Q and Answer: Black Tie
Josh writes:
I want ONE tux that will be stylish AND timeless.  Does this exist? 
I know I’ll be in a wedding next May where I’ll be invited to wear my own tux but will be given a matching long tie to match with other groomsmen.  Should I go with a two or three button jacket to pull off the tie?  Or does the classic one button notch lapel work (depending on shirt) with any combination?    I am leaning towards the classic one button, so that I can work btoh looks.  I was recetnly told that bowties are, in general, “out” at the moment, and I’d be more stylish at an upcoming chartiy event in a vest/tie combo…1) is this true, and 12) can I pull it off in the classic one button? Any SPECIFIC advice on what to buy?  I don’t really have a price limit (which is admittedly helpful), and am willing to travel to make the right tux happen for me. 
If anything in men’s clothing is a true classic, it is black tie.  So the short answer is an unequivocal “yes.”
The Platonic ideal for black tie is midnight blue, single-breasted, with a single button, a peak lapel, and grosgrain facings on the lapel.  The facing should match the (self-tie) bow tie and cummerbund. The pants are pleated and without a cuff.  The shirt features a detachable wing collar, French cuffs and a pique bib.  Opera pumps are worn with black silk hose.  The pants are held up with suspenders that fasten with buttons, and the shirt is closed with studs.
There is room for other options, of course.
In the absence of midnight blue cloth, black can be used.  (Midnight blue is more attractive in low and artificial light.)
Facings can be satin instead of grosgrain. 
In warm weather, an ivory dinner jacket is an appropriate substitute for the traditional jacket.
A pleated shirt with a turndown collar can be substituted for the wing collar.  (Slightly less formal.)
A shawl lapel can be used rather than peak.  (Again, less formal.)
The jacket can be double-breasted, particularly if you are tall and thin.  (Again, less formal - and remember to leave your cummerbund at home.)
You can substitute a waistcoat in the same material as the coat for the cummerbund.
Patent oxfords can be worn in favor of opera pumps.
The pants need not be pleated.
A white pocket square (preferably linen) or a boutonniere can be added.
If you’re in a homier black-tie environment - a friendly party, entertaining, that sort of thing - you can wear a velvet dinner jacket or slippers.
That’s the basics of black tie.  Oh - and remember that black tie is for evening social occasions.  The stroller is the equivalent to black tie for daytime wear, and morning dress the more formal alternative.  About 6PM should be the cut-off.
As per your specific concerns:
A long tie should not be worn with a tuxedo.  Can you imagine if we let the groom pick the bridesmaids’ outfits?  Oof.  Of course, it’s not worth starting a fight over, so just get something good and do what they say this time.  I’d say getting a tux with a waistcoat and a shirt with turn-down lapels would help cover for the long tie’s blech factor.
Bow ties are most certainly not out, especially for black tie.  In fact, I can’t think of a time within the last 25 years that bow ties have been more in.  And like I said - long tie in your black tie ensemble?  Blech.
Never, ever buy a notch-lapel tuxedo.  Again: blech.
A vest is perfectly fine with a one-button tuxedo.  But not with a long tie.
And as for where to buy?
Well, with a tuxedo, you have some great options.
The classic tuxedo has changed little in the last 75 years, and they’re used too infrequently to wear out, so vintage is a good way to save money.  My own tuxedo was made in the late 30s, and cost me less than $30.  If I bought a tuxedo of comparable quality new, it would cost me a few thousand.  If you’re buying vintage, remember that fit is key.  Many vintage pants and sleeves have some wear at their ends, and can’t be lengthened (or there will be a stripe of wear).  Shoulder width is very difficult to alter, as is jacket length, and the chest should fit within an inch or (at most) two.
If you want to buy something new for cheap, your options are few-ish.  Jos. A Bank sells tuxedos of not-horrible quality, and if you catch one of their astonishingly frequent 50-75% off sales, you can get one at a reasonable price.  It’ll be better than a rental (which tend to be of abysmal quality), though not the heirloom a better tux would be.
If you want to buy at retail, your best bets will likely come from Ralph Lauren.  Ralph’s English-y WASP obsession makes for classic evening wear.  Polo dinner suits are very good quality, and Purple Label are even better.  Brooks Brothers can also be a good choice, though their better-quality Golden Fleece line is cut for an older, stockier man.
If money isn’t an issue, though, why not go made-to-measure, or even bespoke?  Find some beautiful fabric, and have a tailor like Joe Hemrajani of MyTailor.com suit you up.  You’ll have full control over the process and a perfect fit.  And if you really want to spend some money?  Get your self a ticket to London and visit Savile Row.  Most of the tailors will gladly help arrange fittings for you - though you may have to visit more than once.  Some, like Norton & Sons, offer US fittings as well.
And if you need guidance more thorough than this, check out Black Tie Guide, one of the internet’s best men’s clothing resources.

