"Entry Level" Classic Dress Shirt and Gray Trousers

[AreTee]

I'm pretty young (23) and only recently started to appreciate the value of dressing well instead of dressing like a college student (been wearing jeans and wrinkled oxfords to work for the past year and a half since graduation...for shame...).

I have a decent job as a software developer (no real dress code) so I have some money to spend on clothes but since I don't really have much in the way of decent clothes I'm looking to get good value for my money. From lurking on here for a while I've picked up a ton of information and decided that there are two items I desperately need right now that are missing from my wardrobe: gray flannel trousers and a decently fitting dress shirt.

My best fitting dress shirt right now is a light blue BB ESF OCBD, but honestly it's still a bit off (plan to have it tailored soon). I'm 6'3'' 170lbs with ~31 in. waist so sizing shirts is a real pain.

So after all that introductory nonsense my question is: what would you all recommend for my first pair of gray flannel trousers and a decent dress shirt? There are so many choices, I'm really at a loss. Part of me says go for high quality since these are pieces that will never go out of style -- the other part of me says go for decent quality but on the cheaper end of the scale so I have more money left over for other outfits. What to do? I'm currently considering the following options:

On the higher end:
Sid Mashburn bespoke dress shirt, and probably pick up some flannel trousers while I'm there. I live in ATL so this won't be much of a drive and I understand it's high quality but also pretty high $$.

On the medium-end:
BB Milano Flannels, maybe get a BB shirt and have it altered in store to make sure it fits well with the trousers. I've also heard good things about Howard Yount but I would have to order that off the internet which I'm not super comfortable doing for my first pair.

Just realized that's a super long post but any help you guys could give me would be greatly appreciated!

 

[Liquidus]

What's scary about ordering off the internet? If you don't like it, just ship it back.

 

[AreTee]

It's not that it's scary it's just that for my first pair I feel like it would be better to feel the fabric in person and especially be able to try them on and get the fit just right (will have them tailored of course but would like to get at least "close"). Once I know the measurements for the fit I like then I will definitely be ordering online since I can find much better deals.

 

[atoms]

Depending on where you live, tailoring can actually get pretty damn expensive. Please call your tailor of choice and get quotes for adjusting sleeve length (by detaching the sleeve, not the placket) as well as tapering, adding darts, etc. It's going to vary a lot, but the best tailor I've found that's close by charges $35 for torso adjustments and $25 for sleeve. Other places may do the same work $25 total but you need to check.

Once you know how much alterations will actually cost you, you'll be able to make a better decision. Those online MTM shirts may be the smarter choice, even with a few send backs to get the fit right. Or, just ask your tailor straight up about their MTM shirt options. $110 for those is better than $60 + $65 for tailoring.

 

[duggyald]

There are so many options for online made to measure suits or shirts, but if you're ordering online you have to be sure of your measurements as some online MTMs will ask you for it before proceeding with your order.

 

[AreTee]

Well my worry with online MTM is that I don't really have any shirts I consider a really good for to have them copy. I could get my body measurements taken and go from there but I've seen that go sideways more than a few times on here and I'd rather not have to deal with the whole send it back, get adjustments, send it back again, etc.

One of the main reasons I'm considering paying for a truly bespoke shirt is I can actually talk to the tailor in person and we can be adjusting the fit while I'm actually wearing it. Once I get that one shirt that really fits well, I can just take the measurements from it and use them for online MTM shirts. I realize this will be more expensive for the first shirt but at least with bespoke I know I won't be wasting money on something that doesn't fit.