How To Dress…And Why

Brooks Brothers shirt

There are numerous magazines, websites, books, and blogs that offer up advice on how to dress. Very few of them tell you why to dress. In The Old Money Book, I do.

The first reason you dress is because very few people look good naked, and, secondly, we have laws against taking that kind of liberty in public. (Wink, nod.)

Seriously, we dress to communicate. And we communicate so much to others before we ever say a word…by the way we dress.  We tell them our aspirations, our occupation, our income level, our educational level, our family background, and most importantly, our values.

Let’s set aside the knee-jerk reaction of “I don’t care what other people think. I dress for myself.” Very few of us have that confidence, self-awareness, or freedom. Most of us are required to dress for work. Most of us dress well for an important event, like a first date, or the first time you meet his or her parents. We’re human. We care what other people think.

Some events, like funerals, require somber and reserved attire in order to be considered appropriately dressed. The job interview often requires a navy blue, grey or black suit for men or women.  When you conform your dress to accommodate the event, you are communicating that the event is more important than your own sartorial preferences. You might prefer your favorite T-shirt and a pair of sweatpants, but you’re not wearing them to your brother’s graduation ceremony.

(If you dress however you please, whenever you please, without regard for the circumstances and you are very financially independent, you are called an eccentric. When you do this and you are not financially independent, you are called an idiot.  And by the way, eccentrics don’t do what they do for public consumption: it’s just the way they are.)

OMGs (Old Money Guys and Old Money Gals) dress appropriately. They don’t need attention, and certainly don’t want the kind of attention one gets from dressing to get attention. They don’t dress to communicate how much money they want other people to think they have. Many people probably wouldn’t notice how they were dressed, which is exactly the point.

Old Money dresses so the focus (as opposed to attention) falls on them (not their clothes) when they interact with others.

So download a copy of The Old Money Book and read the chapter on Attire. You’ll have an entirely new perspective on how to dress, and why to dress.

Thanks. – BGT

2 thoughts on “How To Dress…And Why

  1. Ok, serious question. How in the world should an adult man in his 30s dress? It seems to me that the hipster doofus try-hard has ruined mens fashion and made it impossible for the normal work-a-day male to dress nice! What to do? Thanks for the advice and help.

    1. Hi Jay, thank you for the question. Your frustration is shared by several gentlemen I know. My advice is threefold. First, define what you need for work. Is that a suit? Business casual? Or are most of your clothing needs for weekends and personal time? Second, lean toward the classics. You don’t have to dress preppy, but a pair of khakis, grey slacks, or jeans, and a nice white or blue shirt have been a go-to look for men for the last 75 years. Throw in a blue blazer and you’re ready for almost any event. Third, consider a trip to your nearest Brooks Brothers store or visit their online store. Obviously, they have traditional clothing, but they’ve also expanded their brand and offer items that are more contemporary. There’s also LL Bean, which I recent discuss in a post on this blog. Finally, you might consider buying a copy of The Old Money Book, which is available on Amazon. You can download it for 2.99. If you don’t have access to Kindle or Nook, just send me an email at I’ll be happy to forward you a hard copy of the contents at no charge, via US mail. Hope this has been helpful. Thanks again. – BGT

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