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Choosing the Right Dress Shoes

In numerous previous posts I have stressed the need to choose the correct pair of shoes to accessorize your outfits when dressing formally. Today, lets break down some of the different options available to you and go over how to pick the right ones for your outfit!

2 Guidelines to Pairing the Right Shoes to Your Outfit:

  1. Do not wear brown shoes with a black suit. This is not okay.
  2. Understand the setting, for this will determine the type of shoes you choose.

Formal wear almost always means the classic dress shoe. There are multiple styles, such as the traditional Oxford shoe, the Monk strap, and Brogues. For those semi-formal or “casual Friday” days, your top choice is the Loafer.

The Oxford Shoe:

  • The Oxford Shoe is the perfect choice for that sharp, office look. This classic piece is a definite go-to, and never disappoints.
  • The style of this shoe consists of the narrow toe, slight detail around the shoe and thin laces.
  • When you are out buying a pair of Oxfords, keep in mind that they must be broken in, so initially, there may be slight discomfort. Ensure that your feet have enough room in the toe, you don’t want to be buying new shoes that cause so much pain!
  • I suggest wearing this with your everyday suit, completing the dapper look you’re looking to achieve.


The Monk Strap:

  • Personally, this style of shoe is my favourite. It works wonders for the formal and semi-formal look.
  • Monk Strap shoes are similar to the Oxfords, only with two buckles replacing the laces. They contain that suave quality with a fun twist that really pops in your outfit.
  • The best outfit to pair this type of shoe with would be three-quarter length trousers, a simple dress shirt and a tie/bow tie.
    Credit: @maxim_project


  • Brogues have a unique design, which is represented by the name of the shoe itself. Broguing is the holes and stitching design done around the shoe, giving it this distinct pattern that pops perfectly in any outfit.

    Credit: @orein2727
  • I suggest owning multiple colours in this style so you always have the right Brogue shoes to wear with any outfit.
  • This pairs well with the smart-style combo I wrote about in my previous blog. The classy aspect mixed with the expressive British culture will bring a new look to your everyday outfit.

    Credit: @orein2727
  • You are able to wear these shoes with the traditional trousers, or jeans for the semi-formal look.

The Loafer:

  • Loafers are a great choice for the summer casual look, especially when you pair them with a more formal outfit.

    Credit: @maxim_project
  • The cross between the formal outfit and the loafers (or slip-ons) creates a perfect balance, which still looks dapper and incredibly fashionable! The right outfit for this look is one that has a lot of funk, or character, to compliment the boldness in the loafer style.


  • A great example is pairing plaid trousers with a collared shirt and bow tie.
  • Alternatively, for the semi-formal look, pair them with short, European style trousers and a button down shirt.


Choosing the right pair of shoes is definitely a tricky task so hopefully this blog provides a little insight for you! The right idea is to be comfortable, which is especially important in your footwear. For more ideas on how to make the right combos, check out my Instagram @dysfunctionalwardrobe!

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