Complete Guide to Men’s Shoes and Boots

Discover Crockett & Jones: elegance, comfort, and refined style. Oxford, Derby, loafer, or boot—find the perfect pair for every occasion.

Complete Guide to Men’s Shoes and Boots
  by Guy Douville

Choosing the Right Men’s Dress Shoes: A Complete Guide

Picking the right dress shoe for men can feel complicated. Why are some pairs more formal while others appear casual? It all comes down to the style and model. Many men don’t know the difference between an Oxford, Derby, loafer, or ankle boot.

This detailed guide will help you understand the distinctions and select the perfect pair for every occasion—work, weddings, weekends, or special events.

Men’s Dress Shoes

Oxford (Richelieu)
The Oxford is the most formal men’s shoe.

  • Laces are sewn directly onto the vamp.

  • One-cut, seamless versions are ideal for weddings, galas, or black-tie events.

  • Decorated styles, like broguing, are elegant but slightly more casual.

  • Example: Crockett & Jones Alex

Derby
A classic style, less formal than the Oxford.

  • Laces are attached to the quarters, not the vamp, providing more room for wider feet.

  • Suitable with suits, sport coats, or smart-casual outfits.

  • Example: Crockett & Jones Grasmere or Hardwick

Loafer
A laceless shoe combining practicality with elegance.

  • Available in both formal and casual designs, depending on leather and style.

  • Perfect for a refined office look or weekend wear.

  • Example: Crockett & Jones Boston

Monk Strap
Between a Derby and a loafer, this shoe offers a unique and stylish twist.

Men’s Boots

Chukka
A low, timeless boot with roots in the British Army.

  • Balances comfort and elegance.

  • Available in smooth or suede leather, dressy or casual.

  • Example: Crockett & Jones Molton and Upton

Brogue Boot
A high, stylish boot built like a Derby.

Balmoral Boot
A rare, sophisticated boot constructed like an Oxford.

  • More challenging to put on, but a symbol of unique elegance.

Chelsea Boot
Defined by elastic side panels.

  • Easy to wear, comfortable, and timeless.

  • A male style icon made famous by the Beatles.

  • Essential in any stylish wardrobe.

  • Example: Crockett & Jones Chelsea 8

Practical Tips for Choosing Shoes

  • Formal or casual? Match your shoes to the occasion.

  • Prioritize comfort: A new shoe may feel stiff initially but should never be painful. Ensure correct sizing, including width.

  • Invest in classics: Well-maintained classic shoes can last a lifetime.

  • Care for your shoes: Shoe trees, polishing, and cleaning prolong lifespan.

  • Vary your styles: Alternate between low shoes and boots to diversify your looks. Avoid wearing the same pair two days in a row—let them rest at least 24 hours.

In short, a man’s wardrobe is full of styles and variations. Visit our store to discover the perfect pair, feel the leather, and try the model that will complete your elegance.

  by Guy Douville