Iconic Old Money Outfits Men Should Add to Their Wardrobe
Old money style for men is all about quiet confidence, impeccable tailoring, and timeless pieces that never go out of fashion. It’s less about flashy logos and more about refined craftsmanship, quality fabrics, and a neutral, polished palette.
Whether you’re dressing for a casual weekend yacht trip, a formal business meeting, or an elegant evening event, these 21 outfit ideas capture the essence of understated luxury and effortless sophistication.
1. Navy Blazer & Khaki Chinos
Combo: Navy wool blazer + beige chinos + white Oxford shirt + brown leather loafers
Style note:
Keep the shirt neatly tucked and add a leather belt matching your loafers. A classic watch completes the outfit.
Why it works:
This combination is a cornerstone of old money menswear — polished but relaxed, perfect for everything from casual business to social events.
2. White Dress Shirt & Grey Flannel Trousers
Combo: Crisp white dress shirt + grey flannel trousers + black oxford shoes
Style note:
Opt for a slim fit shirt and trousers that break just at the shoe. Add a leather belt and silver cufflinks for subtle sophistication.
Why it works:
The clean contrast between white and grey is timeless. Flannel adds texture and warmth, making this a great option for cooler months.
3. Cashmere Sweater & White Button-Down
Combo: Camel cashmere crewneck sweater + white button-down shirt + dark denim jeans + desert boots
Style note:
Let the shirt collar and cuffs peek out for layered interest. Stick to neutral tones and minimal accessories.
Why it works:
Combining luxury fabrics with casual pieces creates an elevated but approachable look ideal for weekend outings.
4. Tailored Suit & Pocket Square
Combo: Navy or charcoal tailored suit + light blue dress shirt + leather oxford shoes + silk pocket square
Style note:
Keep the tie slim and the pocket square understated — think white with a thin navy border. A quality leather briefcase adds polish.
Why it works:
A well-tailored suit is the ultimate expression of old money style — refined, confident, and perfectly proportioned.
5. Linen Shirt & Lightweight Trousers
Combo: White linen button-down + light beige trousers + suede loafers
Style note:
Roll sleeves for a relaxed look. Add aviator sunglasses and a woven belt for summer elegance.
Why it works:
Linen breathes well and looks effortlessly chic, ideal for warm-weather events or seaside weekends.
6. Polo Shirt & Tailored Shorts
Combo: Navy polo shirt + khaki tailored shorts + boat shoes
Style note:
Tuck in the polo for a neat finish. Add a leather strap watch and a canvas belt.
Why it works:
This outfit perfectly captures casual, preppy style — comfortable yet polished for a day on the yacht or at a country club.
7. Tweed Jacket & Dark Jeans
Combo: Brown tweed blazer + white Oxford shirt + dark straight-leg jeans + leather brogues
Style note:
Choose a tweed jacket with subtle patterns and keep accessories simple. A leather messenger bag completes the look.
Why it works:
Tweed brings texture and heritage, while jeans keep it modern and wearable for weekends or casual Fridays.
8. Cashmere Overcoat & Scarf
Combo: Charcoal cashmere overcoat + navy wool scarf + tailored trousers + leather boots
Style note:
Keep the scarf loosely draped for a casual yet elegant vibe. Leather gloves add a refined touch.
Why it works:
A cashmere overcoat is an investment piece that elevates any cold-weather outfit with warmth and style.
9. Chambray Shirt & Beige Chinos
Combo: Light blue chambray shirt + beige chinos + white sneakers
Style note:
Roll sleeves and leave the shirt untucked for relaxed weekends. A canvas backpack adds practicality.
Why it works:
Casual but neat, this look blends comfort and style, perfect for weekend errands or casual outings.
10. Black Turtleneck & Gray Suit
Combo: Black fine-knit turtleneck + gray wool suit + black leather dress shoes
Style note:
Skip the tie for modern elegance. Keep accessories minimal with a sleek leather belt and watch.
Why it works:
The turtleneck under a suit adds a fresh twist to classic menswear — sophisticated and fashion-forward.
11. White Tee & Blazer
Combo: White crew neck t-shirt + navy blazer + dark jeans + loafers
Style note:
Tuck the tee in slightly and add a leather belt. A minimalist watch keeps it refined.
Why it works:
This blend of casual and tailored pieces creates a smart-casual look that’s perfect for many occasions.
12. Cable Knit Sweater & Wool Trousers
Combo: Cream cable knit sweater + charcoal wool trousers + leather derby shoes
Style note:
Add a leather strap watch and keep the sweater slightly fitted for a polished look.
Why it works:
Cozy yet refined, this combination is great for fall and winter while maintaining an elegant silhouette.
13. Seersucker Suit & White Shirt
Combo: Light blue seersucker suit + white dress shirt + brown loafers
Style note:
Keep the look fresh and light with minimal accessories. Sunglasses and a straw fedora add summer charm.
Why it works:
Seersucker fabric is breathable and stylish — ideal for warm-weather events where you want to look sharp and stay cool.
14. Denim Jacket & Khakis
Combo: Classic indigo denim jacket + white tee + khaki chinos + white sneakers
Style note:
Layer over a crisp tee and add a leather strap watch for a casual but put-together vibe.
Why it works:
Denim jackets are timeless and versatile, pairing perfectly with chinos for laid-back sophistication.
15. Oxford Shirt & Sweater Vest
Combo: Light blue Oxford shirt + navy wool sweater vest + gray trousers
Style note:
Keep the collar neat and add a leather belt matching your shoes. A pocket square adds a subtle nod to formality.
