Rich people have long been associated with timeless, classic fashion, particularly the styles rooted in the Old Money aesthetic.
Styles such as American Preppy, British Sloane Ranger, French BCBG, and Italian Alta Borghesia represent more than just clothing choices; they reflect a lifestyle built on subtlety, quality, and tradition.
If you’re looking to emulate the appearance of wealthy and successful men, wearing Old Money fashion styles is the only way forward.
The beauty of these looks lies in their versatility—they can be worn daily, across a range of locations and occasions, without losing their sense of refinement.
Dressing like a millionaire doesn’t have to break the bank – you can still embody the same elegance and sophistication by choosing affordable alternatives to luxury brands for ultra-rich people.
In this guide, we will explore how to dress like a rich man daily by leveraging Old-Money styles.
You’ll learn how to select the perfect outfits based on your body shape and seasonal colours and how to dress by occasion and location to maintain a relevant look.
Affordable Ways to Achieve the Rich Look
If you’re looking to dress like a wealthy man daily, relying on expensive luxury brands, without an idea of what a capsule wardrobe means or how to build one, your choice might quickly become costly.
Instead, focus on mastering the principles that guide Old Money style: timelessness, quality, and subtlety.
Old Money fashion prioritise well-fitted, versatile pieces that can be worn in various settings.
You can achieve the Old Money look affordably by choosing brands that focus on quality materials and craftsmanship but don’t carry the high price tags of ultra-luxury labels.
The key is to invest in wardrobe essentials like tailored blazers, Oxford shirts, chinos, and high-quality knitwear that will last and can be styled in various combinations.
Thrift stores and outlets offer many of these timeless pieces at a fraction of the cost, and some excellent affordable options include:
- J.Crew Factory (for tailored blazers and chinos)
- Banana Republic Factory (affordable knitwear and suits)
- Brooks Brothers Outlet (classic Oxford shirts and suits)
- Uniqlo (for quality basics like chinos, blazers, and knitwear)
- Nordstrom Rack (discounted designer items)
- Ralph Lauren Factory Store (classic polo shirts and tailored pieces)
- H&M (affordable preppy basics)
- Zara (stylish blazers and trousers)
- ASOS (affordable footwear and accessories)
- The RealReal (for second-hand luxury items)
At the same time, online retailers offer affordable alternatives that replicate the refined looks of Old Money wardrobes but pay attention to fabric quality.
Always choose natural materials like wool, cotton, and linen in classic Old Money colours, so your outfits have an elegant, polished finish.
Outfit Ideas to Dress Like a Rich Man
If you’re looking for daily outfit inspiration, here are detailed ideas to channel Old Money styles while still being affordable.
Each outfit is crafted to reflect the elegance and sophistication of wealthy men, using affordable brands without sacrificing quality.
1. American Preppy Look
To achieve the American Preppy look, start with a classic white Oxford button-down shirt from Uniqlo (£29.90) and pair it with khaki chinos from J.Crew Factory (£55).
Complete the outfit with brown penny loafers from Clarks (£70), and for a polished appearance, match it with a navy blazer from H&M (£49.99).
Accessorise with a brown leather belt from ASOS (£15) and a silver Casio MTP-VD01 watch (£30).
Overall Cost: £249.89
2. British Sloane Ranger Look
For a Sloane Ranger-inspired style, choose a tailored navy blazer from Zara (£79.99), cream pleated trousers from Marks & Spencer (£45), and a white shirt from TM Lewin (£34.95).
Pair with black brogues from Charles Tyrwhitt (£99) for that quintessential British flair.
To complete the look, add a silk scarf in a classic paisley pattern from H&M (£12.99) and carry a tan leather briefcase from ASOS (£39.99).
Overall Cost: £311.92
3. French BCBG Look
For a Parisian-inspired BCBG look, go for neutral tones and tailored cuts.
A dove grey slim-fit trousers from Mango (£39.99), a camel-colored cashmere sweater from Uniqlo (£79.90), and chestnut brown leather loafers from Aldo (£85).
Finally, top it off with a classic beige trench coat from Zara (£99.99) for that Parisian sophistication.
Overall Cost: £304.88
4. Italian Alta Borghesia Look
The Italian Alta Borghesia style is all about structured elegance.
