Tailor-Made – How A Good Tailor Can Make You Look Like A Million (VIDEO)

Old-school tailor doing a fitting.

There’s something different about a man who has a tailored wardrobe. A good tailor’s alterations can make your Good Will bargain look like a million bucks. Photo of the ever-stylin’ Sean Connery being fitted for a James Bond film from A Suitable Wardrobe.

As your men’s fashion advisor, I suggest you find a tailor who can do custom alterations. Find one if you can.

When you decide to get serious about looking good, sometimes buying things off the rack isn’t enough. Nor is it necessarily a good idea to spend $200-$500 on a stupid shirt the way magazines like GQ and Esquire exhort you to do. No wonder guys don’t usually care about this stuff. Who wants to be treated like a cash cow by multimillionaire fashion designers? I sure as Hell don’t. I’ve been fortunate enough to find good tailors a couple of times in succession, and you should make the effort too.

Three reasons to find a good tailor.

  • A good tailor can make a $15 suit or blazer you found at Goodwill look like something on which you spent $1000. OK, maybe $500.
  • A good tailor can instruct you on things to look for when you go on shirt- and pants-buying excursions.
  • A good tailor will tell you whether an article of clothing is made of good fabric and is made well, and is worth altering.

How to find a good tailor.

You’re better off finding someone who’s been in your community for a long time, if possible. This is getting more and more difficult, particularly in Silicon Valley. But recent arrivals can also work very well. With such people you do need to know exactly what you want, and be willing to make that clear. You’re the boss, and it’s your money you’re spending. Start any tailor off with one or two pieces that aren’t part of your most strategic rotation, so you can get a fix on how effective that tailor is before committing to that expensive suit alteration. One clever thing to do is to bring in a photo of the look you’re shooting for along with the clothes you want altered to match, and to let them know that THAT is what you want.

Old-school tailoring is becoming a lost art.

Old-school tailoring is becoming a lost art. There are fewer and fewer old-school tailors around, and many dry cleaners who used to feature alterations don’t do a very good job or only do simple ones on very limited hours. There used to be SCHOOLS for tailoring! If you go looking, you need to be pretty touchy about what you’ll settle for, because many of the “new school” of recent-immigrant tailors in the area will charge more and will sometimes do a poor job, and simply not tell you whether a given job is worth the effort or not. I have gotten burned on this a couple of times, including a recent case where a simple case of hemming a pair of pants turned into a butcher’s job.

Ties with custom alterations by a tailor.

A few ties from Good Will with custom alterations by our local tailor.

I’ve toyed with the idea of buying a sewing machine and doing some of my own alterations. Fortunately, I found someone else in San Jose who fulfills all of the things I’ve told you about here. I have brought all of my suits to her, most of my sport coats, and am now working my way through many of my dress shirts. Eventually, and not too long from now, I am going to run out of things to give her. She’s been around here for over 40 years in the same place, and handled all the local cops’ and firefighters’ alterations for time out of mind. Now nearing the end of her career, I feel very fortunate to be able to simply walk over to her old storefront, have her measure out each alteration (sticky pins!) and come back in a week or two. It seems trivial, but this is an increasingly rare and valuable thing, and getting much harder to find. Times are changing.

Here’s how a good tailor can make a big difference.

Tailoring your clothes can make a significant impact on your style and your self-confidence. As Jose Zuniga from Teaching Men’s Fashion explains, “When your fit’s not right, it looks like you’re wearing borrowed clothes. Like it isn’t for your body, making you look shorter, or fatter, or even sloppy.”

Watch Zuniga’s before and after video to see what a big difference a good tailor can make:


It’s an unusual feeling to routinely wear custom-tailored clothes. There’s something different about a man who has a tailored wardrobe. It makes you feel that you have something no one else really has, as shallow as that sounds. But it’s also the truth. It’s also motivational. Who wants to suddenly put on 20-30 pounds and have to start buying new threads after you’ve gone through the time and expense to have your clothes tailored? Keep hitting the gym and watching what you eat, and this will never be a problem.

About the author

Richard Grace is a technical writer and long-time denizen of Silicon Valley. He thinks men's style in Silicon Valley could use a bit of improvement. For the latest Groovy Man Stuff, friend him on facebook, "Like" his Groovy Man Stuff page, follow him on Twitter, or plus him on Google+. And since this is Silicon Valley, Richard also has a Linked In profile.