VI. Shoes


More than any other wardrobe classifications, shoes are where quality almost always will cost you less over time. And over that time, they will look better and feel better.

It has been our experience that the price point that returns value starts around $350."Investment Footwear"(our term for shoes that provide style, comfort and last upwards of 15 years if maintained properly) start around $500.

There are plenty of searchable articles about shoe care and how to identify quality, so we will jump directly to what shoes you should have in a “Fit Kit”. In order of descending formality: 

1. An Oxford is a shoe with laces, such as our Alden cap toe or medallion. Our choice is dark brown or cordovan shade. An argument for black is that in a plain toe style, they could be worn “Black Tie”, but our feeling is black does not offer the same range of formality and color coordination. 

2. A Derby has an open lace system (see illustration) and is less formal than an Oxford. Versatility reigns supreme here; wear with a suit during the week, wear with jeans and khakis over the weekend.

3. A slip-on like our tassel loafer can also be worn quite dressy, but pairs nicely with sporty attire.

4. Chukka boots, particularly in suede, offer a decidedly “English Country” look. 

5. Our favorite casual slip-on (loafer) is the Beefroll Penny Loafer. It doesn’t get any more uniquely American than this.

6. Our rule used to be if you’re wearing sneakers, then you should be running. But we are being won over by a dressy sort; usually done in leather with a rubber, more active-looking sole. We even see them being worn with suits.

7. Not necessary, but enjoyable options for men who correctly see shoes as an accessory:

Suede Bucks, tan in the Fall and Winter, white in the Summer.

Bit Loafer (Gucci style) Casual and elegant, particularly in a soft deerskin.

Single or Double Monk Strap. Just because. 

And, like all Fit Kit categories, the following rules apply:

Versatility. A shoe that “fits” a greater range of your work and casual week is better.

Make sure the fit is correct. An experienced salesman can be a great help – but bottom line, you are the guy in the shoes. Trust your instincts.

Buy fewer but buy better.

Take your time in building your shoe wardrobe. Develop and refine your style as you go along.


I. Navy Blazer

II. Dress Shirt

III. Wool Dress Trouser

IV. The Suit

V. Casual Trouser

VI. Shoes

VII. Knits & Sweaters

VIII. (Coming Soon)

IX. (Coming Soon)

X. (Coming Soon)

XII. (Coming Soon)

XII. (Coming Soon)