Start with a well-fitted navy blue blazer from Mango (£69.99), light grey wool trousers from J.Crew Factory (£70), and a well-pressed white dress shirt from H&M (£19.99).
Pair with cognac brown leather oxfords from Clarks (£89), a dark brown leather belt from ASOS (£15), and a burgundy silk pocket square from Marks & Spencer (£9.99).
Overall Cost: £273.97
5. Modern Old-Money Look
This outfit blends classic and modern garments to create a contemporary old-money look.
Begin with dark indigo jeans from Uniqlo (£39.90) and a light blue Oxford cloth button-down shirt from H&M (£19.99).
Match with a navy merino wool crew neck sweater from Marks & Spencer (£35) and white leather sneakers from Aldo (£65).
Add a dark brown leather belt from ASOS (£15) and a minimalist silver-tone watch with a white dial from Casio (£25).
For outerwear, include a navy cotton twill Harrington jacket from Zara (£59.99).
Overall Cost: £259.88
6. Country Club Casual Look
The country club look blends the relaxed elegance of British aristocracy with a sporty edge.
Begin with tailored stone-colored cotton shorts from Marks & Spencer (£35) and a pale pink polo shirt from Ralph Lauren Factory Store (£49.99).
Add a navy cotton cable-knit sweater from Uniqlo (£39.90) to drape over the shoulders and white leather sneakers from the Adidas Stan Smith line (£74.95).
Accessorize with a braided fabric belt in navy and white from J.Crew Factory (£29.50) and a classic Timex Weekender watch with a navy NATO strap (£49.99).
Overall Cost: £279.33
Dressing for Your Body Shape
Understanding and dressing for your body shape is crucial to achieving a polished, confident look – if you are not sure what is your body shape, take this quick quiz.
Let’s explore how you can make the most of your unique physique.
Triangle Body Shape
If you have a triangle body shape with narrower shoulders and a wider lower body, focus on balancing your proportions:
- Wear structured jackets with shoulder padding to broaden your upper body
- Choose vertical stripes and patterns to create the illusion of height and slimness
- Wear darker colours on the bottom and lighter shades on top to draw the eye upwards
- Avoid skinny fits and opt for straight-leg trousers to create a more balanced silhouette
Inverted Triangle Body Shape
If you have an inverted triangle shape, boasting broad shoulders and a narrower waist, aim to create balance by adding volume to your lower body:
- Choose unstructured jackets to avoid emphasising shoulder width
- Opt for straight or boot-cut trousers to add volume to your legs
- Experiment with patterned or lighter-coloured trousers to draw attention downwards
- Avoid overly tight-fitting tops that accentuate your upper body disproportion
Rectangle Body Shape
If you have a rectangular body shape, characterised by similar measurements at the shoulders, waist, and hips, your goal is to create the illusion of a more defined waist:
- Utilise layering to add dimension to your silhouette
- Choose jackets with a slightly nipped waist to create the appearance of curves
- Experiment with different textures and patterns to add visual interest
- Opt for slim-fit clothing to avoid appearing boxy
Oval Body Shape
If you have an oval or apple body shape, carrying weight around your midsection, focus on creating a more streamlined silhouette:
- Choose vertical stripes and patterns to create a lengthening effect
- Opt for darker colours, especially around your midsection
- Wear well-fitted, but not tight, clothing to skim over your body without clinging
- Choose jackets and tops that end below the widest part of your body to create a slimming effect
Trapezoid Body Shape
If you have a trapezoid body shape with broad shoulders that taper to a narrower waist and hips, you’re considered to have the ‘ideal’ male physique.
The key is to maintain this balanced silhouette:
- Opt for well-fitted clothing that showcases your natural proportions
- Experiment with different styles, as most will suit your balanced frame
- Choose V-neck tops to emphasise your broad chest and shoulders
- Wear tapered trousers to complement your narrower lower body
Hourglass Body Shape
If you’re amongst men with an hourglass body shape with a well-defined waist and proportional shoulders and hips, aim to highlight your natural curves:
- Choose fitted clothing that accentuates your waist
- Opt for high-waisted trousers to showcase your proportions
- Experiment with belts to further define your waistline
- Avoid overly loose or baggy clothing that can hide your natural shape
Match Your Seasonal Colour Palette
Your seasonal colour palette is determined by your skin tone, eye colour, and natural hair colour – if you are not sure what is your seasonal colour, take this quick quiz.