Why it works:
Sweater vests are making a comeback and add a vintage touch that fits perfectly with old money aesthetics.
16. White Dress Shirt & Navy Trousers
Combo: Crisp white dress shirt + navy tailored trousers + brown oxford shoes
Style note:
Add a slim leather belt and a classic watch. Keep sleeves neatly buttoned and shirts tucked in.
Why it works:
Simple, clean, and elegant — this look is perfect for office days, casual meetings, or evening dinners.
17. Harrington Jacket & Chinos
Combo: Beige Harrington jacket + white polo shirt + olive chinos + loafers
Style note:
Keep the jacket zipped halfway and add a leather strap watch. Sunglasses add a stylish touch.
Why it works:
The Harrington jacket is a timeless casual layering piece that blends perfectly with tailored chinos.
18. Wool Peacoat & Scarf
Combo: Navy wool peacoat + plaid wool scarf + dark jeans + leather boots
Style note:
Drape the scarf casually and add leather gloves for a polished cold-weather look.
Why it works:
A wool peacoat is classic outerwear that pairs well with casual or semi-formal ensembles.
19. Cashmere Cardigan & Dress Shirt
Combo: Light grey cashmere cardigan + white dress shirt + navy trousers
Style note:
Wear the cardigan open or buttoned halfway. Add a leather belt and classic watch.
Why it works:
Layering cashmere adds warmth and luxury without sacrificing elegance or comfort.
20. White Polo & Tailored Jeans
Combo: White fitted polo shirt + dark tailored jeans + brown loafers
Style note:
Tuck in the polo and add a leather belt. Keep accessories minimal — a leather strap watch and simple cuff bracelet work well.
Why it works:
A neat polo paired with tailored jeans is sporty yet refined, perfect for casual but upscale settings.
21. Tailored Double-Breasted Blazer & Wool Trousers
Combo: Navy double-breasted blazer + grey wool trousers + black oxford shoes
Style note:
Keep the blazer buttoned and add a silk pocket square for a polished finish. Keep accessories subtle.
Why it works:
Double-breasted blazers add a touch of old-school elegance and authority — perfect for formal occasions or business events.
FAQs About Old Money Outfits
1. What are old money outfits and how can I style them?
Old money outfits feature timeless pieces, neutral tones, and elegant accessories, creating polished, sophisticated, and effortlessly luxurious looks for any occasion.
2. How can men create old money outfits that look refined?
Old money outfits men pair tailored blazers, crisp shirts, chinos, and polished shoes for a classic, elegant, and timelessly stylish appearance.
3. What are old money outfits women that look chic and elegant?
Old money outfits women include tailored dresses, skirts, blouses, and structured layers for a sophisticated, classic, and polished style suitable for any event.
4. How do I style old money outfits dress for formal occasions?
Old money outfits dress styles combine fitted cuts, high-quality fabrics, and minimal accessories to create classy, polished, and refined formal looks.
5. What are casual old money outfits for everyday wear?
Casual old money outfits mix tailored pants, knitwear, blouses, and simple accessories to achieve an elegant, relaxed, and sophisticated style for daily life.
6. How can mens old money outfits look stylish yet understated?
Mens old money outfits include crisp shirts, tailored trousers, loafers, and minimal accessories for refined, timeless, and effortlessly polished looks.
7. What are women’s old money outfits that balance elegance and comfort?
Women’s old money outfits combine blazers, skirts, tailored pants, and soft fabrics for sophisticated, polished, and comfortable everyday or office-ready looks.
8. How do old money outfits male styles maintain a luxurious feel?
Old money outfits male pair tailored jackets, crisp shirts, elegant trousers, and refined accessories for timeless, polished, and upscale everyday style.
9. How can I wear summer old money outfits to stay cool and chic?
Summer old money outfits use lightweight fabrics, airy blouses, skirts, and minimal accessories to maintain elegance, comfort, and a polished summer-ready look.
10. What are old money outfits for women that work for multiple occasions?
Old money outfits for women feature versatile skirts, dresses, blouses, and blazers to create sophisticated, polished, and stylish looks for both work and events.
11. How do old money outfits female styles look elegant and timeless?
Old money outfits female combine classic silhouettes, high-quality fabrics, and subtle accessories for refined, polished, and timelessly stylish looks.
12. How do I choose old money outfits for men for professional settings?
Old money outfits for men include tailored suits, crisp shirts, polished shoes, and minimal accessories for confident, classic, and professional looks.
13. What are men’s old money outfits for casual yet sophisticated style?
Men’s old money outfits use tailored chinos, crisp shirts, loafers, and simple accessories to maintain a refined, classic, and polished casual look.
14. How can casual old money outfits men balance relaxed and elegant style?
Casual old money outfits men pair polos, tailored trousers, light sweaters, and loafers to achieve a stylish, timeless, and effortlessly refined appearance.
15. How do plus size old money outfits look flattering and chic?
Plus size old money outfits use tailored pieces, structured fabrics, and simple accessories to create polished, elegant, and sophisticated looks for all body types.
16. What are winter old money outfits that stay warm and stylish?
Winter old money outfits feature wool coats, tailored sweaters, trousers, and scarves for a cozy yet polished and sophisticated cold-weather look.
17. How can casual old money outfits women look stylish without trying too hard?
Casual old money outfits women pair blouses, skirts, tailored pants, or knitwear with minimal accessories for an effortless, polished, and refined everyday style.
18. What are rich old money outfits men that convey luxury and sophistication?
Rich old money outfits men combine tailored suits, crisp shirts, polished shoes, and refined accessories to achieve a timeless, upscale, and elegant look.