First, let me provide some personal background in clothing selection. I grew up a country boy around farms and I often wore overalls or cargo pants purely for their practical utility. You could keep tools, knives, and/or flashlights on you that you needed as you went about your day. In my even younger years, you'd often find my brother and I in either Sears Toughskins jeans or hiking pants and shorts. Those hiking pants, or "camper" pants as we called them, had open-pockets and snapped-pockets and zippered-pockets and loops, and even snaps to hold a key ring.
A lot of people don't realize that tactical pants started out as utilitarian pants for mountain climbers originally designed and sold by Royal Robbins. In fact, the 5.11 pants get their name from the the rating system for the difficulty of climbs by mountaineers... the most difficult of which was rated at 5.11 at the time. The idea of being prepared for daily tasks lent itself to clothing being selected more for practical needs as opposed to fashion.
In my professional life, while I did work as a police officer for a number of years a couple of decades ago, I have been a photographer and designer for many years. The utility and practical aspect of "cargo" style pants for a commercial and advertising photographer doing studio and location work can never be underestimated. I've misplaced enough lens caps over the years to affirm this.
Long before people even knew what a "shoot-me-first" vest was, I was wearing a photographer's vest on a regular basis. I personally find that carry items in pants pockets tends to be less cumbersome and intrusive than vest pockets, so you rarely find me wearing the vest the last few years. The pants are still very handy in my current day job as I teach full-time and move about a university campus between computer labs and photography studios, but many others find practicality in "tactical" pants. I've seen university maintenance personnel and an electrician in 5.11s and one copier technician who wears "paramedic/EMT" pants to hold their tools.
But... but... if you wear tactical pants everyone will know you have a gun and you'll never be a "grey man". In my experience, not really. First of all, there are so many people wearing tactical pants whether the carry concealed or not, I don't think they really don't stand out any more... especially to those outside the "gun culture". Second, I've found that the large majority of the general population don't even know what "tactical" pants are and don't even pay attention to them.
A lot of people don't seem to look side to side, let alone below eye or chest level as they go through life. The few aware, concealed carry "sheep-dog-types" out there may notice, but I'm not usually concerned with them being a threat. While a criminal might think "Mr. Tactical Pants has a gun I could steal."... I'd imagine a lot criminals sizing me up are deterred overall by my dress and manor... and will look for an easier target. Most criminals are not stupid... they, like most predatory animals, look for the weakest, easiest target in the herd.
Two years ago, I tried a little visual experiment to gauge the visual observance of my students who are in a visual design field. I taught for an hour while wearing black 5.11s, a black sweater vest, and a maroon button-down shirt and my black, dress walking shoes. I placed a paper face down by each student and asked them not to turn it over until I left the room, then I left the room. They turned the paper over and I asked simple visual questions like "What was the background color on the Powerpoint presentation I went through?", "What color pants was I wearing?". "What color shirt was I wearing", "Was there anything special about the pants I was wearing?"
After going to my office and changing into plain black slacks, the black sweater vest and a blue button-down shirt, I returned about five minutes later. One student exclaimed to another student, "See, I told you his shirt was blue!" Only one student had noted something special about the pants... being that I always carried a Point-n-Shoot Canon camera in the one leg pocket, but he couldn't recall if I wore those pants that day since I was standing there in slacks. Only four of seventeen could accurately and confidently recall the background color of the Powerpoint presentation that I used for over an hour of lecture and Adobe Creative Suite demonstrations. Now this is not a truly definitive scientific study, but it shows that being a "grey man" is not that difficult in our tuned out society.
As far as being the "grey man", my wife, daughter, and I try to live a very visually bland life. We have plain vehicles without bumper stickers that declare, "Kill them all and let God sort them out" or "Driver only carries $20 worth of ammo". Anytime someone looks at your vehicle and jokingly thinks or says, "he's compensating for something", you're not blending in. Additionally, our daily clothing choices are not flamboyant or attention-getting. I think you can dress nice and professional without looking like a complete tactical ninja or wearing look-at-me styles and clothing choices.
I think going "grey" as much as possible is a good thing for most people's safety. Our home, barns, and property are extraordinarily average in appearance. We have a shooting range behind our larger barn and most people who don't live near by and know us have no idea it is even there as they drive by. The most noticeable thing on our property are the "Miller Security System" signs on the home and barns signalling we have an alarm system in place and the two large dogs and canine-accessories like water dishes and chew toys that say, "Don't mess with our home."
My wife and daughter dress nicely, but they don't dress or carry purses that scream "look at me" or move them to the top of the "target" choices for criminals looking to score the most in a purse grab or sexual assault. (No gals, I'm not blaming any victims for their assaults, but if you don't think the way you dress and act matters... you're not living in reality.)
We don't flash cash around when we discreetly get our wallets out to pay for something. We don't carry smart phones with brightly colored or decorated cases. We definitely don't text or plug our ears with earbuds while walking around... if you're going to put yourself in Condition White with technological visual and auditory impairment, then do it at home in a physically secure environment, not in a high visibility area... and especially not if you're advertising what you have might be worth taking.
So being a grey man can be done in different ways and at different levels, but I ask you for your thoughts... is it possible to be... A "grey man" in tactical pants?