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What’s This About
The modern Old Money look is classic menswear worn with softer tailoring, relaxed proportions and more knitwear, chosen for fit and fabric rather than logos.
This guide explains how the modern version differs and how to put it together, such as:
Softer, less structured jackets and higher-rise pleated trousers
The difference between fit and the relaxed silhouette you choose
Blazers, overcoats, knitwear and Oxford shirts to start with
Loafers, Chelsea boots and plain accessories
Four outfits for the office, weekends, summer evenings and winter dinners
and many more!
Choose the cuts you like, make sure each garment fits, and keep the colour range narrow so your clothes work together.
Key Points
01Old Money is a contemporary label for classic clothes, not a sign of anyone’s family or wealth.
02The modern version swaps stiff suits for soft tailoring, knitwear and smart-casual combinations.
03A relaxed silhouette still needs a good fit at the shoulders, waist and trouser length.
04Brand names matter less than fabric, construction, care and whether the clothes suit the setting.
The modern Old Money look takes classic menswear, such as navy blazers, Oxford shirts, wool trousers, knitwear and loafers, and wears it with today’s softer tailoring and more relaxed proportions.
It sits apart from fast, trend-driven menswear, because the clothes change slowly and can be worn for years.
This guide explains what makes the modern version different, which garments to start with, and how to wear it at work and at the weekend.
For the full season-by-season wardrobe, see our Old Money aesthetic guide.
What makes the modern version different?
Old Money is a contemporary label for classic clothes, and wearing them says nothing certain about anyone’s family or bank balance.
It is usually defined by contrast with new money style, which favours logos and fast-moving trends, and our comparison of Old Money and New Money clothing details looks at how those labels are used.
The look borrows from the American Ivy League wardrobe, from Parisian chic and from the British Sloane Ranger look.
The modern version differs from the older wardrobe in three ways.
Softer tailoring
Jackets are more often unstructured or lightly padded at the shoulder, with natural lapel rolls and less stiffness than a traditional business suit.
Structured shoulders are still an option, and our guide to how tailored clothes should fit explains what a tailor can change in either case.
More relaxed proportions
Higher-rise trousers with pleats and a fuller leg are common, worn with shorter, softer jackets and knitwear.
That is a chosen silhouette, which is different from fit: a relaxed trouser should still sit at your waist without pulling, and a slim one should still let you sit down comfortably.
See our guide to dress trousers for rise, break and width.
Knitwear and smart casual in place of suits
Many offices are less formal than they were, so the modern look leans on knitwear, blazers and chinos more than on full suits.
Colours stay restrained: navy, camel, grey and off-white, with olive, chocolate brown, burgundy or forest green as accents, as our guide to Old Money colours shows.
Tonal outfits in white, cream and beige are popular, and our guide to monochrome outfits shows how to keep them from looking flat.
Many younger buyers also look for secondhand clothes and natural fibres, a shift discussed in our guide to why Gen Z took up Old Money style.
Modern Old Money wardrobe essentials
Start with a few garments that combine easily, and add more as you find gaps.
Blazers and jackets
A navy wool blazer is the most useful jacket, worn with grey flannel trousers, off-white chinos or a fine merino jumper underneath.
Look for moderate lapels, a natural or soft shoulder and enough room to move.
A double-breasted blazer in a slightly relaxed cut is a dressier option, worn with a cotton shirt and high-waisted pleated trousers.
Pleated wool trousers in grey, taupe or navy drape well with both jackets.
Outerwear
A beige or navy trench coat works over tailoring and casual clothes in changeable weather.
A camel, navy or charcoal wool overcoat is the winter equivalent, sized to fit over a blazer or chunky knit, and our overcoat styling guide covers lengths and cuts.
A quilted jacket or waxed cotton field coat suits the country and weekends.
Our guide to Old Money style for young men has more on outerwear for a first wardrobe.
Knitwear
A cashmere or lambswool crew-neck jumper in a neutral colour goes over a shirt or under a blazer.
