20 Old Money Brands for Men: Old Money Fashion Style by Tier

The Verdict

The single best money-saving move in old money dressing: don't buy head-to-toe at any single tier. A Loro Piana sweater over a Uniqlo OCBD over Spier & Mackay trousers reads more old money than a $5,000 single-brand fit. The look is about restraint, palette, and silhouette — not the receipt.

The shortest path to the foundation, by category:

1. Tailoring (blazers, suits, sport coats): Spier & Mackay (~$298–498) — the best half-canvassed tailoring under $500. Step up to Drake's Games (~$1,495) when ready.
2. OCBDs and dress shirts: Mercer & Sons (~$165) for the truest unlined collar; Spier & Mackay (~$60) at the entry tier; Drake's (~$185) for the upgrade.
3. Cashmere knitwear: Uniqlo 100% Cashmere Crewneck (~$130) is the best value in menswear, full stop. Anchor purchase: one Loro Piana Roadster (~$1,295) or Brunello Cucinelli (~$1,495) per decade.
4. Trousers: Drake's Officer Chino (~$295) or Spier & Mackay (~$160). Skip anything with stretch.
5. Loafers: G.H. Bass Larson (~$175) at entry; Crockett & Jones Boston (~$680) lifetime. Brown suede first, dark brown calf second.
6. Belts and small leather goods: Anderson's of Italy (~$175) — the only belt brand that reliably matches old money shoes.

For where these brands fit in real outfits, see the old money outfits guide. For the color rules every brand below assumes you're following, see the old money color palette.

What Not to Buy

Skip these regardless of brand or tier.

1. Anything with a visible logo. Polo Bear sweaters, big Lacoste crocodiles, Gucci stripes, monogram canvas. A logo-free Uniqlo cashmere is more old money than a logo-heavy designer piece.
2. Standard-line Polo Ralph Lauren with the Polo player. Preppy, not old money. The line you want is Ralph Lauren Purple Label — fully canvassed, often Italian-made, no visible logo.
3. Brooks Brothers' trend-driven sub-lines. Stick to the heritage Made-in-USA OCBDs and Golden Fleece tailoring. Skip "Red Fleece" and the discount mall lines.
4. Anything described as "athleisure prep" or "techwear." Performance fabrics defeat the entire heritage premise.
5. Designer sneakers with chunky soles or visible logos. Common Projects Achilles (~$425), vintage Stan Smith (~$100), or Tretorn Nyliter (~$80). Nothing else.
6. "Old money" Amazon dropships. Look for natural-fiber composition (100% cotton, wool, cashmere, linen) on the label — never polyester or "wool blend" with mystery synthetic content.
7. Brunello Cucinelli outlet sweatsuits. Brand presence does not equal aesthetic. Stick to BC's tailoring and knitwear.
8. Anything you have to convince yourself is "old money enough." If you have to argue for it, skip it.

Tier 1 — Heritage Pinnacle ($$$$)

The peak of menswear. Hand-canvassed construction, the world's best fibers, generations-old Italian and English ateliers. Anchor pieces, not foundation purchases — buy one per decade if at all.

• Loro Piana (Italian) — Cashmere from Mongolia, vicuña from Peru, the absolute apex of natural-fiber knitwear. The Roadster cashmere bomber (~$3,995) and Andre cardigan (~$1,995) are the platonic ideals of old money knitwear. Their Open Walk suede loafer (~$1,395) is a desert-island purchase.
• Brunello Cucinelli (Italian) — Solomeo-village construction, the best knitwear after Loro Piana, the most refined neutrals in the business. The cashmere cable-knit (~$1,795) is the standard against which every other cable is measured.
• Hermès (French) — Beyond the leather goods, Hermès tailoring and knitwear are quietly extraordinary. The double-faced cashmere coat (~$6,500) is a lifetime purchase.
• Kiton (Italian) — Hand-tailored Neapolitan suits with soft shoulders and surgeon cuffs (~$5,000+). Worn by people who don't post on Instagram.
• Cifonelli (French/Italian) — The most distinctive shoulder in tailoring (the "cigarette" sleeve). Bespoke or made-to-measure only (~$8,000+ entry).
• Anderson & Sheppard (English) — The drape cut, soft tailoring, and the bespoke house behind Prince Charles's wardrobe. Bespoke only (~$6,500+).
• Edward Green / John Lobb (English) — The peak of dress footwear. The Edward Green Piccadilly loafer (~$1,400) and John Lobb Lopez (~$1,775) are the answers when "lifetime" means lifetime.

Tier 2 — Modern Quiet Luxury ($$$)

Where old money sensibilities meet contemporary minimalism. The sweet spot for one-anchor-per-year buying.

