The VOU / Styling guides

Casual Old Money Style for Men in Five Outfit Ideas, With Do’s and Don’ts

By Mandy Meyer, Sara Law and Natalie Wilson. Reviewed and approved by Lawrence Anderson and Raf Adams. Last updated

Casual Old Money Style

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What’s This About

Casual Old Money style is relaxed, classic leisurewear: linen and Oxford shirts, polos, chinos, shorts, knitwear and loafers in quiet colours.

This guide shows how to put the casual look together, such as:

What the casual version of the look includes

A country club outfit for summer lunches

A nautical outfit for days by the sea

An Ivy League weekend outfit

Do’s and don’ts for fabrics, fit and colour

and many more!

The outfits work at any age and at many prices, and they say nothing about the wearer’s wealth or background.

Key Points

01Five complete outfits cover country club, nautical, Ivy League, garden party and Riviera settings.

02Labels are examples across price levels; similar garments that fit work as well.

03Start from neutral colours and add one or two accents such as faded red or a print shirt.

04Fit at the shoulders, collar and trouser length matters more than the label.

Casual Old Money style means relaxed, classic clothes: linen and Oxford shirts, polo shirts, chinos, shorts, knitwear and leather shoes in quiet colours.

This guide gives five complete outfit ideas for weekends, summer events and holidays, plus simple do’s and don’ts.

The outfits suit any age, and you can build them at many prices; the labels named are examples to compare, not requirements.

Like the wider Old Money label, the casual version is a way of dressing, not evidence of anyone’s wealth or background.

What the casual Old Money look is

a man walking down the street in a brown linen shirt, white drawstring trousers and brown loafers Jude Law in a white and grey knitted resort shirt and white shorts by the sea a man leaning against a pole in a camel trench coat, denim shirt, navy trousers and suede boots
a man leaning against a wood-panelled car in a light blue button-down shirt, chinos and a leather belt a man leaning against a boat in a red linen shirt and navy shorts a man standing at a stone railing by the water in a striped band-collar shirt, white shorts and white trainers
a man in a white polo shirt and white shorts a man sitting in a chair in a pink gingham shirt, navy shorts and a blue cable jumper over his shoulders a man in a blue polo shirt, white trousers and a striped belt
a man wearing a green shirt, white trousers and sandals, carrying a jacket a man in front of a large house in a navy short-sleeved linen shirt, cream chinos and white tennis trainers a man sitting in a chair on the beach in a navy polo shirt and red shorts
a man in a panama hat, aviator sunglasses, palm print shirt, woven leather belt and white trousers a man in a white Oxford shirt and khaki chinos a man leaning on a red car in a navy striped jumper, cream trousers and loafers

The casual side of the Old Money style takes classic leisure and sports clothes and keeps them simple.

Typical clothes are linen or Oxford cotton shirts, piqué polo shirts, Breton tops, chinos, linen trousers, tailored shorts, cable or crew-neck knitwear, loafers, boat shoes and plain trainers.

Colours tend to be white, cream, navy, light blue, khaki and soft pastels, with stripes, gingham and the occasional print.

The aim is clothes that are comfortable, fit well and suit the setting, whether that is a relaxed lunch, a weekend with friends or an informal evening.

A few well-chosen basics combine into many outfits, which is the idea behind a capsule wardrobe.

Five casual Old Money outfit ideas

Each outfit below is built from Old Money wardrobe essentials and lists the top, trousers or shorts, shoes and accessories.

The labels named range from high-street to luxury; similar garments from other makers, second-hand or new, work just as well if they fit.

1. The country club classic

This country club-inspired outfit suits a summer lunch, a golf day or a garden visit.

Start with light-coloured cotton or linen trousers, for example from Ralph Lauren or Peter Millar.

Cream knitted polo shirt with white trousers, a tan belt and tan loafers

Add a pastel or cream polo shirt, for example from Lacoste, tucked in for a neat line.

Wear brown or tan leather loafers and a plain leather belt in a similar shade; labels to look at range from Clarks and Bass to Tod’s and Ferragamo.

Pale pink polo shirt with white trousers, a brown belt and brown loafers

A simple watch on a leather or fabric strap finishes the outfit.

Wear: a cream polo shirt, white cotton trousers, tan penny loafers, a tan leather belt and a simple watch.