A fine merino roll neck works on cooler days instead of a shirt and tie.
A cable-knit jumper, a pattern associated with British and Irish knitting traditions, is the relaxed option; wear it with pleated trousers and loafers.
Shirts and polo shirts
White and light blue Oxford cloth button-down shirts are the most versatile shirts, working with tailoring and knitwear alike.
Linen shirts are cooler for summer.
Polo shirts in cotton piqué or fine merino, with small or no logos, cover casual days.
Shoes and accessories
Shoes
Choose shoes that are well made and plain, and see our dress shoes guide for construction and fit.
Penny loafers are the most versatile choice, worn with a navy blazer and pleated trousers or with linen chinos.
Calf leather or cordovan in dark brown, black or oxblood develops a patina with wear and care.
Tassel loafers are a slightly dressier alternative.
For formal events, black cap-toe Oxfords suit business meetings and evening dress codes.
For weekends and colder months, dark brown suede Chelsea boots or brogues pair well with wool overcoats and tweed.
Belts, watches and scarves
A leather belt in brown or black with a plain silver or gold buckle is enough.
A dress watch on a leather strap or a simple steel watch works with most outfits; the brand matters less than whether it suits your wrist and your clothes.
A cashmere or wool scarf in camel or charcoal finishes a winter coat, and a silk pocket square can add a little colour.
Eyewear
Classic acetate or tortoiseshell sunglasses, such as Persol’s folding 714 or Oliver Peoples’ Gregory Peck model, fit the look better than heavily branded frames.
Thin metal or plain acetate prescription frames follow the same idea, and Gianni Agnelli’s style is a useful reference for wearing accessories with ease.
Leather goods
A full-grain leather briefcase or document holder works with business clothes, and a brown or navy weekend bag works for travel.
A slim wallet or cardholder without large logos completes the set, and our list of Old Money wardrobe essentials has more ideas.
Outfits for the modern Old Money look
Office: a light blue Oxford shirt, a navy unstructured blazer, mid-grey pleated wool trousers and dark brown penny loafers, with a beige trench coat.
Weekend: a cream cable-knit jumper over a white T-shirt, olive chinos and brown suede Chelsea boots, with a waxed cotton jacket.
Summer evening: a white linen shirt, a navy linen blazer, stone pleated trousers and tan suede loafers.
Winter dinner: a charcoal merino roll neck, a brown tweed jacket, grey flannel trousers and black calf loafers, under a camel overcoat.
Grooming and manners
Grooming is tidy rather than elaborate: a regular haircut, such as the styles in our Old Money hairstyle guide, and a clean shave or a trimmed beard.
If you wear fragrance, keep it light; heritage perfume houses such as Creed, Acqua di Parma and Floris are often mentioned, but any scent you like will do.
Pressed shirts, polished shoes and clothes that fit matter more than any label.
Good manners help in any setting, but they are not tied to a wardrobe, and no one needs a particular education, holiday destination or hobby to wear these clothes well.
Take our three quizzes
None of these tools is needed to wear the outfits in this guide, but some readers like extra help when choosing clothes.
Check your body shape with the body shape quiz for men, and read our guides to the men’s body shapes and menswear silhouettes.
Find your seasonal colours with the seasonal colour quiz for men, and read more about seasonal colour palettes for men.
Take the fashion style quiz for men to see which styles and outfit ideas match what you like wearing, and see our fashion style guide for personal and historic styles.
Book a consultation for personal help
If you would like personal help after the quizzes, you can book paid consultations with The VOU’s image consultants and stylists through our styling services for men, or contact us with questions.
You can also read how to choose an image consultant, learn what an image consultant does, and see our guide to styling by occasion, location, season and time of day.
For the vocabulary used in this guide, see our explainers on clothing, garments, fashion accessories and outfits.
We also cover heritage luxury brands and how logo-heavy luxury designs come across.