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How to Dress Old Money Style on a Budget – 12 Wardrobe Staples for Men

The allure of the Old Money aesthetic, with its timeless elegance and understated sophistication, is undeniable. However, achieving this look doesn’t necessarily require a trust fund.

With some savvy shopping and a focus on quality essentials, you can cultivate an Old Money wardrobe that exudes class without breaking the bank.

In this article, we’ll discuss 12 essential pieces that form the foundation of a versatile and affordable Old Money wardrobe.

1. The Classic Single-Breasted Suit

Classic Single-Breasted Suit J Crew
Classic Single-Breasted Suit – Image courtesy: J.Crew

A navy or charcoal suit is the cornerstone of any well-rounded wardrobe.

Opt for a classic two-button, single-breasted design in a mid-weight wool or wool-blend fabric.

The two-button, single-breasted design can be dressed up for formal occasions or deconstructed for more casual settings.

The timeless appeal of navy and charcoal lies in their ability to complement a wide range of skin tones and hair colors, making them a universally flattering choice.

Additionally, these colors exude a sense of understated elegance, aligning perfectly with the Old Money aesthetic.

Look for sales or consider reputable brands like Suitsupply or J.Crew Factory for affordable options that don’t compromise quality.

2. White or Pale Blue Dress Shirt

White Dress Shirt Charles Tyrwhitt
White Dress Shirt – Image courtesy: Charles Tyrwhitt

A crisp dress shirt is a must-have for any gentleman.

Choose a high-quality cotton fabric that feels comfortable against your skin.

A white dress shirt is the most versatile option, as a blank canvas for various tie and suit combinations.

A light blue shirt offers a slightly more relaxed feel while maintaining a polished appearance.

Look for brands like Charles Tyrwhitt or Brooks Brothers for reasonably priced, well-made shirts.

These brands offer a balance of quality construction and affordability, making them ideal for the budget-conscious gentleman.

3. Dark Denim Straight-Cut Jeans

Levi's Dark Denim Straight-Cut Jeans
Dark Denim Straight-Cut Jeans – Image courtesy: Levi’s

A pair of dark wash, straight-cut jeans is a timeless classic that can be dressed up or down.

The dark wash adds a touch of sophistication, making them suitable for casual and semi-formal occasions.

The straight-cut silhouette is universally flattering, accommodating various body types.

Avoid ripped or distressed styles for a more polished look.

Brands like Levi’s or Lee offer affordable options with a classic fit and a heritage that aligns with the Old Money aesthetic.

4. Polo Shirts

Polo Shirts Uniqlo
Polo Shirts – Image courtesy: Uniqlo

Polo shirts are a versatile addition to any wardrobe, bridging the gap between casual and formal wear. Invest in black, white, and pastel-colored polos for maximum versatility.

The classic colors offer a clean and refined look, while pastel shades like pink, blue, or green can add a touch of personality without being overly flashy.

Choose polos made from high-quality cotton for comfort and durability.

Brands like Lacoste or Ralph Lauren’s Polo line offer classic polos that exude timeless style, while more affordable options can be found at retailers like Uniqlo or Express.

5. V-Neck Jumper

V-Neck Jumper Everlane
V-Neck Jumper – Image courtesy: Everlane

A V-neck jumper in a dark blue, grey, or brown shade adds a layer of sophistication to your outfit. Wear it over a dress shirt with jeans or chinos for a polished yet relaxed look.

The V-neckline visually elongates the torso and complements the lines of a collared shirt.

Opt for a fine-gauge cashmere or merino wool blend for warmth and comfort without bulk.

Brands like Uniqlo or Everlane offer affordable options with quality materials.

In contrast, brands like John Smedley or Pringle of Scotland offer luxurious cashmere options for those seeking to invest in a higher-end piece.

6. Chino Pants

Chino Pants Dockers
Chino Pants – Image courtesy: Dockers

Chinos are a versatile alternative to jeans, offering a more refined look while maintaining comfort and ease of movement.

They can be dressed up with a blazer and dress shirt or down with a polo shirt or sweater.

Opt for khaki, navy, or grey chinos for maximum versatility.

These neutral colors pair well with various tops and shoes, making them a practical choice for any wardrobe.

