Today’s post is the story of the worst purchasing mistake I’ve ever made. To be honest, I don’t know if I learned a lesson that I already didn’t know. I hope, at the very least, the story of me and this dress shirt provides some additional insight for you.

To help put things in perspective, I haven’t purchased clothes (outside of one pair of jeans) in the last 2 years. I prefer to wear clothes until not even Good Will will accept them.

This story begins about one year ago today. I was sitting at work when I noticed an email come in from a luxury shirt tailor in Chicago. The email was addressed to me, Matt, and I was surprised since I have not given my information over to any such merchant.

The email was explaining how this particular tailor was having an, ‘appreciation month,’ for all employees at my particular Big4 accounting firm. Great! Who doesn’t love being appreciated, right?

The email went on to say I should come in for a free fitting AND a free dress shirt.

I thought this was too good to be true, so I called in to ask if I needed to buy a shirt to receive the free one. The man on the phone said, “Nope, it’s a free dress shirt.”

“What’s the catch?”

“No catch. We hope you enjoy the shirt and want to come back for more in the future.”

So, I booked my appointment.

Fast forward a few weeks and I’m enjoying free scotch inside a fancy looking shop. As my measurements for the dress shirt are being taken, I’m being asked for my address.

“Why do you need my address?”

“We need to make a profile so we can order your shirt.”

“Okay, the address is…”

The next part of our dialogue was more casual and the fitting was complete. As I submitted the final pieces of my order, the man helping me out asked for my credit card information…

“What? I thought this was a free shirt?”

“The shirt is 100% free, but we need your credit card to complete the profile.”

I took him at his word and the shirt was ordered. It turned out there was no catch, it was a free shirt.

End of the story.

“But, wait…”, you ask, “What about the $300 shirt?”

Oh yeah, so then…

The week after I had my fitting done and the shirt ordered, I received a call from another tailor.

They explained on the phone they wanted me in for a free fitting and they could even set me up for a free shirt.

Wow, this must be my lucky week…or so I thought at the time.

I walked into the fitting and the process was almost the same as I was greeted by a nice woman. Some small talk, measurements, a complimentary cocktail, and profile questions later. I provided my credit card because that’s what it takes to get the order completed. It was almost like the first tailor was playing the long game with this 2nd shop.

When it came time to place the order, I asked if the shirt was free. The person assisting me had no idea what I was told on the phone and started explained all the current deals they had going on.

“Okay, so the shirt is not free?”

“If you don’t like the shirt, we can always return it…”

“So if I order the shirt and don’t like it…?”

“You don’t need to keep the shirt, but I think it’ll be great on you, blah blah”

“Okay, sounds good to me.”

I had the order set up and I looked forward to having my 2nd free tailored shirt. I figured if I ever had some crazy occasion in the future where I would need a 3rd tailored shirt, then I would now have two different options to look back to.

When I got home that night I saw an email with my receipt and a charge to my credit card for $300. I hadn’t spent $300 on clothes over the last 2 years combined, so you can imagine my stomach dropped.

I immediately looked at the receipt and through the details. I saw $300 and non-refundable, so I called into customer service immediately.

Long story short, when I placed the order, the charge was made and there were no refunds. When the woman said I don’t need to keep the shirt, what she really meant was, you don’t need to keep THAT shirt. I can be refitted and opt for a different style or color of shirt, but still get charged for one shirt. It was essentially a store credit.

It’s been almost a year, and I still have the sinking feeling in my stomach for having purchased a $300 tailor made shirt.

The lesson I took away from ending up with a $300 dress shirt will hopefully save me a lot of money when it comes to buying a car or a house in the future: Patiently ask the right questions.

Have you made any purchasing decisions that you later regretted? Even worse, have you found yourself accidentally purchases hundreds of dollars of goods without even realizing it?

Master Distiller

P.S. I went back to posting on Tuesdays this week and I will stick to posting 3x/week. You can expect new posts this week on Thursday and Saturday mornings.

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