Our guides to Old Money style icons and Gianni Agnelli’s style show more examples of relaxed tailoring and leisurewear.

2. The nautical outfit

This nautical beach outfit suits a day by the sea, on a boat or at a harbour lunch.

Start with Nantucket Reds shorts, a faded red cotton associated with Murray’s Toggery on Nantucket, or tailored swim shorts in a small pattern, for example from Orlebar Brown or Vilebrequin.

Red is one accent within the Old Money colour palette, alongside navy and white.

Breton striped T-shirt with rust shorts and brown boat shoes on a boat deck

Add a navy and white Breton top, for example from Sunspel, and layer an open white linen shirt over it if the breeze picks up.

Choose boat shoes, for example from Sperry, or espadrilles, for example from Castañer or Manebí.

A braided leather bracelet and classic sunglasses are optional extras.

Wear: a navy Breton top, faded red cotton shorts, brown boat shoes without socks and an open white linen shirt as a light layer.

3. The Ivy League weekender

This outfit borrows from Ivy League campus clothes and suits a weekend in town or a cool autumn day.

Start with chinos in a neutral tone, for example from J.Crew or Bonobos, in whichever leg shape you prefer, and an Oxford cloth or chambray button-down shirt, for example from Gitman Vintage or Hamilton, with the sleeves rolled.

Patterned blue knitted jumper over a collared shirt with beige chinos and brown boots

Wear suede desert boots, for example from Clarks, and a simple leather-strap watch.

Add a cotton or wool jumper, worn or draped over your shoulders; labels to look at range from Uniqlo and J.Crew to Zanone and Brunello Cucinelli.

Wear: a white Oxford button-down, a navy crew-neck jumper, stone chinos and sand suede desert boots.

For a film reference, Alain Delon’s light blue Oxford button-down, cream jeans and suede horsebit loafers in Purple Noon (Plein Soleil, 1960), costumes by Bella Clément, are analysed by BAMF Style.

Our Preppy style guide has more campus-inspired outfits.

4. The garden party outfit

This outfit suits an outdoor party, a summer wedding reception with a relaxed dress code or a long lunch.

Start with light-coloured linen trousers, for example from Incotex or Boglioli.

Tuck in a floral or paisley shirt, for example from Etro or Paul Smith, if you enjoy pattern; a plain linen shirt is a quieter alternative.

Floral print short-sleeved shirt with white trousers and brown loafers

Add a woven leather belt, for example from Anderson’s, and brown suede loafers, for example from Crockett & Jones.

Tortoiseshell sunglasses and a linen pocket square, if you add a jacket, finish the outfit.

Wear: a floral cotton shirt, white linen trousers, a woven brown belt and brown suede loafers, with a navy unstructured blazer if the evening turns cool.

5. The Riviera outfit

This Riviera-inspired outfit suits hot weather, holidays and evenings by the sea.

Wear white or cream trousers, for example from Frame, with a striped or plain linen shirt, for example from 120% Lino or Hartford, with the top button or two undone.

White linen shirt with cream linen trousers and brown sandals

Add brown leather sandals, for example from Ancient Greek Sandals or Hereu.

A panama hat, for example from Borsalino or Lock & Co., gives shade in strong sun.

Wear: a white linen shirt, cream linen trousers, brown leather sandals and a panama hat.

For a film reference, Jude Law’s resort shirts and pleated cream trousers as Dickie Greenleaf in The Talented Mr. Ripley (1999), costumes by Ann Roth and Gary Jones, are described in detail by BAMF Style.

Casual Old Money do’s and don’ts

Do Don’t

Choose classic shapes you will wear for several summers

Try cotton, linen and wool, and check the weave and seams as well as the label

Get the fit right at the shoulders, collar and trouser length

Start from neutral colours and add one or two brighter accents

Mix textures, such as linen with knitwear

Rely on large logos to carry the outfit

Assume a fibre or a price guarantees quality

Wear clothes that pull or sag

Combine several loud patterns in one outfit

Wear every accessory you own at once

Casual style on any budget

You do not need a large budget for these outfits.

Our guide to affordable Old Money clothing brands lists lower-priced labels for each garment.

If you would like personal help, The VOU offers paid consultations, including a professional fashion style analysis.