Brands like Dockers or Bonobos offer affordable chinos in various fits and colors, while brands like Incotex or Polo Ralph Lauren offer premium options with superior craftsmanship.

7. Black or Brown Leather Dress Shoes

Black Leather Brogue Dress Shoes Cole Haan
Black Leather Brogue Dress Shoes – Image courtesy: Cole Haan

A pair of well-maintained dress shoes is essential for any gentleman’s wardrobe.

Choose classic styles like oxfords or brogues in black or brown leather.

The timeless design of these shoes ensures they will never go out of style, and the high-quality leather will age gracefully with proper care.

Invest in quality leather care products to keep your shoes looking their best.

Brands like Allen Edmonds or Loake offer Goodyear welted shoes built to last, while more affordable options can be found at retailers like Clarks or Cole Haan.

8. White Crew-Neck T-Shirt

White Crew-Neck T-Shirt Everlane
White Crew-Neck T-Shirt – Image courtesy: Everlane

A simple white T-shirt is a wardrobe staple that can be dressed up or down.

Choose a high-quality cotton T-shirt that fits well and feels comfortable against your skin.

The clean, minimalist design of a white T-shirt makes it a versatile layering piece or a standalone item for casual wear.

Brands like Uniqlo or Everlane offer affordable options with soft, breathable fabrics, while brands like Sunspel or James Perse offer premium, high-quality, and comfortable T-shirts.

9. Khaki Shorts

Khaki Shorts J.Crew
Khaki Shorts – Image courtesy: J.Crew

Khaki shorts are a summer essential, offering a comfortable and stylish option for warm weather. Pair them with a polo or dress shirt and loafers for a preppy, polished look.

Opt for shorts made from breathable cotton or linen fabrics for comfort in warm weather.

The neutral color of khaki complements a variety of tops and shoes, making it a versatile choice for summer attire.

Brands like J.Crew or Gap offer classic khaki shorts at affordable prices, while brands like Orlebar Brown or Vilebrequin offer premium options with superior craftsmanship and unique designs.

10. Brown Leather Loafers

Brown Leather Penny Loafers Clarks
Brown Leather Penny Loafers – Image courtesy: Clarks

Loafers are versatile shoes that can be dressed up or down, making them a valuable addition to any wardrobe.

Choose a pair in brown leather for a classic look that complements various outfits.

Penny or tassel loafers are timeless styles that never go out of fashion.

The slip-on design offers convenience and a relaxed yet refined aesthetic.

Brands like G.H. Bass & Co., Sebago, or Clarks offer quality loafers at reasonable prices, while brands like Gucci or Tod’s offer luxury options for those seeking the finest craftsmanship.

11. Cotton or Linen Button-Down Shirt

Linen Button-Down Shirt Brooks Brothers
Linen Button-Down Shirt – Image courtesy: Brooks Brothers

A lightweight, breathable button-down shirt in cotton or linen is a summer essential for the Old Money wardrobe. Opt for classic colors like white, light blue, or pastel shades.

The button-down collar adds a touch of formality, while the lightweight fabric ensures comfort in warm weather.

Brands like Brooks Brothers or J.Crew offer affordable options with classic designs, while brands like Eton or Turnbull & Asser offer premium shirts with exceptional quality and craftsmanship.

12. Classic Outerwear

waxed cotton Barbour jacket
Waxed Cotton Jacket – Image courtesy: Barbour

A timeless piece of outerwear is essential for completing the Old Money look.

Depending on your climate and personal preference, consider a waxed cotton Barbour jacket for a rugged yet refined look, a classic trench coat for a sophisticated and versatile option, or a wool overcoat for colder months.

These outerwear pieces are investment pieces that will last for years and can be dressed up or down depending on the occasion.


Focusing on these 12 essential wardrobe staples can help you build a versatile and stylish Old Money wardrobe without breaking the bank.

Remember, the key is to invest in quality pieces that you love, which will last for years.

Creativity and attention to detail allow you to achieve a timeless look that exudes class and sophistication.

With over twenty years of front-row fashion and styling events, collabs with haute-couture houses, and a PhD in Luxury Fashion, Laurenti is an expert in crafting personalized looks that depict old-money sophistication.

With years of expertise in high-end fashion collabs and a PhD in Sustainable Fashion, Ru specializes in curating eco-luxe wardrobes for the modern gentleman seeking understated refinement.

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