Men’s Leather Dress Shoe Styles

There’s a saying that people judge or measure a man by his shoes (and it’s been that way for centuries).

Want to look smart and classy every time? You will need the help of luxury footwear.

Imagine getting $600 Italian Dress Shoes for less than $300…

That’s what makes Charlie’s Design a great brand. Our products are:

  • Comfortable to wear all day
  • Made of world-class, durable leather
  • Timeless in design

With Charlie’s Design shoes – guys like you and me can be AMAZINGLY stylish from head to toe.

This guide is an overview of men’s dress shoe formality meant to help you “generally” understand shoe types, the levels of dress, and what style shoe can be worn with what style clothing.

I admit it’s not perfect – if you have suggestions, email us. In later chapters we’ll tackle the issue of color matching and address specific styles like suede and cordovan.

Like most things in life, if you break it up into sections and apply a few guidelines it turns out to be pretty simple.

Balmoral (Bal)

The dressiest oxford men’s footwear selection. Sleek, refined, most often sold in black or brown but appropriate in any dark conservative color.
Style variations include plain, toe, cap toe, brogue, and whole cut. Appropriate for a suit, if casually styled works with sport jackets and odd trousers.
Do not combine with jeans or chinos.
Every man who owns a suit should own a pair of classic oxfords that are minimally styled. If you wear suits daily, you should rotate three pairs or more.


Less dressy than Bal oxfords, and identified by lacing  system sewn outside of shoe.

Well-dressed men know these can be worn with a suit, but are better with an odd jacket and trousers. They can be worn with jeans assuming they are casually styled.

Style variations include cap toe, wing tip, brogue, wide variation in materials like suede and mixed leathers.

Common variations are:

  • Saddle shoes
  • Derby’s
  • Spectators
  • Laced moccasins

A classic shoe that should serve as your 2nd or 3rd pair depending on needs – the more extreme the styling, the less versatile the shoe.

Men’s Loafers or Slip-ons

The least dressy choice, they are a product of comfort and convenience.

Only with a suit when traveling, they are at home with a casual odd jacket and trousers minus necktie. Can be worn with jeans or chinos as well.

Style variations are wide -usually the more delicate and closer resemblance to oxfords the dressier. Also, the greater the exposure of sock the less formal.

Common variations are:

• monk straps
• tassel loafers
• penny loafers
• unlaced moccasins.

Loafers are a traveler’s best friend – easy to slip on and off when going through airport security or when relaxing on the plane.
I recommend they be the 2nd pair a traveling man owns or the 3rd pair for a man who like to look sharp around town in jeans and button down shirt.

Next Blog will be about our high-quality and very affordable Bespoke Shoes and how you can get a pair or two …