• The Row (American) — Olsen-twin label. Drape-y cashmere, oversized but tailored, monastic neutrals. The men's cashmere crewneck (~$1,290) is the modern standard.
• Auralee (Japanese) — Best-in-class natural-fiber basics. The cashmere crewneck (~$895) is a religious experience.
• Lemaire (French/Belgian) — Soft tailoring, muted palette, an unmistakable old-money-meets-quiet-luxury identity.
• Polo Ralph Lauren Purple Label (American) — Fully canvassed, often Italian-made, no visible logos. The American answer to Brunello Cucinelli at slightly lower price points. Italian Cashmere Crewneck (~$498), Polo II blazer (~$1,995).
• Drake's (English) — Knit ties, soft Neapolitan-inspired tailoring, OCBDs, repp ties. Drake's is the modern reincarnation of mid-century English elegance. Cotton OCBD (~$185), Officer Chino (~$295), Games sport coat (~$1,495), grenadine knit tie (~$165).
• Anderson's of Italy (Italian) — The belts. Suede or calf belt (~$175) is the only belt that reliably matches the old money shoe lineup.
• Crockett & Jones (English) — The most accessible English Goodyear-welted footwear. Chelsea 8 (~$680), Boston penny loafer (~$680), Pembroke brogue (~$680) are the foundation of an old money shoe rotation.

Tier 3 — Classic American ($$)

The bedrock of American old money dressing. Most pieces are accessible at full retail and unbeatable on sale or second-hand.

• Brooks Brothers — The original American old money brand. Madison-fit OCBD (~$140), Golden Fleece blazer (~$1,498), and grey-flannel trousers. Stick to the heritage Made-in-USA lines; skip Red Fleece.
• J.Press — More academic and Ivy League than Brooks Brothers. Shaggy-dog Shetland sweater (~$215), tweed sport coats (~$795), the original sack suit.
• Polo Ralph Lauren (standard line) — Polo shirts, cable knits, and chinos are old money staples. Be choosy: avoid pieces with the polo player logo on the chest.
• L.L.Bean Signature — Maine prep heritage. Boat shoes (~$129), blucher mocs (~$199), cable-knit sweater (~$159), Bean boots (~$159).
• Sid Mashburn (Atlanta) — Best off-the-rack American tailoring at the price. Kincaid suit (~$1,295), No. 1 jacket (~$795), Mashburn-fit chinos (~$165).
• Mercer & Sons — The truest unlined OCBD in the business, made in the USA, fits like 1960s originals. Shirt (~$165) and nothing else — they only make OCBDs.
• Allen Edmonds — Goodyear-welted American footwear. Randolph penny loafer (~$425), McAllister wingtip (~$425).

Tier 4 — Accessible Old Money ($)

The full look on a budget. Restraint matters more than spending. Build the foundation here.

• Uniqlo (cashmere, premium cotton) — The cashmere crewnecks are the single best value in menswear. 100% Cashmere Crewneck (~$130), Premium Lambswool Crewneck (~$70), Smart Ankle Pants (~$50), Supima Cotton Crewneck (~$25). Stick to navy, oatmeal, forest, burgundy.
• J.Crew — Hit or miss, but the Ludlow blazer (~$498), Bowery chinos (~$98), Heritage OCBD (~$98) deliver the look at accessible prices.
• Spier & Mackay (Canadian) — Half-canvassed suits and sport coats for $298–498 — the best entry-level tailoring on the market. Cotton/Lyocell Chino (~$98), Non-Iron OCBD (~$60), Half-Canvas Hopsack Blazer (~$298).
• Charles Tyrwhitt (English) — Constant 4-for-$200 sale prices. Their non-iron OCBD (~$50 on sale) is widely considered the best in the budget tier.
• Lands' End — Boring on the surface, but the chinos, cashmere, and outerwear punch far above their price. Look for the Squall jacket (~$179) for fall layering.
• G.H. Bass — The original American penny loafer. Larson Weejuns (~$175) is the entry-level brown suede penny.
• Vintage / Thrifted — eBay searches for "Brooks Brothers blazer 42R", "J.Press tweed", "Polo cable knit XL", or "Allen Edmonds 10D" return original-construction pieces at 80–90% off retail.

