If you tell them to take in the sides, they'll only take in the sides. When speaking with a tailor you gotta be really, really specific. Don't just assume they know what you mean, unless you've had the tailor for a long time. Didn't the tailor pin the shirt on the spot for you? You should have known that it would have been too baggy from there, and then asked for darts in addition or just plain darts. How much was the shirt taken in? It sounds pretty extreme, as I've taken in shirts and they have been perfectly fine on the top block. Whenever I've done darts they've run from yoke to hem, so that's common practice. H&M does these types of darts. Though as the dart gets further up it doesn't "take in" the shirt as much as say, the waist, so often times you can ask for them to stop the darting before the yoke as well. Also, he wanted to keep the box pleat because it's a lot of extra work to remove the pleat, cause you kind of have to deconstruct part of the shirt and then put it back together. My mum has been tailoring clothes for about four decades now and runs her own place, and I used to help her in the shop a lot, so I hope this was kind of insightful? Thanks for the input! Yeah I definitely know you have to be specific and sometimes hard-nosed with tailors. I've had to change tailors a few times, and at least once because the guy was old school and would not do something slim enough. It wasn't a proportion issue, he just didn't believe in cutting something that slim. In this case, the original lady swore up and down it would look fine taking in the sides alone (she gave me some BS about it needing to be pressed and my excuse is that I was tired after work). I disagreed and should've pushed harder on it but even after asking twice, she insisted on sides only. Everything worked out fine as that shirt is being re-done free of charge. I knew removing the box pleat would be work, just wasn't sure how much. Re: darts to yoke, I've been working out and losing weight so my body shape has changed a bit (waist size dropping quickly, shoulders and back growing slowly). The dart up to the yoke was 100% necessary because, as I said before, I was getting a ridiculous turtle shell blousing effect. It's probably always been there but narrowing the waist area likely made a the problem look more ridiculous. Pint glass to wine glass, n'amsayin'?