It’s been a long time since I had to wear a suit to work, and hopefully it’s something that I will never have to experience again. I actually enjoy wearing suits but the ritual of getting yourself ‘suit ready’ every morning, when you’re half asleep and starving and angry that you’re awake before the sun is up, just sucks. Many guys are not as lucky as me and don’t live in the great grey pacific northwest where suit wearing is mostly reserved for the middle aged salesmen at Jos. A. Bank and Men’s Warehouse. But more and more I’m hearing that even in New York City, suits are slowly fading from the norm. They’re still occasionally needed but not necessarily an everyday requirement.
So let’s say that you live in the northeast and work in one of these places that encourages but does not mandate suit wearing, what are you wearing to work? If you know what’s good for you you’re still probably in slacks and a button down at minimum, maybe even a sport coat. If you’re lucky, maybe you can get away with a nice pair of jeans. Let’s also say that you’re not waist deep in cash and don’t have a walk in closet just for your dress clothes. It would behoove you to have a pair of shoes or two that you can wear to work anytime, walk around in comfortably, and in a pinch, wear with a suit. It would also be nice if these shoes were comfortable enough to wear out after work into the wee hours of the night when your friends decide to drag you to one more bar even though you haven’t showered in 16 hours and smell like feet and butt just to follow some “cute” girls. Such shoes do exist but let me say right off the bat that there will be no loafers in this post. I hate loafers. Even the most expensive hand-made Italian leather loafers still look like sexed up slippers to me. And who wears slippers? Old retired men wear slippers, in between wearing sandals with a lot of straps, and golf shoes. No slippers/loafers. They’re the male equivalent of ballerina flats, but instead of making you look classy, you look you may need a video tutorial on the “bunny ears method“.
Anyway…For me, and this is probably a factor of having both worn a lot of shitty or ill-sized shoes and having played sports, but comfort will ALWAYS trump appearance (still, NO LOAFERS!) so I would try on a sample or two of each the brands featured below before buying anything. There is nothing worse than springing for a pair of shoes that look awesome but cut off the circulation to your toes. This can happen. Don’t lose your toes. Try stuff on before you buy it.
Cole Haan Lenox Hill Cap Oxford – Classic black wingtips. I generally love Cole Haan – I’ve had a pair of almost these exact shoes for the last 10 years, and probably have worn them 400 times. They’re still comfortable and do not look their age, and as a result I support all things Cole Haan.
Cole Haan Colton Winter Wingtip – These are a little more fun with the brown sole and stitching. I’m probably too conservative to wear this pair with a suit but I’ve seen it done and it works. Once again Cole Haan equates to comfort and quality.
Allen Edmonds Neumok Oxford – I’m not sure if these are the exact pair but when I went home to NJ this past summer for my friend John’s wedding, several of his friends, and John himself, were rocking these shoes in various colors. A classic shoe design with an updated color palette and a ton of detailed stitching.
Beckett Simonon Dunne Derby – John also introduced me to this brand and after a bit of reading it seems that they’re a great bang for their buck. These shoes are 1/3 the price of Cole Haan but offer almost the same quality appearance. I’m a shoe snob and a leather snob and these are the first pair of “cheap” shoes of this type I’ve ever liked.
Beckett Simonon Bailey Chukka Boot – I’ll be honest, I’m not sold on Chukkas as a style, but supposedly these are pretty comfortable and at that price point, they’re certainly worth a try.
Clarks Desert London in Black Suede – Clarks are known for their comfort and affordable prices. I’ve tried on similar shoes of theirs in the past and they do certainly feel comfy. They’re also extremely light – a benefit of having a composite sole vs. a wooden one. Overall this is a pretty standard design in an attractive suede package.