How to Shop Smart

1. Buy fewer, better pieces. One $400 cashmere crewneck worn 200 times beats ten $40 sweaters worn twice.
2. Shop second-hand for heritage brands. Brooks Brothers, Polo, J.Press, Allen Edmonds flood eBay weekly. A 1990s Made-in-USA Brooks Brothers blazer for $80 outclasses most $500 contemporary jackets.
3. Tailor everything. A $60 alteration on a $200 jacket beats a $1,200 piece you never alter. Find a local tailor and use them.
4. Mix tiers, never head-to-toe luxury. A Loro Piana sweater over a Uniqlo OCBD over Spier & Mackay trousers reads more old money than a $5,000 single-brand fit.
5. Avoid logos at every tier. A logo-free Uniqlo sweater is more old money than a logo-heavy designer piece. This is the rule that separates "old money" from "old money cosplay."
6. Anchor purchases come last. Build the entire foundation at Tier 3/4 before buying any single Tier 1 piece. The ratio that works: 1 anchor piece per 10 foundation pieces.

For a complete styling system using these brands in real outfits, see the old money outfits guide and the color palette guide.

FAQ

What brands do old money men actually wear?

Brooks Brothers, J.Press, Polo Ralph Lauren (Purple Label more than standard), Drake's, Loro Piana, Brunello Cucinelli, Hermès, Sid Mashburn, Mercer & Sons, Crockett & Jones, Edward Green — and a lot of vintage and bespoke. The common thread: heritage construction, natural fabrics, zero visible logos.

What's the most "old money" brand?

Loro Piana. Cashmere from Mongolia, vicuña from Peru, a single zip-up cardigan that costs $3,000 with no logo anywhere. Brunello Cucinelli is its closest competitor — both Italian, both built on natural fibers and quiet construction.

Can you do old money on a budget?

Yes. The look is more about palette and silhouette than price. Uniqlo cashmere (~$130), J.Crew Ludlow (~$498), Spier & Mackay tailoring (~$298), and well-curated vintage Brooks Brothers from eBay can build a complete old money wardrobe under $1,500.

Are Polo Ralph Lauren and Polo Ralph Lauren Purple Label the same thing?

No. Standard Polo (and the polo player logo) is preppy, not old money. Polo Ralph Lauren Purple Label is the high-end, fully-canvassed line — actual old money territory, often made in Italy, with no visible logo.

Is Brooks Brothers still old money?

Yes — but only the heritage lines. Despite the financial reorganization, the core Madison-fit OCBDs, Golden Fleece tailoring, and grey-flannel trousers remain the standard for American old money dressing. Avoid the trend-driven Red Fleece sub-line and the outlet/mall stock.

What old money brands work best in summer?

Loro Piana linen, Drake's short-sleeve polos and unstructured Games sport coats, Sid Mashburn unstructured tailoring, Brooks Brothers seersucker, and Polo Ralph Lauren Mercer-fit chinos. Cream, stone, and white become the dominant colors.

Are old money brands the same as quiet luxury brands?

Heavy overlap, not identical. Old money brands skew toward heritage construction (Brooks Brothers, J.Press, Loro Piana). Quiet luxury skews toward minimalist contemporary cuts (The Row, Lemaire, Auralee). For the deep dive see quiet luxury vs old money. For the opposite end of the spectrum, see old money vs new money fashion.

What's the single best entry-level old money purchase?

A Uniqlo 100% Cashmere Crewneck (~$130) in cream, navy, or oatmeal. It's the highest-leverage purchase you can make — the texture, palette, and silhouette of the heritage tier at a fraction of the price. If you only buy one piece this year, make it that.

Italian vs British vs American old money brands — which should I buy?

They each occupy a distinct lane: Italian (Loro Piana, Brunello Cucinelli, Cesare Attolini) leads on luxury knitwear, soft tailoring, and cashmere — the most expensive but the most refined. British (Drake's, Anderson & Sheppard, Crockett & Jones, Trickers) leads on structured tailoring, ties, dress shoes, and waxed cotton outerwear — the most heritage-rigorous. American (Brooks Brothers, J.Press, Mercer & Sons, Alden) leads on Ivy League prep, OCBDs, blazers, and penny loafers — the most accessible and the foundation of the entire old money aesthetic. Build on American, accent with British, splurge on Italian.

Are Loro Piana cashmere sweaters worth $1,500?

If you wear cashmere weekly for 10+ years, yes — Loro Piana uses the longest, finest cashmere fibers (15.5 micron baby cashmere from Inner Mongolia), so the sweaters resist pilling, retain shape decades longer than mid-tier cashmere, and develop a softer hand over time. If you wear cashmere occasionally and don't notice the difference between a $130 and $1,500 sweater on yourself, no — a Uniqlo cashmere crewneck delivers 80% of the visual look at 10% of the price. The honest test: handle both in person before buying. Most men don't tactilely distinguish them enough to justify the spread.