Retrofitting The Man – Part 1 | Shoes

This week begins CrabAppleNYC.com blogger Sam’s series on Retrofitting The Man – a five (or so) piece series that revolves around updating the wardrobe of a fashion-backwards guy, namely me, to something that is a bit more modern, hip and sophisticated.

Let’s get off on the right foot here – I truly appreciate what Sam is doing. I am – self-admittedly – style (he hates the word fashion) unconcious. I usually go to Old Navy or the Gap, find something that looks comfortable and not completely outlandish and then wear it until it’s dead. That needs to stop.

Given that Sam is a good friend and probably the most knowledgable guy I know on mens’ style, I asked him to help me pick out some ideas. I knew going in that Sam’s choices would push me beyond my comfort zone a little bit and I was prepared for that. What you’ll see over the next week or so are my responses to his daily posts where he takes a look at my current fashion faux pas and makes recommendations that will elevate me to a better look.

What Are Those Pieces Of Crap You’re Wearing?

Yesterday, in his first installment of Retrofitting the Man, Sam tackled the initial problem I went to him with – replacing my raggedy ‘daily driver’ shoes.

The first thing Sam did was lambaste my choice in footwear.

Fair enough – again, I never claimed to have any style sense. I’ve always worn this style of shoe. They are comfortable (seems to be a trend with my choice in clothes and shoes) and goes well with chinos or khakis (is there a difference? Wikipedia says there is, but I don’t always trust them) during the week and jeans on the weekend.

But, fair enough – like I said, I’m open to broadening my horizons.

Sam mentions that most mens’ style publications recommend three pairs of dress shoes for every man: a black cap toe, a brown brogue (isn’t a brogue what an Irishman talks with?) and a brown loafer. Admittedly, I had to look all of those styles up online. Surprise, the beat-to-snot things that I’m still wearing to work today aren’t anywhere to be found on those lists! Oh, and just so you know, the pair of blakc shoes I own are even older than the turd-monsters shown above. They just aren’t nearly as beat up as I don’t wear them a quarter as much.

The Brown Work Shoe

The brown work shoes Sam picked out are quite nice. Although, in the interest of full disclosure, my initial reaction was that they look a lot like something my father would wear when he goes to church (maybe that’s a good thing?). I liked the Florsheim Tremonts a bit more than the Sebagos. They looked a little more modern and not so “Dad-like” to me. They definitely look upscale compared to the style of shoe that I’m rocking now. I’m sure a change to a shoe like this would raise a few eyebrows with people around me but, again, is that a bad thing?

The Black Dress Shoe

As I mentioned, my black dress shoes are also beat to snot simply from years of use. The funny part is that they shine up pretty nice, but the construction is faulty at this point – a combination of a cheaper shoe and multiple years of use.

Again, Sam offers two options here that I like – a Rockport Ellingwood and a Florsheim Edgar.

Both seem rather simple and nice with the Rockport taking the slight edge in my preference. Perhaps it’s the slightly squarer nose, I’m not sure the reason why I like them a bit more.

An interesting note in this section. Sam states that my choice in black shoes “should be [my] go-to choice for any time [I] puts on a suit.”

It is true that I tend to veer towards my black shoes when I put on my suit. But, I also own a pair of Bostonian Wingtips in a dark maroon color that I love to wear. They look very much like the ones shown below. See, I’m not totally a brute.

The Casual Shoes

During our correspondence prior to this series, I had mentioned to Sam that my office is very informal on Fridays. I usually wear jeans and a button down (untucked) or a polo. My footwear for these days has either been my brown shoes or a pair of hiking boots that I recently purchased.

Sam’s recommendation was to drop the hiking boot and move into something more casual.

He gave a few otpions, none of which really struck my fancy. I’m a blue-collar kind of guy and, when I’m casual, I like to be casual. The hiking boots shown above are actually very commonplace in my workplace and I most likely will continue to wear them. If I don’t wear them, maybe I’ll step up and wear a pair of the brown shoes he recommended with my jeans.

And on a side note – and I mean no offense here Sam – I will never buy a pair of ‘workboots’ from Land’s End. Workboots are made by Wolverine or Caterpillar and intended to truly be used when working. Lands’ Ends boots just don’t seem like the kind of boot a contractor would use.

Belts and Socks

Sam’s last set of recommendations centered around belts and socks – both areas that I tend to neglect. I recently just bought a black belt. And the reason I bought a black belt is because the casual brown belt that I had since I was in college (yes, it was probably 10+ years old) finally cracked.

I still need to get a more casual brown belt if only because a black belt with brown shoes looks weird to me. I have a few belts in my collection however – a nice formal maroon one that goes well with the Bostonians I mentioned, the black one I just mentioned, a thinner black one for my suits and, my pride and joy, a studded black belt.

Don’t worry, the last one ONLY gets worn while snowboarding. Sam’s recommendation about a canvas belt has me thinking though. It might be the perfect addition to my collection for a more casual look.

Socks? Who really thinks about socks? I sure don’t. To be brutally honest, the last socks I bought were a big package of probably 4-6 pairs that runs for about $12 at CostCo. Yeah, I hate to admit it, but they do the trick and help the budget.

Some of Sam’s choices are very nice, but I honestly can’t see spending the same amount on one pair that I spend on 4-6; especially for something as trivial as socks.

Overall Impression

Overall, I really liked Sam’s suggestions.

The brown and black shoes are something I’m going to look into more. I’ll chronicle any purchases I make in a later post.

The casual shoes were interesting as well and may be something I look at down the road, however I think I’m OK with my current set-up at the moment.

The belts and socks recommendations very interesting, but in the end, I think all I need is a standard casual brown belt to round out my needs there.

I’m really looking forward to today’s post about pants. I’m losing some weight and need to buy some new work pants, so this post will definitely come in handy sooner than later.

Keep checking back for more reviews and leave us a comment about what you think!