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Depends on the pants and the tailor. Most RTW pants should have enough seam allowance to be let out an inch. But a lazy tailor may just let it all out from the center back seam, which can alter the fit of the seat and spread the pockets too far apart. The better way is to let out a little bit from each side, either instead of or in addition to from the center.

Would you wear a bow-tie with a cutaway collar or an extreme-cutaway collar? Thanks

NO.

+1.

I'm a 17-year-old boy, can I wear a trench coat to high school ?

No.

No.

Thanks for the quick answer, that's what I thought, though I'd really like to... I guess I'll just have to wait a few years then.

For a blazer what size mm buttons should I get for the 2 front buttons? And what size for the 4 cuff buttons on each side?

I'd honestly say it depends.

 

Are you in MCJROTC? 

Is it Humphrey Bogart Day?

 

Do you have grey hair?

 

... is it raining?

 

Seriously, though. Wear a suit or something if you want to stand out.

Do I need to put shoe trees in my unlined Chukka Boots or will the constant pressure stretch out the suede?

I'm going to buy my first pair of Allen Edmonds shoes soon. This will be my first pair of quality shoes and I'm having trouble deciding which color to get. My first instinct was black PA's because my suit is black, but I only wear my suit a max of 4 days a year. My daily wear consists of pants in varying shades of grey and solid color dress shirts. So should I buy brown shoes and continue to wear the cheap but passable black shoes with my suit, or buy black first and build out to browns from there?

Since your daily wear consists of casual clothes, I would get casual shoes, preferably something in brown, as you said. Just don't wear them every day. At most, you should wear them every other day, at least if you want them to last for a while. Put shoe trees in them when not wearing.

+1 to all of this.

Every so often, someone asks a question suggesting that he fears shoe trees will stretch out and harm his shoes (especially if they're suede).

The answer, as always, is that unless the tree is grossly mismatched to the size of the shoe (like, somehow forcing a size XL shoe tree into a size 7 shoe, not that this is something one is likely to manage), shoe trees will not damage shoes. Not calfskin shoes. Not horse ass leather shoes. Not suede shoes. Not shoes made from the skin of the rare fire-spitting zebra lizard of the south-central Garnath Valley, near Mount Kolvir. Shoe tree use will tend to be beneficial to shoes. It will not hurt shoes.