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"I remember that guy. He was wearing the green double breasted suit and he had a tie pin that kept falling off."
You never want to be remembered for what you wore in a sales meeting.
About 14 years ago, a client of mine joined a large and well known real estate company as CFO. Shortly after starting he was given $1,200 by the company and told to go buy a suit. He was told not to bring any of the money back but to spend it all on the suit. He was told the suit was to be worn when he met with banks.
It made sense to me then and it still does. By dressing employees, my friend's company took "cheap suit" anxiety out of meetings with people who had huge sums of cash to give them. Doubtful any of us will work for a company as wise and as generous but there's a valuable lesson here. If your employer won't invest in your selling appearance - then you must.
Figure $900 to $1,600 for a budget. Solid navy or gray to start with. If you're new to this, I recommend a worsted gray. In a pinch, you can wear the gray trousers with a blazer or sport coat. If you already have gray then it must be solid navy. When the navy trousers wear out replace the horn buttons with brass blazer buttons. A trick I learned from the cheapest Scotsman I know.
25 years ago the sack suit from J. Press was popular. Today, it's unique to the point of being fashionable. Still, it's an option and very close to the bottom of the budget. It's also excellent camouflage if you're packing an extra 15 or 20 pounds. But understand this...Nobody's gonna say, "Nice suit, Jim." because, like a good haircut, nobody will notice it. This is what we want when we're selling.
25 years ago, Brooks Brothers gave me a credit card and an employee discount. My first purchase was three suits. All Brooksgate 3 piece. Solid navy, Navy pinstripe and gray pinstripe. I'd still have them if I was a 40 Reg. They did see me through a ton of interviews. The FBI, where I failed the psychological exam twice. The DEA, where they failed my psychological exam once. The Director's Guild (East & West), where I failed the AD test both times. Doyle Dane and Bernbach, where I failed the, "Where did you go to college" test. And 20th Century Fox, where I failed the, "I don't know what I'm doing here" test. I never did test well.
If I did get the DDB job, I would've made a bee line for Paul Stuart. Sitting near the top of the budget is a beautiful navy suit with side vents and a low two button stance. Very flattering on shorter men. No ticket pocket or other bells and whistles. Just a simple Samuelsohn made suit. I was told it was their most popular model and who can argue with that.
It's impossible not to mention Brooks Brothers. Back in 1992, I worked for Bill Bartholomay. Chairman of the Atlanta Braves, Chicago Parks Commissioner and owner of Puerto Rico. Bill asked the Straight Arrow I worked with if anyone still shopped at Brooks Brothers. Mr B was a card. That's Bill up there in the bad Mani gabardine with the ugly, but ever popular mid west, Countess Mara tie. The picture's from M Magazine in April of '91 but Bill would look timeless if he had only worn a navy Golden Fleece chalk stripe. They're pushing $2,000 today but are frequently on sale which puts it within our budget.
A mentor told me the idea of thinking yourself "special" is like finding yourself on the very end of a tree branch. Like a black suit, you're far from the support of the trunk -- you're literally out on a limb all by yourself. There's great comfort in being one with the tree. These 'tree' suits will communicate nothing negative but, their quiet quality can put you on the buyer's short list. The rest is up to you...and your shoes.