3 Things You Shouldn’t Get Tailored

Prevailing wisdom is that you should get almost everything tailored that you can. And I agree with that. The key word in that sentence, for the purpose of this article, is “almost”. Because there are a few things that, I believe, you should NOT get tailored.

Hopefully, this article will help save you some time and money.

A good tailor is a blessing. I started seriously getting into menswear when my wife and I were living in upstate New York. There was a small chain of local dry cleaners in the area and the largest location had a tailor whom I ended up visiting frequently.

Wendy was an absolute wizard and the more I went, the better and better my pieces looked since she knew my preferences.

That was some years ago and I have just recently found another tailor who is on par with Wendy.

My point with all this is that I fully understand the importance of having a relationship with a tailor. That being said, there is a danger in taking tailoring too far.

If you buy a suit, or a sport coat, or a pair of trousers, then yes, obviously take them to get tailored. That goes without saying. You’re supposed to get them tailored. They are made so that they can be tailored easily.

But there are a handful of items that, if you get them tailored, risk pushing you over the tailoring line from doing something sensible to help you look your best to being fussy and fastidious.

Here are three things you should not get tailored.

Keep in mind as you read: This advice does not apply to those individuals with unusual body types. If you’re six-foot-ten or something else outside the spectrum of what is considered normal then I understand that you’ll probably need to get everything tailored or bespoke. There’s nothing wrong with that. This article is more for people who have been bitten by the “tailoring bug” and risk taking it too far.

This article also does not apply to those who may have lost a bit of weight and are eager to get some of their pieces tailored so they can enjoy and feel confident in their wardrobe. If this is you, then congratulations, and by all means tailor all the things! You’ve earned it!

#1 – Jeans

Remember that scene in The Office where Pam makes fun of Michael for having his favorite jeans dry-cleaned?

That’s how you will look if you get your jeans tailored.

Jeans are casual workwear. They aren’t supposed to fit perfectly. They’re the pants you wear when you don’t need to look perfect. They’re for getting down and dirty. They’re for getting things done. The imperfection and utility are what make them so attractive. They don’t need a perfect break or just the right amount of drape.

Also, we men are at an advantage over women when it comes to buying clothes. Our pants actually come with measurements so we can get pretty reliably close to our actual size upon purchase. That means that there really shouldn’t be a reason why your jeans would be way too big in the waist or long in the leg which would necessitate a trip to the tailor.

If your jeans are a touch big in the waist, wash them on hot and wear a belt. If they’re too long in the leg, cuff them. If the sizing is way off, just return them and get a different size. There really is no need to get them tailored.

Tailored jeans will make you look like a big dork. And “nice jeans” are for much younger men who still feel uncomfortable “dressing up”. If you need a nice casual option for pants, go with a pair of chinos.

#2 – Ties

Tie blade length is something that causes much consternation among men. For most of us, the wide end and the thin end usually fall at roughly the same length when tied in a common knot like a four-in-hand. There are some variables that might alter that outcome, like the thickness of the tie’s material or the rise of the trousers, but most of us just tie our tie so the blades are in the same general vicinity and continue with our day.

There are some, though, who can’t handle the uncertainty of how their tie blades will fall and insist on getting their ties tailored so they are exactly the length they want.

But is it really worth it?

How much did the tie cost in the first place? Fifty bucks? A hundred bucks at most? How much does it cost to get it tailored? Even if it’s just $25, that’s still 25% to 50% of the original cost of the item.

Also, ties never knot in the exact same place, which is why you can tie a tie several times before you get the ends the proper length. If you get a tie tailored, you’re still going to run into that exact same problem.

Your tie will never be exactly the right length. That is ok. Check out pictures of many of the stylish men of yesteryear. The lengths of their tie blades are all over the place. They still looked damn good.

#3 – Oxford cloth button-down shirts (OCBDs)

Since dress codes have gradually relaxed over time, we tend to think of the OCBD as a “dress shirt”, since it isn’t a t-shirt or polo shirt.

But it really can be styled quite casually, as you are probably all well-aware.

This means that the OCBD should be treated similarly to the jeans in entry number one. To put a finer point on it: the appeal of an OCBD is that it isn’t perfect. It’s a little rumpled. It’s a little frayed. It might be a bit blousy. These are why an OCBD looks great under a tweed jacket or a chunky sweater. Or open at the beach.

An OCBD doesn’t have to be perfect in the way that the stark white, French-cuff, spread collar poplin shirt you wear to the office does.

The go-anywhere-do-anything, utilitarian-but-not-boring nature of the OCBD is what makes it so handsome. Just like jeans.

And just like jeans, we can get these shirts in exact neck and sleeve sizes within a multitude of fits. There isn’t any reason why we should have such an ill-fitting OCBD that we need to have it tailored.

The only caveat to that is if you received one as a gift. If the size if off considerably and you really can’t wear it without getting it nipped and tucked here and there, then go ahead and get it tailored.

It really comes down to the fact that none of this stuff should be “spot on”. This isn’t your dinner jacket or your white-tie-and-tails. These items look best when there is a little imperfection to them.

The final point I’d like to make on the subject is to also be careful that you aren’t reflexively getting things tailored even if it’s not needed.

For those of us who enjoy classic menswear, it’s almost a thoughtless action to take a jacket or suit to a tailor a little while after purchase. Usually, this makes sense. We are used to things not fitting properly off the rack.

But there are times when something DOES fit perfectly off the rack! In those cases it can feel a little weird to wear something out of the house that hasn’t been altered by a tailor in some way. I experienced this with a jacket from Aran Sweater Market that my wife bought for me a couple years ago. I put it on and did the mental assessment of what I would have my tailor adjust. But I couldn’t find anything. The sleeves were the perfect length, there was just the right amount of room in the body, and the collar didn’t budge from my neck.

How convenient! I could wear it straight away without waiting to get it back from the tailor!

So, don’t sweat it if you can’t readily find anything that needs to be tweaked when you buy a garment that usually needs tailoring. Consider it lucky and make sure you purchase from that company in the future since you know their stuff fits you well.

So, if you’re thinking about getting your jeans, tie, or OCBD tailored, remember the sage words of Dr. Ian Malcolm (just replace the mention of “scientists” with “dudes who like menswear”) …