Understanding your palette is critical in choosing colours that enhance your natural features and make you look more vibrant.
Aligning your wardrobe with your seasonal colour palette will create a more harmonious and flattering look.
Spring Colours
If you’re a Spring man, your palette consists of warm and bright colours:
- Opt for clear, warm shades like coral, golden yellow, and grass green
- Choose light to medium colours rather than dark or muted tones
- Pair your outfits with gold jewellery to complement your warm undertones
- Avoid black or very dark colours, which can appear harsh against your complexion
Summer Colours
If you’re a Summer man, your palette is cool and muted:
- Select soft, cool colours like powder blue, lavender, and rose pink
- Opt for pastels and muted shades rather than bright or dark colours
- Choose silver or platinum jewellery to complement your cool undertones
- Avoid orange and other warm, bright colours that can clash with your complexion
Autumn Colours
If you’re an Autumn man, your palette consists of warm, rich earth tones:
- Choose deep, warm colours like rust, olive green, and terracotta
- Opt for rich, muted shades rather than bright or pastel colours
- Wear gold or copper jewellery to enhance your warm undertones
- Avoid cool pastels or icy colours that can make you appear washed out
Winter Colours
If you’re a Winter man, your palette is cool and bright:
- Select clear, cool colours like true blue, emerald green, and deep purple
- Opt for high-contrast combinations, such as black and white
- Choose silver or white gold jewellery to complement your cool undertones
- Avoid muted earth tones or warm colours that can clash with your complexion
Dressing According to the Occasion
Your choice of attire should always be appropriate for the event or setting you’re in.
By dressing appropriately for each occasion, you’ll look your best and feel more confident and at ease in any setting.
Always consider the event’s dress code, if specified, and it’s better to be slightly overdressed than underdressed when in doubt.
Business Formal
Business formal for high-level business meetings, interviews, or corporate events.
- Wear a well-fitted dark suit (navy, charcoal, or black)
- Choose a crisp white or light blue dress shirt
- Opt for a conservative tie in a solid colour or subtle pattern
- Complete the look with polished black Oxford shoes
- Keep accessories minimal and elegant (e.g., a classic watch)
Business Casual
Business casual for less formal work environments or casual Fridays.
- Pair dress trousers or chinos with a button-down shirt
- Add a blazer or sports jacket for a more polished look
- Wear leather shoes such as loafers or brogues
- A tie is optional, but ensure your shirt collar looks neat without one
Smart Casual
Smart casual for dinner dates, theatre outings, or upscale restaurants.
- Combine dark jeans or chinos with a collared shirt
- Layer with a blazer, cardigan, or fine-knit jumper
- Choose smart leather shoes or clean, minimalist trainers
- Add subtle accessories like a leather watch or a pocket square
Casual
Casual for weekend outings, casual gatherings with friends, or relaxed settings.
- Opt for well-fitted jeans or casual trousers
- Pair with a T-shirt, polo shirt, or casual button-down
- Choose comfortable footwear like trainers or boat shoes
- Layer with a casual jacket or hoodie if needed
Black Tie
Black tie for formal evening events or galas.
- Wear a black tuxedo with satin lapels
- Choose a crisp white dress shirt with a wing or turndown collar
- Add a black bow tie and a cummerbund or waistcoat
- Complete the look with patent leather Oxford shoes
- Include subtle accessories like cufflinks and shirt studs
Dressing According to the Location
Influenced by culture, climate, and local aesthetics, fashion varies significantly globally.
While adapting to local styles can help you blend in, it’s equally important to maintain your personal style.
The key is to find a balance between respecting local fashion norms and expressing your individual taste.
London, UK
Known for its blend of tradition and contemporary style:
- Wear Savile Row tailored suits in classic cuts and in darker colours
- Incorporate British heritage fabrics like tweed and tartan
- Layer effectively to combat unpredictable weather
- Don’t shy away from eccentric accessories like pocket squares or cufflinks
Milan, Italy
Celebrated for its sartorial elegance:
- Choose well-fitted, unstructured suits in lighter fabrics
- Embrace brighter colours, modern patterns, and add your own touch of Sprezzatura.
