Shoes for Every Occasion

One pair of shoes rarely suits every occasion. This guide looks at the styles that form a useful foundation for a man’s wardrobe, how formal each one feels and which colours are easiest to wear with different outfits.

There are countless shoe styles today. Some have a long history; others appeared more recently.  

The right shoes depend on your wardrobe and the settings you dress for, including work. Even so, a few versatile styles can form a practical starting point.

Three pairs are a useful starting point: one formal pair and two less formal options. Together they give you more ways to dress for different occasions without filling the shoe rack.

Start with a formal pair.

Formal shoes: Oxfords

Oxfords come in a plain style or with a toe cap: an extra piece of leather across the toe. Black Oxfords suit the most formal occasions, including an evening suit or tuxedo.
If you do not wear black, dark brown pairs well with navy, grey and beige outfits.

Related article: Six tips for choosing the right belt.

Less formal derby shoes

Derby shoes have open lacing and work well with less formal outfits. Some have decorative perforations known as broguing. Brown shades, particularly lighter brown or tan, are easy to combine with many clothes. Blue or dark green can also work, though they may be less versatile.

Double monk-strap shoes

Double monk-strap shoes fasten with two buckles and offer another less formal option. Colours range from familiar browns to oxblood, a deep reddish brown. Choose a shade that works with the clothes you already own.

Loafers

Loafers slip on without laces or buckles. They offer an elegant but relaxed option for a casual evening or a Sunday afternoon with friends. They also work well with a bare-ankle summer look.

Chelsea boots

Chelsea boots are a versatile ankle-high option. Wear them with jeans and a light shirt for a relaxed, smart outfit; they are practical for travel too.

Need advice on looking after leather shoes? Read our shoe-care guide.

To recap

A practical three-pair collection might include black Oxfords for formal occasions, brown Derbies and a third style to suit your taste: monk straps, loafers or Chelsea boots. Dark brown and tan are versatile choices. Oxblood adds another option if it fits your wardrobe. Before choosing a brighter colour such as red or blue, consider what you would wear it with.

You now have a starting point for choosing your next pair of shoes. Whatever style you prefer, pay attention to fit, construction and how often you are likely to wear it.

Cavalier also offers hand-sewn leather shoes. Explore our shoes and belts. Our style consultants can help you choose a pair.