10 Exquisite Dress Shoes for the Discerning Gentleman

The discerning gentleman knows that the right pair of shoes can make or break your outfit. When dressing up, whether for a formal outing or a business engagement, it is important to dress like a gentleman, from head to foot. Here are our picks for some of the best dress shoes:

1.     Salvatore Ferragamo – Carmelo. $895
2.     Fratelli Rossetti – Dark Brown Leather Wingtip. $630
3.     Tod’s – Calzoleria Wingtip Blucker. $665
4.     Salvatore Ferragamo – Faraone. $595
5.     Crockett & Jones – Westbourne. $595
6.     Harris – Medallion Cap Toe Balmoral. $595
7.     Crockett & Jones – Hallam. $570
8.     Ralph Lauren Black Label – Denham. $550.
9.     Barneys New York – Cap Toe Balmoral. $445
10.  Franceschetti – Plain Toe Chukka. $445

If spending upwards of $400 on a pair of shoes isn’t your cup of tea, check out brands such as Rockport, Florsheim, Kenneth Cole and Johnston and Murphy. They do a fine job mimicking the styles of the top designers at a fraction of the price.

Before you shell out your hard earned money on the best shoes you’ll ever own, you want to make sure you’re buying the right pair. If you are not sure which shoes to buy, or how to match them with your outfit, consider these rules to live by when it comes to choosing shoes:

1.     Any metal bits on your outfit – from the belt buckle to the suspenders, the blazer buttons, cufflinks, and shoes – should be matching. (Although the metal on your watch does not have to match, it is preferable.)
2.     In formal settings the only color shoes acceptable are: black, brown, and oxblood (burgundy).
3.     Black shoes may be worn with a navy suit or pants.
4.     The color of your shoes and your belt should match.
5.     When wearing a suit, loafers should not be worn. In dressy settings, shoes should be tied, not slipped on.
6.     Stick with classic leather for dress shoes – no alligator, ostrich, or any other bizarre hides.
7.     Avoid shoes with tassels and other outlandish embellishments.

190cookie-check10 Exquisite Dress Shoes for the Discerning Gentleman

Join the Conversation


  1. An interesting discussion is worth comment. I think that you should write more on this topic, it might not be a taboo subject but generally people are not enough to speak on such topics. To the next. Cheers

  2. So tieing of said shoes – when I google the list above – most of the shoes have the laces all running horizontal – but a few had the “traditional” criss cross – not sure I have seen the horizontal lace before – whats the story there?

      1. So no cardinal rules are being broken or I’m not showing my lack of eye for detail sticking with the criss cross ?
        Thanks – Ben

  3. So What’s the story with that SERIOUSLY UGLY pair of shoes in the picture above? Of ALL the shoe pics available online you had to use that nasty pic? LOL!

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