Good thread. It's amazing how little you really need, once you figure exactly what your taste is, sticking with the best quality you can afford, and avoiding anything that looks like a bargain, if it doesn't fit your taste, exactly.

Everyone here has different taste, so the answers on a basic minimum will vary all over the place, with obviously, no correct answers.

Somewhere in every Ivy closet, it is usually easy to find:

Blue blazer, or two;
A bunch of OCBDs that look a lot alike (I agree with your rapture in discovering the MTM club collar, at BB.) In the OCBD vernacular, the collar roll is the first thing to look at. BB gotta irons, and Mercers are perfect;
A bunch of khakis. You may find that you will have poplin for summer, 8.5 oz Bills', and Flannel lined;
Grey trousers, maybe charcoal, and oxford grey;
A bunch of BB sized merino wool sox in grey and black:
Rep ties, critter motif ties, and a solid wool or two;
Bass, LLB bluchers, Alden tassels, cordovan wingtip, and maybe an Alden black 901, cap toe;
Depending on your job, as many sack Ivy 3/2 roll suits as you need;
A seersucker jacket for summer, and a pair of white bucks, if you're so inclined;
Barbour, or Filson jacket;
Shetland wool sweaters, with saddle shoulder;
Heavy wool JP overcoat, Burberry like midweight, and JP or BB raincoat.
About 4 plain grey sweatshirts, sans logo;
Madras half sleeve, or polo for warm weather. Just go with OCBD with sleeves folded back, if it suits you.
Maybe a dinner jacket with shawl collar, if you have need for one. Wear you Alden, black 901s with it.

Others will have drastically different ideas. but once you figure our who you are, you are set for life. These styles will never change, and the only things you discard are things that wear out.

S'funny - I'm not aware of any mid-life crisis but rather the reverse - Some kind of mid-life re-grouping...
A return of my old intolerance for BS wherever I find it and a re-focusing on my first loves of Jazz & Ivy.
Also a desire to return to urban life - Back to my roots. What the hell am I doing in a cottage down a leafy lane? It must have been when my Father died & I became a farther myself that I made a few 'interesting' decisions. I'm glad I'm feeling much better now...

... And clothes do come into all this: The return to a clearer vision of my personal style. No fripperies. Something 'harder' like back when I started out...

Odd.

Interesting.

I believe in my soul on a good day.

Other days I coast.

Lately (maybe nostalgia for my youth) I have been going for a more "heavy ivy" or 70's and early 80's version. More realistic than the various online discussion boards would have you beleive. Red Wing workboots or weejuns with Levis 501 or cords. I have an old Bean norwegian sweater, and plan to invest in a Scandinavian-style sweater this winter.

Pre-OPH, but more real life, for sure. I will continue to wear occasional bright colors, but no 80's fads please.

Any other fans of this era?

I'm setting foot out of the house today in Black Watch footer bags.  My spirit is delightfully tainted.

Levis, weejuns, Redwing crepe soled workboots, Burlingtons, Clubmaster frames, suede or leather 3/4 jacket with leather football buttons, cord, Smedley roll necks, Hanes beefy T's, soft check shirts with loop collars, desert boots, Duffle coat, university scarf, worn Levis khakis, buckle back drivers cap, Playboy chukkas, plain grey sweatshirt... Boho Ivy?

... "I wear a suit or a sportscoat most days"... "Bow ties at least three times a week"...

^ And then he calls three piece suits "vested suits". Wot a Pleb.

Hello Shuman. Burlingtons are a quality sock brand here in Britain. More famous for their Argyle patterns.

Ah yes. I realized that once posted. Too quick on the keyboard.

Perhaps this should have been its own thread.

Actual Ivy vs. Media Ivy? 

(I, for one, enjoy the historical more than the caricature. How these items were really worn.)