Dress shoes are a staple in the wardrobes of gentlemen with refined taste.
In this article, we’ll introduce you to the only seven types of dress shoes prefect for the Old Money style you should have in your wardrobe.
The dress shoe style, especially when made by iconic brands, must be styled with Old Money outfits to showcase sophistication, success, confidence, and wealth.
All Dress Shoe Types
1. Oxford Shoes
Oxford shoes are the epitome of elegance and formality, and no shoe collection is complete without this quintessential style.
Characterised by a closed lacing system, where the eyelet tabs are sewn underneath the vamp, Oxfords are versatile and can be worn with double-breasted suits or dressed down with chinos.
Oxford shoes in black and dark brown pair with most colour outfits but ideally, you’ll match them according to your seasonal colour palette.
Recommended Brands
John Lobb, Edward Green
Dos and Don’ts
- Pair Oxfords with suits for formal occasions
- Never wear Oxfords with shorts or gym outfits
2. 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.
Derby shoes in dark brown or burgundy are great choices, matching with a wide range of suit colours.
Recommended Brands
Crockett & Jones, Alden
Dos and Don’ts
- Wear Derby shoes with business casual attire or smart casual outfits
- Never wear them with formal suits
3. 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.
Recommended Brands
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 horse bit ornament on the vamp.
Recommended Brands
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.
Recommended Brands
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.
Recommended Brands
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 favourite among the Preppy set.
Recommended Brands
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
Monk straps are characterised 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.
Recommended Brands
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.
Recommended Brands
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
Brogues are characterised 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.
Recommended Brands
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.
Recommended Brands
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.
Recommended Brands
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.
Recommended Brands
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
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.
Recommended Brands
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.
Recommended Brands
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
Opera pumps, made of patent leather and characterised 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.
Recommended Brands
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 personalising 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 customised.
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.
Best Dress Shoe Brands for a Classic Look
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 personalisation.
These one-of-a-kind shoes are a testament to your commitment to sartorial excellence and personal expression.
| Key Takeaways |
|---|
| Oxfords, loafers, brogues, and monks are some of the best dress shoes. |
| Black, brown, and oxblood are the best colours – but check your seasonal colour first. |
| Buy dress shoes from heritage brands. |
| 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. |
Styling Beyond Dress Shoes
Knowing the main type of dress shoes and considering having them in your wardrobe is just a small step towards dressing like a confident and successful gentleman.
Perfect men’s styling starts with your unique body type and colour palette and only then, with the occasion, location, season, and time of the day – and this is a men’s styling secret that only expert image consultants know.
And if you want to learn, we’re here to help; start by knowing your body type and unique colour palette so you can select clothes for your body shape in colours that match your skin, eyes, and hair.
You must also know which fashion brands to shop from and, more importantly, how to style these garments, footwear, and accessories to create a look of subtle luxury and success.
After learning to choose fashion from heritage fashion brands according to your body shape and colour palette, you’ll have to master styling by occasion, location, season, and even time of day.
If you feel overwhelmed, worry no more – we’re here to help you in three easy and free steps:
1. Find Your Body Type
Different garments flatter different physiques, so knowing your body type is the first step in dressing like a confident man – free body shape quiz for men.
Once you know your unique body type, take the second free quiz to discover your unique colour palette.
2. Find Your Unique Color 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 type and unique colour palette, so 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, multiple outfit ideas, the most relevant fashion brands for your unique look, and much more.
4. Professional Image Consultancy with The VOU
Last but not least is mastering how to style according to occasion, location, season, and time of the day; this is where our professional styling services for men, created by our expert image consultants and fashion stylists, come in.
Our paid styling packages are the most comprehensive and detailed on the market. Each is backed up by expert stylists who will guide you step by step in creating a personal wardrobe that communicates affluence, elegance, and endless accomplishments.
Remember, owning luxury clothes isn’t enough; to look stylish, confident, and successful, you must know your body type and colour palette and how to style according to the 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.