Q and Answer: Black Tie

Josh writes:

I want ONE tux that will be stylish AND timeless.  Does this exist?

I know I’ll be in a wedding next May where I’ll be invited to wear my own tux but will be given a matching long tie to match with other groomsmen.  Should I go with a two or three button jacket to pull off the tie?  Or does the classic one button notch lapel work (depending on shirt) with any combination? I am leaning towards the classic one button, so that I can work btoh looks.  I was recetnly told that bowties are, in general, “out” at the moment, and I’d be more stylish at an upcoming chartiy event in a vest/tie combo…1) is this true, and 12) can I pull it off in the classic one button?
Any SPECIFIC advice on what to buy?  I don’t really have a price limit (which is admittedly helpful), and am willing to travel to make the right tux happen for me.

If anything in men’s clothing is a true classic, it is black tie.  So the short answer is an unequivocal “yes.”

The Platonic ideal for black tie is midnight blue, single-breasted, with a single button, a peak lapel, and grosgrain facings on the lapel.  The facing should match the (self-tie) bow tie and cummerbund. The pants are pleated and without a cuff.  The shirt features a detachable wing collar, French cuffs and a pique bib.  Opera pumps are worn with black silk hose.  The pants are held up with suspenders that fasten with buttons, and the shirt is closed with studs.

There is room for other options, of course.

  • In the absence of midnight blue cloth, black can be used.  (Midnight blue is more attractive in low and artificial light.)
  • Facings can be satin instead of grosgrain.
  • In warm weather, an ivory dinner jacket is an appropriate substitute for the traditional jacket.
  • A pleated shirt with a turndown collar can be substituted for the wing collar.  (Slightly less formal.)
  • A shawl lapel can be used rather than peak.  (Again, less formal.)
  • The jacket can be double-breasted, particularly if you are tall and thin.  (Again, less formal - and remember to leave your cummerbund at home.)
  • You can substitute a waistcoat in the same material as the coat for the cummerbund.
  • Patent oxfords can be worn in favor of opera pumps.
  • The pants need not be pleated.
  • A white pocket square (preferably linen) or a boutonniere can be added.
  • If you’re in a homier black-tie environment - a friendly party, entertaining, that sort of thing - you can wear a velvet dinner jacket or slippers.

That’s the basics of black tie.  Oh - and remember that black tie is for evening social occasions.  The stroller is the equivalent to black tie for daytime wear, and morning dress the more formal alternative.  About 6PM should be the cut-off.

As per your specific concerns:

A long tie should not be worn with a tuxedo.  Can you imagine if we let the groom pick the bridesmaids’ outfits?  Oof.  Of course, it’s not worth starting a fight over, so just get something good and do what they say this time.  I’d say getting a tux with a waistcoat and a shirt with turn-down lapels would help cover for the long tie’s blech factor.

Bow ties are most certainly not out, especially for black tie.  In fact, I can’t think of a time within the last 25 years that bow ties have been more in.  And like I said - long tie in your black tie ensemble?  Blech.

Never, ever buy a notch-lapel tuxedo.  Again: blech.

A vest is perfectly fine with a one-button tuxedo.  But not with a long tie.

And as for where to buy?

Well, with a tuxedo, you have some great options.

The classic tuxedo has changed little in the last 75 years, and they’re used too infrequently to wear out, so vintage is a good way to save money.  My own tuxedo was made in the late 30s, and cost me less than $30.  If I bought a tuxedo of comparable quality new, it would cost me a few thousand.  If you’re buying vintage, remember that fit is key.  Many vintage pants and sleeves have some wear at their ends, and can’t be lengthened (or there will be a stripe of wear).  Shoulder width is very difficult to alter, as is jacket length, and the chest should fit within an inch or (at most) two.

If you want to buy something new for cheap, your options are few-ish.  Jos. A Bank sells tuxedos of not-horrible quality, and if you catch one of their astonishingly frequent 50-75% off sales, you can get one at a reasonable price.  It’ll be better than a rental (which tend to be of abysmal quality), though not the heirloom a better tux would be.

If you want to buy at retail, your best bets will likely come from Ralph Lauren.  Ralph’s English-y WASP obsession makes for classic evening wear.  Polo dinner suits are very good quality, and Purple Label are even better.  Brooks Brothers can also be a good choice, though their better-quality Golden Fleece line is cut for an older, stockier man.

If money isn’t an issue, though, why not go made-to-measure, or even bespoke?  Find some beautiful fabric, and have a tailor like Joe Hemrajani of MyTailor.com suit you up.  You’ll have full control over the process and a perfect fit.  And if you really want to spend some money?  Get your self a ticket to London and visit Savile Row.  Most of the tailors will gladly help arrange fittings for you - though you may have to visit more than once.  Some, like Norton & Sons, offer US fittings as well.

And if you need guidance more thorough than this, check out Black Tie Guide, one of the internet’s best men’s clothing resources.