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Essential Dress Shoes for a Perfect Old Money Look – Gent’s Guide

Old Money shoes have stood the test of time and continue to be a staple in the wardrobes of gentlemen with refined taste.

With thirty years of experience helping young gents master the art of timeless style, my knowledge of men’s footwear that defines the Old Money aesthetic is on point.

In this article, we’ll introduce you to the essential dress shoes every man should own in his curated Old Money style wardrobe.

These shoe styles, especially when made by iconic brands, are a must to showcase the sophistication and confidence of the Old Money look.

Main Takeaways
Oxfords, loafers, brogues, and monks are must-wear dress shoes for Old Money outfits.
Black, brown, and oxblood are the best colors for timeless Old Money looks.
Invest in heritage shoe brands renowned for their timeless designs.
Different dress shoes suit different occasions – always wear the correct dress shoes.
Details such as leather finishes and subtle embellishments are important.
Avoid Chukka and Desert boots if you want to look Old Money.

Seven Types of Old Money Dress Shoes for Men

1. Oxford Shoes

Old Money style Oxford dress shoes

Oxford shoes are the epitome of elegance and formality, and no Old Money shoe collection is complete without this quintessential style.

Characterized by a closed lacing system, where the eyelet tabs are sewn underneath the vamp, Oxfords are versatile and can be worn with suits or dressed down with chinos.

Black and dark brown colors pair effortlessly with various outfits.

John Lobb, Edward Green

Dos and Don’ts
  • Do pair it with suits for formal occasions
  • Don’t wear it with shorts or overly casual outfits

2. Derby Shoes

Smart casual Old Money style derby shoes
Derby Shoes

With an open lacing system, the Derby shoe offers a slightly more casual alternative to the traditional Oxford.

Also known as Bluchers, this shoe style has an open lacing system, with eyelet tabs sewn on top of the vamp.

Derby shoes are less formal than Oxfords, hence an excellent choice for less formal events or business casual settings.

For a refined look, choose a pair in a versatile color like dark brown or burgundy.

Crockett & Jones, Alden

Dos and Don’ts
  • Do wear it with business casual attire or smart casual outfits
  • Don’t pair it with formal suits

3. Loafers

Business casual Old Money style Loafers
Loafers

Loafers are slip-on shoes in various styles, each with unique features.

The shoe’s preppy roots explain its ability to balance casual and formal, making it a go-to choice for business casual ensembles and relaxed social gatherings.

Apart from the penny and horse-bit loafers, several other shoe styles are great at creating that classic Old Money charm.

3.1 Penny Loafers

Highly versatile, penny loafers can be dressed up or down.

G.H. Bass, Rancourt & Co.

Dos and Don’ts
  • Do wear it with chinos or jeans for a smart casual look
  • Don’t pair it with formal suits

3.2 Horsebit Loafers

A signature style of the Italian luxury brand Gucci, featuring a metallic horsebit ornament on the vamp.

Gucci, Salvatore Ferragamo

Dos and Don’ts
  • Do wear it with tailored trousers or suits for a sophisticated look
  • Don’t pair it with athletic wear or overly casual outfits

3.3 Tassel Loafers

This style of loafers has decorative tassels on the vamp that add a touch of flair to any outfit.

Alden, Allen Edmonds

Dos and Don’ts
  • Do wear it with dress slacks or chinos for a polished look
  • Don’t pair it with shorts or athletic wear

3.4 Kiltie Loafers

Featuring a unique, eye-catching fringed leather tongue that covers the vamp.

Alden, Tricker’s

Dos and Don’ts
  • Do wear it with casual suits or smart casual attire
  • Don’t pair it with formal suits

3.5 Belgian Loafers

A minimalist slip-on style with a small bow on the vamp, known for extra comfort and a favorite among the Preppy set.

Baudoin & Lange, Rubinacci

Dos and Don’ts
  • Do wear it with chinos or linen trousers for a laid-back, sophisticated look
  • Don’t pair it with athletic wear or overly casual outfits

4. Monk Strap Shoes

Old Money Style Dress Monk Strap Shoes

Monk straps are characterized by a buckle closure instead of laces and are a stylish alternative to traditional lace-ups.

Mon monk shoes are available in single-buckle and double-buckle variations, adding a unique flair to your Old Money look.

For a sophisticated appearance, opt for a pair in rich, dark leather.

4.1 Single Monk Straps

Sleek and streamlined with one buckle.

Carmina, Santoni

Dos and Don’ts
  • Do wear it with suits or dress slacks for a modern, stylish look
  • Don’t pair it with shorts or overly casual outfits

4.2 Double Monk Straps

More intricate design with two buckles.

