Dressing Well, Rule #1 – Get a Great Tailor

A dog is not always a man’s best friend. If you want to look your best – whether it’s formal, business, casual – the first thing you must do is get a great tailor.

Over time a man’s relationship with his tailor takes on a transcendental quality. He comes to know intuitively the minute details that will make any piece of clothing look better on you … in a half-inch here, out a smidge there. It may sound trite but trust me it matters.

I am not talking about just having bespoke suits or coats made, though nothing fits like a custom-tailored suit and every man should have at least one – I have six, a couple dating back almost 20 years. I am talking about almost every piece of clothing you’ll wear – blazers, sportscoats, suits, trousers, overcoats – will fit and look better with a few tweaks.

An additional but important benefit to well-fitted clothes is not just that they look better, but they feel better on you, and you’ll feel better wearing them. When you feel good in your clothes, you look better yourself. It’s the antithesis of a vicious circle, it’s a wonderful circle, and other people will notice.

A few tips in making the right selection once you begin your search for a tailor.

First, find someone who you click with on a conversational level because your relationship will solidify faster.

Second, do not be bullied or coerced into “it’s in fashion now” decisions; a good tailor understands that every man is different and some, like me, are not interested in what’s hot today, rather what has stylish longevity.

Last, look for someone who takes clear pride in their work and enjoys seeing their clients looking good, not just seeing their money; in this regard you’ll know instinctively when you have the right person.

One other terrific value of having the skills of an experienced tailor at your service, is it can save you money. Secure in the knowledge you can have any reasonably fitting piece of clothing altered to fit perfectly, you can afford to shop with greater flexibility. So, you can, and should, start shopping for higher quality clothing that may not fit perfect but is on sale; online values are readily available and you just need the general fit right. Your tailor can make it virtually perfect and your combined investment can frequently be less than a poorly-fitting off-the-rack piece.

Finding a great tailor is an investment in time, your time, but it’s an investment that will pay dividends for years to come. And once you’ve found the right one for you, I assure you that you’ll start looking better, feeling better, and the compliments will roll in.

While my closet does have some bespoke suits that cost more than many men would spend, there is nothing else you see that I paid anything near retail for and with the deft assistance of a good tailor, everything fits, and looks, incredibly well.


In closing, if you’re located or travel within an hour of Harrisburg, PA then I have an unabashed recommendation for you … go see Dale Kaplan. He’s been doing what he does for forty years and possesses all the traits of a truly great tailor. Trust me you will never regret it and you will be better dressed.

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