Style Guide · Business Casual

Old Money

Understated inherited wealth. Nothing new, nothing loud. Quality over logo.

Old Money
100
Ivy League
70
Quiet Luxury
80
01

The Wardrobe

14 pieces
Jackets & Blazers
Start here
Navy Blazer

The single most versatile piece in prep. Gold buttons optional. Works with everything.

€€€ 🌿 Spring Business Casual
Expensive
Timeless
Try-hard
Tweed Sport Coat

Harris Tweed or herringbone. The British countryside in jacket form.

€€€ 🍂 Autumn Smart Casual
Expensive
Timeless
Try-hard
Shirts
White Dress Shirt

Classic white poplin. The backbone of formal and business looks.

€€ ◈ All Formal
Expensive
Timeless
Try-hard
Knitwear
Cashmere Sweater

The quiet luxury essential. Crew or V-neck. Neutral palette. Brunello Cucinelli territory.

€€€€ ❄️ Winter Smart Casual
Expensive
Timeless
Try-hard
Trousers
Flannel Trousers

Grey flannel. The mark of a man who understands tailoring. Dress up or down.

€€€ ❄️ Winter Business Casual
Expensive
Timeless
Try-hard
Pleated Trousers

Single pleat, high rise. Old money uniform. Currently experiencing a justified revival.

€€€ ◈ All Business Casual
Expensive
Timeless
Try-hard
Shoes
Start here
Penny Loafers

The quintessential Ivy shoe. Brown or burgundy leather. With or without penny.

€€ 🌿 Spring Smart Casual
Expensive
Timeless
Try-hard
Suede Loafers

Tan or camel suede. Summer and spring. The quiet luxury version of the loafer.

€€€ 🌿 Spring Smart Casual
Expensive
Timeless
Try-hard
Tassel Loafers

More formal than penny. Alden or Bass. A step up the prep hierarchy.

€€€ 🌿 Spring Business Casual
Expensive
Timeless
Try-hard
Outerwear
Camel Overcoat

The old money winter signature. Long, structured, unmistakably wealthy.

€€€€ ❄️ Winter Semi-Formal
Expensive
Timeless
Try-hard
Trench Coat

Burberry or equivalent. British classic. Beige or stone. Timeless.

€€€ 🌿 Spring Business Casual
Expensive
Timeless
Try-hard
Accessories
Classic Dress Watch

Simple dial, leather strap. No date window preferred. Timex to Patek — it's about restraint.

€€€€ ◈ All Smart Casual
Expensive
Timeless
Try-hard
Leather Briefcase or Satchel

Tan or brown leather. Aged is better. The old money carry, never a nylon backpack.

€€€ ◈ All Business Casual
Expensive
Timeless
Try-hard
Pocket Square

White linen for formal. Printed silk for smart casual. Never matching the tie.

€€ ◈ All Smart Casual
Expensive
Timeless
Try-hard
02

Build Your Wardrobe

Three stages
Foundation Stage 1
1.
Navy Blazer
€€€ · Jacket
3.
Suede Loafers
€€€ · Shoe
Intermediate Stage 2
1.
Camel Overcoat
€€€€ · Outerwear
2.
Flannel Trousers
€€€ · Trouser
3.
Cashmere Sweater
€€€€ · Knitwear
Mastery Stage 3
1.
Pleated Trousers
€€€ · Trouser
2.
Classic Dress Watch
€€€€ · Accessory
3.
Leather Briefcase or Satchel
€€€ · Accessory
03

How to Wear It

Proven combinations
Anchor piece
Cashmere Sweater
95 Flannel Trousers
90 Suede Loafers
88 Camel Overcoat
88 Navy Chinos
Anchor piece
Navy Blazer
98 Khaki Chinos
98 Oxford Cloth Button-Down
95 Flannel Trousers
95 Penny Loafers
Anchor piece
Camel Overcoat
92 Flannel Trousers
90 Turtleneck Sweater
88 Cashmere Sweater
04

What to Avoid

12 common errors
Large, visible logos on any piece
Old money dresses to signal nothing. Logos are insecurity made visible.
9/10
White athletic socks with leather shoes
The easiest way to undo an outfit. Dress socks always. No exceptions.
9/10
Athletic or running sneakers in a smart casual context
Clean court shoes (Stan Smith, Common Projects) yes. Chunky sneakers break the aesthetic entirely.
8/10
Brown belt with black shoes or vice versa
The most noticed invisible rule. Match belt leather to shoe leather always.
8/10
Slim or skinny fit on chinos or trousers
Prep silhouette is relaxed, not fitted. Slim chinos look fast-fashion, not Ivy.
8/10
Polyester or synthetic blends on main pieces
Fabric speaks. Natural fibers drape, breathe, age. Synthetic pieces look cheap immediately.
8/10
Overly baggy, shapeless fit
Expensive clothes hang well. Shapeless looks cheap regardless of brand.
7/10
Tie and pocket square matching exactly
A matched set looks catalogue, not considered. Coordinate, never match.
7/10
Too many accessories at once
Restraint is the signature of old money. One statement piece maximum.
7/10
Trousers too short (no break) or too long (puddling)
A slight break is classic. No break is modern but risky. Puddling is never acceptable.
7/10
Shoes that look brand new and unworn
Old money wears things in. Too-new shoes look like a costume.
6/10
Novelty or loud logo socks as a 'fun' detail
Quirky socks are the tech-bro substitute for genuine style. Argyle or solid only.
5/10
06

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