Men's Clothing Forums banner
1 - 20 of 51 Posts

·
Registered
Joined
·
331 Posts
In general, I wouldn't advise it. But if your boss is a complete slob, you may have no choice. And of course, lot depends on your line of work, and your boss's attitude toward the way you dress.

I've had bosses who have appreciated my style, and I've had one boss -- he fancied himself something of a "populist" -- who would routinely give me crap for dressing well. To him, any kid walking around in something above Men's Wearhouse was spoiled. I don't think my nice clothes seriously offended him or anything (especially given the fact that he was loaded and wore super-expensive bespoke everything). But they signaled to him, somehow, that I was high-maintenance or from a wealthy background. That's not exactly the case, but it's the image I was evidently conveying. Mainly, I think he was just hyper-sensitive to clothing; I don't think most people would be that extreme. But you never know.

The best advice I can give it to try to take the temperature of the situation before making your move. Start on the conservative side (i.e., do not dress nicer than your boss at the beginning), then try to get a feel for things. When in doubt, don't overdo it.

In general, one of the occupational hazards of being smartly attired is that you'll always run into people who are rubbed the wrong way by it. They're few and far between, but they are out there, and sooner or later you'll encounter them. I think the type is far more common in the U.S. than abroad, though.
 

·
Registered
Joined
·
784 Posts
A long time ago in the dark ages of the mid-eighties, I had my one and only corporate office experience. I was the art and advertising director of a short-line railroad that had high public and industry visibility.

At the time the line was under the management of a small group of guys that bought the line through an LBO. One of the partners, who wanted his name plastered on one of the locomotives, and had his business card read (name) "Owner," thought he was well dressed in lower end suits, and cheap shoes. He made a point of displaying his frugal fashion sense to people. I would wear Brooks Brothers suits, with bespoke shirts and, of course, stiff collars. He never said anything directly on the matter but would make some snide remarks such as, "You don't need to wear expensive clothes to work," or "You think you're blah blah blah." He made my life miserable, as he did with a lot of people, and would never aprove a raise for me. They went bankrupt a year after I left.
 

·
Banned
Joined
·
16,023 Posts
It's funny this topic comes up, because I was voted, "Most likely to get fired by outdressing their boss," by my friends in high school. Of course, that category never made it in the yearbook, but we were too cool to be popular enough.
 

·
Registered
Joined
·
758 Posts
I suggest slowly evolving into it -- don't show up day one wearing bespoke everything.

Start with a nice but simple OTR suit, shirt and tie. Over a period of time move up the sartorial ladder one step at a time.

Most people will notice one of two things: A) he is wearing a suit and tie, or 2) he is not wearing a suit and tie. Few people can recognize the difference between OK OTR and top-of-the-line bespoke.

If you gradually lead them by the hand you will win them over. After a while, they will just come to understand that's his style and how he dresses (or, your embezzeling money from the company and spending it on fancy clothes).

AD
 

·
Connoisseur
Joined
·
5,988 Posts
First of all I think one needs to define "dressing better than the boss". For example, are you dressing better than the boss within the parameters of the accepted corporate culture or are you dressing better than everyone including the boss to the point that your appearance no longer fits within the said corporate structure.

Most workplaces have some sort of dress code whether it is formally stated or simply accepted informally by general consensus. The issue then becomes not one of whether or not you are dressing "better" than the boss, but are you dressing so different from the boss (and everyone else for that matter) that you become an oddity. This holds true whether everyone is wearing jeans and you have on a suit and tie or whether everyone has on suits and ties while you are wearing jeans. It isn't that your dress is better or worse, but that it's different.

If, on the other hand by dressing better you simply mean that you are wearing bespoke suits vs. the boss' JC Penney suits along with accessories like French cuff shirts and pocket squares while the boss is wearing $5 ties or even no tie, I think it becomes a non-issue. Heck, I doubt that most bosses would even notice. Remember, as a general rule people who aren't sartorial enthusiasts don't tend to notice the more subtle things that an enthusiast would notice.

Remember the story of the Emperor who's kingdom had a poison well. As the people drank from the well they went crazy. Finally all of the people were crazy with only the Emperor retaining his sanity. At this point the people saw how different the Emperor was and concluded that he was crazy and should be overthrown. The Emperor quickly went to the well and drank the water, after which he went crazy like the others. The people saw this and rejoiced because the Emperor had regained his sanity was now like them again.

