Welcome to the 2nd installment of Menswear Mondays…where my brother Silas again puts me to shame.  Seriously, he even poses better than me.

I’ll let him take it from here…

Today I want to talk about one aspect of the basics. Since it is the one aspect I lack, as well as the one aspect that can really drain your wallet, I want to get it out of the way. 

I’m talking about shoes, zapatos, schuhe, chaussures…whatever your language may be, the fact cannot be escaped that a nice shoes are not cheap. Some other items you can get away with skimping on cost (cue my eclectic list of various shirt brands), but shoes are not one of them if we want to do this right. 

There are a few generic styles of shoes every man should own: 

The Driving Moc – The driving [moccasin] is, in my humble opinion, the most casual shoe you can wear outside of a tennis shoe. “What about docksiders?” – Ok, those are pretty casual too however I think they are a bit over played. Pictured here is a Cole Haan Driving Moccasin

These happen to have laces but many of them are simply flat front or have a penny loafer type strip of leather over the mid foot. These shoes are great in the spring/summer sans socks and just as good in the fall with some fancy argyle socks. You can wear them with jeans, chinos, or casual dress pants.

The Penny Loafer –  The penny loafer is a step up in class from the driving moc however with some confidence you can still wear them pretty casually.


I personally don’t advocate wearing cuffed jeans with penny loafers in real life, but I liked the picture to display the versatility.  I would wear penny loafers with or without socks with chinos and dress pants. I would probably avoid black myself – not a big fan of black anything, except tuxedos.
The Fall Boot – Boots are a personal favorite of mine. There are too many great boot options out there: Redwing, LL Bean, Sebago, Wolverine, Clarks, Timberlands (not “tims” specifically) to name a few.

Pictured is a broken in Alden 405 Redwing boot. If you know your movie history, you may recognize these boots. They are the type of boot that Indiana Jones wore in his movies. I didn’t choose them because I want to be Indiana Jones (anymore), I chose them because they are top of the line quality and with the right care, will out last their owners. These would look great with a dark wash jean or chinos.
The ideas I have listed are pretty expensive. I would be lying if I said that I have or will have all of these anytime soon. But, my hope is that you have gained a few more ideas on what to wear besides tennis shoes. 

[Editor’s note – anything is better than tennis shoes. Except flip flops. Those are usually much worse.] 

Pictured:
Ralph Lauren Navy quarter-zip sweater
Chaps blue stripe OCBD [Oxford Cloth Button Down – I had to look that up]
Kohl’s Nantucket Red chinos
Good Will tassel loafers