Crockett & Jones, Gaziano & Girling

Dos and Don’ts
  • Do wear it with suits or tailored trousers for a fashion-forward look
  • Don’t pair it with athletic wear or overly casual outfits

5. Brogue Shoes

Business casual Old Money style Brogues shoes
Brogues

Brogues are characterized by intricate perforations and wingtip designs and add visual interest to your classic shoe collection.

Ideal for showcasing your keen eye for detail and appreciation for artisanal craftsmanship, choose a pair in rich, burnished leather to elevate your sartorial game and make a subtle statement.

Brogues come in various styles:

5.1 Full Brogues (Wingtips)

Pointed toe cap with wing-like extensions and broguing along the seams.

Church’s, Grenson

Dos and Don’ts
  • Do wear it with suits or business casual attire for a classic look
  • Don’t pair it with shorts or athletic wear

5.2 Semi-Brogues

Straight toe cap with broguing along the seams and on the toe cap.

Tricker’s, Loake

Dos and Don’ts
  • Do wear it with suits, dress slacks, or chinos for a versatile look
  • Don’t pair it with overly casual outfits

5.3 Quarter Brogues

Broguing only along the seams, with no decoration on the toe cap.

Cheaney, Barker

Dos and Don’ts
  • Do wear it with suits or dress slacks for a subtly detailed look
  • Don’t pair it with shorts or athletic wear

5.4 Longwing Brogues

Pointed toe cap with wings extending around the shoe’s sides, meeting at the heel.

Alden. Allen Edmonds

Dos and Don’ts
  • Do wear it with suits, dress slacks, or chinos for a bold, distinctive look
  • Don’t pair it with shorts or overly casual outfits

6. Dress Boots

Old Money style dress boots

Dress boots are a stylish alternative to traditional dress shoes and a practical option for colder months.

Chelsea and lace-up ankle boots are the most suitable for an old-money look.

6.1 Chelsea Boots

Ankle-high boots with elastic side panels, easy to put on and off.

R.M. Williams, Carmina

Dos and Don’ts
  • Do wear it with suits, dress slacks, or jeans for a sleek, modern look
  • Don’t pair it with shorts or athletic wear

6.2 Lace-up Ankle Boots

A more traditional style, offering a secure fit and a classic appearance.

Crockett & Jones, Edward Green

Dos and Don’ts
  • Do wear it with suits, dress slacks, or chinos for a sophisticated look
  • Don’t pair it with shorts or overly casual outfits

7. Opera Pumps

Old Money style Opera pumps for men

Opera pumps, made of patent leather and characterized by a bow on the vamp, are the most formal men’s shoes.

As a traditional formal shoe, opera pumps in patent leather are ideal for black-tie events and galas.

Gieves & Hawkes, Shipton & Heneage

Dos and Don’ts
  • Do wear it with formal evening wear, such as tuxedos or tailcoats
  • Don’t pair it with business or casual attire

Brogueing and Toe Styles

Brogueing is the art of personalizing classic shoes to showcase the artisan’s craftsmanship level and add visual interest to your dress shoes.

Full brogues (wingtips), semi-brogues, and quarter brogues are all highly customized and suitable options for an Old Money wardrobe.

However, remember that the more extensive the brogueing, the less formal the shoe becomes.

The ideal dress shoes for an Old Money look must have classic toe styles, such as plain, cap, and apron toes.

Avoid square or pointy toes, as they can appear trendy and detract from the refined look you’re aiming for.

Old Money Shoe Brands

Traditional English shoemakers like Church’s, Crockett & Jones, and Edward Green set the standard for the Old Money style.

These heritage brands embody timeless elegance with their exceptional craftsmanship and classic designs.

Italian shoemakers like Santoni and Testoni are renowned for their exceptional craftsmanship and innovative designs.

These beautifully crafted shoes are synonymous with luxury and refinement, making them an excellent addition to your Old Money wardrobe while embracing the Italian art of sprezzatura.

Invest in bespoke or made-to-measure dress shoes from renowned brands like John Lobb and Gaziano & Girling for the ultimate luxury and personalization.

These one-of-a-kind shoes are a testament to your commitment to sartorial excellence and personal expression.

Old Money Shoe Mastery with The VOU

Gentlemen, crafting an Old Money look is all about paying attention to the finer details, and your choice of dress shoes plays a pivotal role.

The VOU’s team of stylists for successful gentlemen is dedicated to helping you understand the world of classic footwear, ensuring that you always step out in style.

Whether you’re attending a formal gala, a business meeting, or a relaxed social gathering, we’ll guide you in selecting the perfect pair of dress shoes to complement your ensemble.

From the timeless elegance of Oxfords to the laid-back sophistication of loafers, we’ll help you build a shoe collection that reflects your unique personality and aspirations.

Find your unique style with The VOU’s fashion style analysis today and embark on a journey of sartorial discovery.

Until next time, keep putting your best foot forward, and let your dress shoes reflect your refined taste and appreciation for the finer things in life.

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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