New York
When thinking about clothing purchases, the second context I use is, "Would it work for an evening event in a major city?"
This is the only context in which I consider the color black, and one of the few where I consider dry-clean only items. Ideally, an outfit transitions smoothly (with a few additions) from a day of meetings to an evening out.
Even here, practically has to be a consideration. Weather can change quickly. If taxis are scarce or comradery high, one may walk for several blocks or more, so clever footwear may be needed.
Here are some of my images:

New York

New York

Taipei

Cosmos Club, Washington, DC

Toronto


6 comments:
Don't know about women, but the trend to "less formal" wear makes it relatively easy for men.
Blazer always works.
OCBD with a tie gets you by in a lot of places, simply because the tie adds a look of being "well dressed". Most men don't wear a tie at all, so this seems to be a plus.
Grey trousers. makes the whole get up work, almost as well as a suit.
With men's shoes, weather and a touch of formality can be covered with any number of Alder lace ups, that are in fact water repellant. This doesn't seem like a big deal until you are standing in snow, salt, or water, trying to get a cab.
Top coat, and fedora will finish things off so that you look about as well dressed as you need to be, and better than most, IMO. From Four Seasons, to the Met, to Dizzy's Coca Cola, or so it has seemed to me.
Wharf Rat, I must tell you honestly; it's not true that 'blazer always works." There are many situations in the cities Muffy cites in which a suit, or a d.j., or even white tie might be in order for gentlemen. You surely can wear the blazer for drinks at the British Embassy, but not to the opera or to various political or cultural events.
Would have agreed with you 20 years ago, Andrea. However, the way most men dress has deteriorated to the degree that a blazer has replaced the suit in most situations calling for being "properly dressed".
Blazer plus a tie puts you in a category of being better dressed in situations now, where "jacket and tie required" is now looked upon as quaint.
Travel on commercial airlines at one time called for a suit. Now...... ugh!
At the MET, few men now wear ties. Most look like they don't own one. Evenings that called for a dinner jacket there, are a thing of the past.
I agree with Muffy, when she said that no one in her family owns anything denim. However, that view, is also now sadly in the minority.
Not that any of this is good, but just the way things are.
We may travel in different circles, Rat. Blazers and seersucker are fine at the University Club or the Virginia Foxhound Show, but for giving speeches, engaging in negotiations, or dealing with law firms you will need a good suit, while for charity balls you will need a dinner jacket.
I was just in NYC last weekend and had to walk around the plaza. I have been thiking of doing an overnight at the Cosmos Club soon...we are in Baltimore so it's very close! xx
I'm with Wharf Rat. Socially, a blazer and tie seems to cut it mot places, and I wear a suit to the office!
My family has been members of the Cosmos Club dating back four generations. I know it well.
Reggie
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