Shoes for Fall

Let's talk about shoes.

The first nip of fall is in the air, and it is time to start taking our footwear a little more seriously. Time to say goodbye to the canvas sneakers, boat shoes and the flip flops. There are lots of ways to go and we are always looking for shoes and sneakers that have good balance, great style, and excellent value. For fall, we like leather and suede, usually brown, and the occasional dash of color. We also love quality and only seek (and wear) shoes that will feel great, look fantastic and are built to last. Shoes are a nice way for men to add some flair and sophistication to their wardrobe. Here are six faves that will take you through the fall, winter and beyond. These picks are classic and cool and will never go out of style.

Monk strap shoes have been seeing a revival of late that does not appear to be ending any time soon.  There are lots of gorgeous versions out there and Allen Edmonds offers superb quality and great value. Instantly add a bit of Italian sprezzatura to your look. 

Blundstones are simply an excellent boot.  Stylish, easy to wear and virtually indestructible.  I have had a pair for 12 years with no sign of failing.  I love this pair with the green stretcher for a bit of flair.  And I like to let my jeans get "caught" in the pull straps to show off the whole boot. 


The retro running shoe as day wear is a look that has been kicking around for a couple of seasons.  I resisted at first, but there is something about their proportion (a little height in the heel never hurts) and the fantastic color combinations that have given them a sophistication I have come to like.  The New Balance 574 is the best of the best and comes in many great styles and fabrics. 

The Alden Cordovan Long Wing Blucher is another great option.  I love the chunky proportions when balanced with a slimmer jean or suit pant and the built to last craftsmanship.  These are an investment but they will last a lifetime and never go out of style. For a sophisticated urban look, you can wear them with no socks and jeans or go old school classic with a suit and tie.  

Chippewa boots have been around for over 100 years.  If you are looking for a sturdy lace up work boot that is also attractive, versatile and can stand up to real work and real play, these are for you.  More great value and they are also built to last.  


I am a Clarks Desert Boot fanatic. I have been wearing them all my life. There are a lot of other fancy versions out there and feel free to overpay for them.  The classic, never out of style version, is Clarks.  I wear mine for a winter or two, beat them up good, and then pick a new pair.  At just over $100 you can't beat this for style and value.  This year I am picking the Desert Boot in Beeswax instead of my usual suede brown or blue.  I like to change the laces on these to one with a color (green, red, blue) to take them from basic to something special. 

I am always looking for a penny loafer that is classic but not so retro that it can't be sophisticated.  I love this Cole Haan version.  It comes in different colors, some more sedate but I love the version in blue.  I won't wear these every day but every once in a while to perk up the same old jeans and oxford shirt.