AITA for not being more specific with my tailor?

I (27m) have gone through a massive body transformation in the last 4 years. Like think 300 pounds, got the loose skin surgery, all of it. I’m very proud of how I look now, but I’m also not going to pretend I’ve lost all my insecurities.

I am going to be best man for my friend’s wedding and I’ve put a lot of pressure on myself to look good in my suit. I’m sick of always being seen as the fat friend and want people to see how I look now. So I decided to go to this old-school Italian tailor to get my precise measurements done. My brother recommended him.

When I’m there it’s one old guy and two younger guys working there (I think his nephews or sons? Anyway around my age). There are no other customers in the store at this point.

When I explain what I want done, he takes me to the back of the store and says to get undressed so he could get my measurements done. When I say back of the store I mean still out in the open, no privacy curtain or separation. I ask him if I should do it right here, and he goes “yea you can keep your boxers on though.”

Now here’s where I might have messed up. I’ve always just used boxers as a catch all term for men’s underwear, no matter what I was wearing. I think after googling a more accurate term for what I actually had on was “short boxer brief” or “trunk.” Maybe not the most manly thing in the world but I never really put much thought into it.

Anyway after I took my pants off the tailor got mad and said “no one wants to see that put your pants back on.” I apologize, saying that I thought that’s what he meant and he (a bit less annoyed) said “it’s alright I guess next time just say you’re not wearing boxers and we’ll keep the pants on.” The young guys find this hysterical. I also saw that there was another customer in the store but I don’t know if he came in after.

We get a measurement done in my jeans and I leave embarrassed. At first I’m mad but after explaining to my brother he said I probably made the guy uncomfortable and i was in the wrong. I didn’t think I needed to be more specific with him, but maybe I’m wrong. But either way I don’t know if he should’ve been so rude. AITA?

13 thoughts on “AITA for not being more specific with my tailor?”
  1. NTA that old man sounds homophobic to an extent that is actually interfering with his ability to do his job. It’s normal for a tailor to measure people while in their underwear, and I highly doubt every man who has ever seen a tailor wore baggy old fashioned boxers. If I were you I wouldn’t have thought anything about what type of underwear I was wearing. How is he supposed to get decent measurements over your jeans? 

  2. NTA, wtf. That’s a very weird assumption for him to make, and he was extremely unprofessional.

    I wouldn’t trust a tailor who is afraid of butts and nuts.

    1. Literally, how is he supposed to measure inner thighs?? Wear a special protection glove in case of nut to hand interaction?

      🌰👋

  3. NTA.

    But you’ll need to build resilience yourself soon – he doesn’t get to demand to know your underwear type, he doesn’t get to demand you get undressed in front of everyone, he doesn’t get to berate you about it, and you don’t need to worry about why two younger guys were laughing – young people are like hyenas.

    Pretty weird job choice – a tailor who doesn’t want to see men in states of undress/a tailor who doesn’t want to acknowledge the male body…

  4. NTA

    I wouldn’t go back to this tailor. You cannot trust him. And his comment to you was very rude and unprofessional.

  5. NTA, what an i d i o t. They should get a curtain in that store also! Send a complaint. This was just disrespectful

  6. NTA. Miscommunication about undressing is always the worst. I had a Dr appt where they said I should undress from the waist down but keep my top on. They failed to mention that there was a sheet to put over my lap for modesty. Very embarrassing to have the nurse come in and do a shocked laugh when I was Donald ducking it on the exam table.

  7. NTA.. of all of the men’s underwear I’ve seen, boxer-briefs/trunks are the more modest ones and would be relatively ideal for being measured. It’s a crapshoot whether or not regular boxers have a closure in the front and he’s probably more likely to tickle your nuts when measuring your inseam.. next time, wear a codpiece 🤣

  8. NTA

    I think that a lot of people would have taken the boxer comment as a “keep your undies on” statement and not as a specific call out for boxers only.

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