hold a glass of scotch for flair.
When to wear: Club gatherings, dinners by the water, or weekend getaways.
13. Timeless Business Casual
This look strikes the right balance of sharp and relaxed.
Key pieces: Navy blazer, striped shirt, beige trousers, brown loafers.
How to style it: Keep shirt tucked. Add slim silk tie.
When to wear: Business lunches, travel days, or office events.
14. Ski Lodge Style
Cozy and functional at once.
Key pieces: Cable-knit turtleneck, wool trousers, shearling jacket, fur boots.
How to style it: Keep colors cream and grey. Add cocoa mug for mood.
When to wear: Ski trips, winter cabins, or alpine lodges.
15. Garden Party Ensemble
Lighter tones keep the outfit fresh.
Key pieces: Pastel linen suit, white shirt, loafers, straw fedora.
How to style it: Skip socks with loafers. Hold a champagne glass.
When to wear: Summer parties, weddings, or brunches.
16. University Library Outfit
Scholar style never fades.
Key pieces: Corduroy blazer, Oxford shirt, wool trousers, tassel loafers, glasses.
How to style it: Roll shirt sleeves. Keep blazer unstructured.
When to wear: Libraries, academic meetings, or casual city visits.
17. Equestrian Inspired Look
Heritage sports influence this style.
Key pieces: Riding jacket, beige jodhpurs, leather boots, gloves.
How to style it: Keep jacket fitted. Add leather belt.
When to wear: Horse shows, estate visits, or countryside events.
18. Evening Cocktail Party
Sophistication without the tux.
Key pieces: Double-breasted blazer, cream shirt, grey trousers, polished loafers.
How to style it: Keep blazer buttoned. Hold a martini glass.
When to wear: Cocktail parties, dinner events, or holiday gatherings.
19. Spring Garden Walk
Soft colors fit the season.
Key pieces: Cream cardigan, striped shirt, pastel trousers, suede loafers, straw hat.
How to style it: Keep tones light. Use soft fabrics.
When to wear: Park walks, spring festivals, or travel.
20. Casual Weekend Getaway
Relaxed but sharp.
Key pieces: Navy sweater, khaki shorts, boat shoes, belt, sunglasses.
How to style it: Pair with a vintage car backdrop.
When to wear: Road trips, coastal towns, or weekends away.
21. Heritage Country Estate Outfit
Formal and historic.
Key pieces: Tweed three-piece suit, silk tie, pocket watch, leather brogues.
How to style it: Stick to deep earth tones. Keep vest fitted.
When to wear: Estate events, family gatherings, or weddings.
22. Yacht Club Evening Attire
Luxury meets tradition.
Key pieces: White dinner jacket, black trousers, satin bow tie, patent shoes.
How to style it: Ensure jacket fits slim. Stand on yacht deck.
When to wear: Evening yacht parties or luxury dinners.
23. Autumn Hiking Look
Rugged yet refined.
Key pieces: Waxed cotton jacket, plaid shirt, wool trousers, leather boots.
How to style it: Add binoculars. Stick with warm colors.
When to wear: Country hikes, autumn travel, or outdoor events.
24. Business Formal Elegance
Workwear at its peak.
Key pieces: Charcoal suit, white shirt, silk tie, black oxfords.
How to style it: Keep suit pressed. Add leather portfolio.
When to wear: Important meetings, formal business trips, or interviews.
25. Casual Polo and Blazer Combo
Simple yet polished.
Key pieces: Navy blazer, white polo shirt, beige chinos, brown loafers.
How to style it: Add silk pocket square. Lean against vintage car.
When to wear: Smart casual dinners, weekend city outings, or travel.
What Defines Old Money Style for Men?
Before diving into outfits, it helps to know what makes this style different.
- Neutral colors like navy, beige, cream, and grey are common.
- Tailored fits matter more than loud designs. Clothes should drape cleanly.
- Quality fabrics such as wool, cotton, linen, and cashmere stand out.
- Simple accessories like leather belts, silk ties, and subtle watches finish the look.
- Minimal branding is key. Logos and loud labels are avoided.
The focus is always on subtle refinement, not trends.
Style Tips for Old Money Outfits
- Invest in quality fabrics. Wool, linen, and cashmere last longer.
- Keep tailoring sharp. Fit is more important than brand.
- Stick with neutral palettes. Navy, beige, cream, grey, and brown always work.
- Avoid loud logos. Subtlety is part of old money style.
- Focus on timeless accessories. Leather belts, silk ties, and vintage watches.
Final Thoughts
Old money style is not about chasing trends. It is about wearing clothes that fit well, last long, and never go out of style. From navy blazers to tweed jackets, these 25 outfits show how men can look polished in any setting.
With the right fabrics, colors, and accessories, you can build a wardrobe that always looks sharp. Old money fashion is simple: quiet elegance, timeless pieces, and confidence in your style.
FAQs
What is the old money style for men?
Old money style for men is classic and understated. It focuses on tailored clothing, neutral colors, and high-quality fabrics without flashy logos or trends.
How do I dress like old money on a budget?
Choose timeless pieces like navy blazers, Oxford shirts, chinos, and loafers. Shop second-hand stores for quality fabrics such as wool, linen, and cotton. Avoid loud patterns or trendy designs.
What colors define old money fashion?
The most common colors are navy, beige, cream, grey, and brown. Pastel shades appear in spring and summer outfits, while deeper tones work for fall and winter.
Are logos part of old money outfits?
No. Old money style avoids visible branding. The focus is on fit, fabric, and timeless design rather than flashy logos or designer labels.
What shoes fit old money style?
Loafers, brogues, oxfords, boat shoes, and leather boots are staples. Shoes should be leather or suede, polished, and simple in design.
Can I wear sneakers with old money outfits?
Yes, but keep them minimal. White leather sneakers or canvas tennis shoes work for casual outfits, especially during summer. Avoid bright or chunky sneakers.
What fabrics should I look for in old money style?
Wool, cashmere, cotton, tweed, and linen are best. These fabrics hold shape, feel comfortable, and last longer than synthetic options.
Is old money style the same as preppy style?
They overlap but are not identical. Preppy style is rooted in Ivy League and college fashion. Old money style is broader, also including country estate, sailing, and formal evening looks.
Can old money outfits work for modern offices?
Yes. A navy blazer, white shirt, beige chinos, and loafers fit perfectly in business casual settings. A charcoal suit and silk tie work for formal offices.
How should I accessorize with old money style?
Stick with simple, timeless items like leather belts, silk ties, classic watches, cufflinks, and pocket squares. Avoid oversized jewelry or trendy accessories.
When is the best time to wear a tweed jacket?
Tweed works best in fall and winter. It pairs well with wool trousers, leather boots, and layered shirts, giving warmth and style in cooler months.
Are pastel colors part of old money fashion?
Yes, but only in spring and summer. Light blue, pale pink, cream, and soft green appear in garden parties, sailing outfits, and polo match looks.
How important is tailoring in old money style?
Very important. Even a simple shirt and blazer look refined when tailored. Clothes should fit the body without being too tight or too loose.
Can I mix old money style with modern trends?
Yes, but keep the balance. Add one modern item, like slim chinos or minimalist sneakers, while keeping the rest of the outfit classic.