How to Not Look Like a Complete Tool: Six Things to Avoid While Attempting to Dress Like a Professional, Pt. 2

Welcome back. If you're wearing a black suit, I'm sorry for your loss during this difficult time. Let me know who to send the flowers to. 

For part two of my six-part series (heads up: I have no idea what the other four parts will be), I've decided to write a brief post about one of the hidden dangers of menswear that can transform an otherwise decent outfit into a style disaster.

There is one dangerous item of menswear still floating around the ether of outlet stores and clearance racks that can change your entire ensemble from style-friendly to Boyz II Men stunt double reject. This, my friends and followers, is the dreaded square toed shoe. 

The square toed shoe, much like polio, is something most of us assume has been taken care of, cured and banished from this earth... until it rears its ugly head again. Square toed dress shoes have an unique ability to make anyone who dons them instantly look like some type of suit-wearing duck-billed platypus/human hybrid. It ain't pretty. 

Although they had their heyday in the 1620s at Plymouth Rock, square-toed shoes made a brief resurgence into popular attire during the 1990s. Worn by timeless mega A-list celebrities like Michael Bolton and Milli Vanilli, square-toed shoes are handy if you need flippers during your scuba adventure, not if you're trying to look like someone with a real job.

Wondering what shoes to rock with your suit rather than the square toed Stacy Adams shoes you found at payless for $8.99? Normally I require a consulting fee for my clients to know exactly which type of shoes to wear, but in this case I'll offer some free advice.

A rounded, natural toe shape gives a sleek silhouette and doesn't appear unnaturally large, small, square or pointed. An overly pointed shoe looks like you either work for Santa Claus or Roy Rogers, neither of which are in the Fortune 500. Save the pointy boots for the Wild West or the North Pole. 

A tasteful, natural toe shape discreetly highlights how much better of a person you are than everyone else around you. Pictured above, Allen Edmonds McCallister in Burgundy ($365)

How to Not Dress Like a Tool

Oh, hi!

Greetings! It's been a few, um, years. In honor of Easter weekend, I thought I would "resurrect" my blog back from the dead.

In honor of the (slowly) warming up climate, Easter weekend, and springtime in general, I thought I would help the style-illiterate men out there (AKA pretty much all of you except me) with several tips on how to easily avoid looking like a complete tool while trying to don professional attire.

How to Not Look Like a Complete Tool: Six Things to Avoid While Attempting to Dress Like a Professional

1.) BLACK SUITS

I remember the early days of attempting to dress in a "professional" manner. It was about two years ago when it hit me: I was on the cusp of a mediocre, possibly even lukewarm career (if I was lucky) in the legal profession, and my one charcoal-grey pinstriped suit in 38R with a 30" waist was the only armor I had to do battle with. A gift from my parents, it was actually a decent entry into the world of menswear. However, it would take about two days before my colleagues and adversaries would begin to notice that "THAT GUY WEARS THE SAME SUIT EVERY DAY!!" Having little to no idea about acceptable men's style, I turned to the world of Ebay.

I wanted my first suit to be neutral, something that goes with everything, something that nobody would notice if I wore it slightly more than I probably should. I thought about it, then I came across my brilliant revelation: BLACK! I would be a black suit!!! Black goes with everything! I found a Jos A Bank (AKA Jose Bank) suit on Ebay for 32 dollars, and although the color was not listed, the poor-quality photograph appeared to be a jet-black suit. 

Imagine my dismay when I eagerly tore open the package like a second grader on Christmas, ripping away packing tape and ripping the suit from its box like William Wallace's intestines on the chopping block, only to discover my surely-awesome black suit was.... NAVY BLUE!!!

Like a saddened Eddie Murphy finding out that the hooker he bought for the evening was a transvestite, I felt ashamed. Lied to. Disappointed. I felt like the world would just make more sense while donning a suit the color of Dick Cheney's soul. 

Boy was I wrong. 

There are PLENTY of occasions to wear a black suit. TONS! Here are a few examples:

1.) Your great-grandma Betty's funeral

2.) Your uncle Joe's funeral

3.) Your great-aunt Esther's funeral

4.) Your uncle Charles's funeral (yes, the same "uncle Charles" rapped about in "Crossroads" by Bone Thugs N Harmony circa 1996.) 

OR

5.) You're in the Secret Service. 

Get the point??

Black suits have the uncanny ability for any man who wears them to instantly look like the biggest jackass in the room. Depending on the room, that can be quite an accomplishment. 

When you wear a black suit, you say "hey, I give up."  Much like my prior self on Ebay, black is a seemingly-safe go-to color for those who don't know how to use color. However, indoors, black wool under artificial lighting has an uncanny ability to look both liver-failure yellow, seasick green, and choking-victim blue, all at the same time. It has a veneer of "formality" reserved for nighttime social events, but I say if formality is essential to the occasion, why not just go all out and rock a tux? Preferably a velvet pink tux with a shawl lapel. 

Thanks for reading Part One of my Six-Part series on how to not look like a complete jackass while donning professional attire. I hope you read it, and I hope you ditch that black double-breasted suit from 1987 that your Aunt Sally gave to you. Unless you plan on wearing it to her funeral.