As long as you stick within the general parameters of the corporate culture I doubt that there will be a problem with dressing better; but get too far outside of those parameters, either better or worse, and the people will think you are crazy and you might need to go drink from the well. :icon_smile:

Cruiser
 

·
Banned
Joined
·
16,023 Posts
I don't know... it can be subconscious when it comes to dressing in bespoke or otherwise well-fitting clothing with cuff showing and perfect break. Some of my friends don't know a wing collar from wingtip shoes, but they've seen pictures of guys in bespoke as "dressed better than a lot of men now."
 

·
Registered
Joined
·
286 Posts
I'm a software engineer currently but am doing my MBA and am going to move to marketing when the opportunity presents itself. My boss is a slob. I can't even begin to list all of his issues, but just a few:
-wearing his 1860-era Civil War reenactment officer's coat when it's cold out
-denim shirt with denim pants
-black chinos, white socks, brown belt (or none), black Reeboks, yellow polo (go Steelers!)

He doesn't like the marketing group and the other day I had a knit tie under a sweater vest and he made the comment as soon as I walked in a meeting that, "You even dress like 'Bob Smith'", who is the head of marketing. I just muttered something.

I don't worry about it, he doesn't have enough clout to do anything and we get along well, he just has no tact.
 

·
Registered
Joined
·
2,689 Posts
It depends on the boss; from my experience, most like it because it shows you are making an effort. However, do not over-do-it, especially if you are in a junior position.

My old boss only wore a suit if there was a management meeting and I told he should wear a suit everyday (even without the tie) but he said he could not be bothered. His normal shirt rotation included full-sleeve and half-sleeve shirts :crazy:

I did have a contract with the marketing department of a publishing company. Wearing a casual shirt was being smart, I wore jeans, chinos and casual trousers; although Friday was a smart day because people normally went out after work.
 

·
Super Moderator
Joined
·
27,866 Posts
Once had a boss in the early '70's who had a daily uniform. It consisted of burgundy polyester bell-bottoms, a matching short sleeve shirt, a burgundy and white polyester tie, all topped off with white patent leather slip-ons and a matching belt. He would routinely counsel me to drop my glen checks and chalk stripes so I could "get the girls."
 

·
Registered
Joined
·
4,773 Posts
Once had a boss in the early '70's who had a daily uniform. It consisted of burgundy polyester bell-bottoms, a matching short sleeve shirt, a burgundy and white polyester tie, all topped off with white patent leather slip-ons and a matching belt. He would routinely counsel me to drop my glen checks and chalk stripes so I could "get the girls."
Sounds like...all burgundy...

Burgundy is a good color. If matches to a lot of things and I like hunter/burgundy in the fall, but this is over the top...
 

·
Registered
Joined
·
331 Posts
Once had a boss in the early '70's who had a daily uniform. It consisted of burgundy polyester bell-bottoms, a matching short sleeve shirt, a burgundy and white polyester tie, all topped off with white patent leather slip-ons and a matching belt. He would routinely counsel me to drop my glen checks and chalk stripes so I could "get the girls."
I bet his apartment contained many leather-bound books and smelled of rich mahogany.
 

·
Registered
Joined
·
219 Posts
Go in with eyes wide open, and when in Rome... do like the Romans. If 2 button blue suits & striped ties are the norm, then wearing something in that style, but of better quality, fit and color/pattern coordination would probably go unnoticed. They will just know you always look good, and may not really understand why. But if you wear charcoal chalk stripe double breasted suits, french cuff shirts, etc... Mr. Big will focus on your clothes, and might view you as a show off, wanna-be bigshot, etc. Or, if your clothes are truly outstanding, and not just outside the culture norm, the boss may feel intimidated and view you as a threat. These thoughts come from my own personal experience. If you care about the job, your grooming standards and style should blend in with the environment.
 

·
Registered
Joined
·
53 Posts
I'd be happier if my boss dressed in burgundy flares now days. As it is, myself and the Marketing director regularly kick his ass with our sartorial kung fu, mixing bespoke with choice retro stylings.

The depressing thing is that not only does he not notice and not care - he's gets more than double the salary that we do !
 

·
Registered
Joined
·
21 Posts
Dear Sean,

There are some people that just don't care about fashion and details, but are very harsh on people that do like it. If your boss is insecure, you can be in trouble. Of course he will not tell you that he doesn't like you because of that issue. But be aware that he can feel a little bothered with you.

Try to pay attention when he talks to you. If he keeps looking at your clothes, its a bad signal. If he don't even looks or make a comment about your clothes, you're safe.
 
1 - 20 of 51 Posts
This is an older thread, you may not receive a response, and could be reviving an old thread. Please consider creating a new thread.
Top