- Pay attention to details like perfectly knotted ties and pocket squares
- Wear in high-quality leather shoes and accessories
New York City, USA
A melting pot of styles with a lean towards practicality:
- Wear versatile garments that allow transitioning from day to night
- Embrace a monochromatic palette, especially black
- You can safely incorporate touches of streetwear and athleisure into business-casual attire
- Choose statement outerwear for colder months
Tokyo, Japan
Known for its avant-garde fashion and attention to detail:
- Experiment with layering and unconventional silhouettes
- Embrace minimalist designs and muted colour palettes
- Pay attention to textile quality and craftsmanship
- Don’t be afraid to mix formal and casual elements
Mumbai, India
Characterised by vibrant colours and traditional influences:
- Incorporate bold, bright colours into your wardrobe
- Experiment with traditional garments like the Nehru jacket
- Opt for lightweight, breathable fabrics to combat the heat
- Embrace intricate patterns and embroideries
Moscow, Russia
Known for its emphasis on formal wear and luxurious fabrics:
- Invest in high-quality, warm outerwear for harsh winters
- Opt for darker, richer colours in your wardrobe
- Don’t shy away from fur elements in winter wear
- Choose formal over casual for most social occasions
São Paulo, Brazil
Characterised by a relaxed yet stylish approach:
- Embrace a more casual interpretation of business wear
- Opt for lighter fabrics and brighter colours
- Incorporate elements of beachwear into everyday style
- Choose comfortable, breathable shoes suitable for walking
Conclusion
Mastering the art of dressing well is a nuanced skill that goes beyond simply following trends or rules.
It’s about understanding and harmonising various elements to create a style that is both appropriate and authentically you.
Throughout this guide, we’ve explored the crucial aspects of building a versatile and impactful wardrobe:
- Dressing for your unique body shape to accentuate your best features
- Choosing colours that complement your natural palette
- Adapting your style to different occasions, from casual outings to formal events
- Understanding how location influences fashion, whether you’re in London, Tokyo, or São Paulo
- Considering seasonal changes and time of day in your outfit choices
Remember, true style is not about blindly following fashion dictates, but about making informed choices that suit your personal taste, lifestyle, and the contexts in which you find yourself.
It’s about feeling confident and comfortable in what you wear, while also showing respect for your environment and the people around you.
As you apply these principles, don’t be afraid to experiment and develop your unique style.
Fashion should be enjoyable, a form of self-expression that evolves with you over time.
With practice and attention, you’ll find that dressing well becomes second nature, allowing you to navigate any social situation with confidence and ease.
Find Your Personal Style
Before you go, here’s one of the best-kept secrets in men’s styling circles, a secret that only a few expert image consultants know or are willing to share.
First and foremost, professional styling requires knowing your unique body shape and seasonal colour palette, as the main factors in choosing perfectly fitting clothes in colours that complement your skin, eyes, and hair.
Only then you can be styled by occasion, location, season, and time of day, with garments, footwear, and accessories from heritage fashion brands that depict an old-money style gentleman of high confidence and success.
Best part? You can find your body shape, seasonal colour palette, and ideal fashion style, in less than 5 minutes, thanks to our 3 simple steps, below:
1. Find Your Body Shape
Different garments flatter different physiques, so knowing your body shape is the first step in dressing like a confident man – free body shape quiz for men.
Once you know your unique body shape, take the second free quiz to discover your unique colour palette.
2. Find Your Unique Colour Palette
Remember, fashion comes in various colours, but not every hue complements your natural colour.
Take our free seasonal colour quiz for men to find the most suitable colours for you.
3. Find Your Ideal Fashion Style
By now, you should already know your body shape and unique colour palette; the next step is to discover your ideal personal fashion style.
The fastest and simplest way is to take our free fashion style quiz for men; it includes your ideal style, outfit ideas, relevant fashion brands, and much more.
Professional Image Consultancy with The VOU
Only now you can style by occasion, location, season, and time of the day – here’s also where our expert image consultants and fashion stylists come in.
Our styling services for men are the most comprehensive and detailed on the market, backed up by leading stylists who will guide you step by step in creating looks that communicate affluence, elegance, and endless accomplishments.
Remember, owning luxury clothes isn’t enough; to look stylish, confident, and successful, you must first know your body shape and colour palette and only then style by occasion, location, season, and time of day.
Contact us today and save headaches, time, and money; the first styling assessment is on us!
It’s time to show the world the confident and successful you, a gentleman of exquisite fashion taste.