Granted... this may be strange, but bear with me.
Iron Man models and their development have always in some ways reminded me of the evolution of US military jet fighters.
What the heck am I talking about?
The original grey model has got to be the F-86 Sabre of Iron Man armors.
Iron Man original grey introduced in March 1963.
http://marvel.wikia.com/Iron_Man_Armor_MK_I
First-generation jet fighter the North American F86 Sabre introduced in 1949.
http://en.wikipedia.org/wiki/North_American_F-86_Sabre
Note: Dates for the introduction of the armors are the cover dates rather than the actual publication date of the issue.
Next up the original red and gold armor, the Iron Manual designates the Model II and the F-104 Starfighter. Sleeker and faster than its predecessors both represent a step forward in tech and design.
Original red and gold Armor first appeared in December 1963.
http://marvel.wikia.com/Iron_Man_Armor_MK_III
Lockheed F104 Starfighter introduced in February 1958.
http://en.wikipedia.org/wiki/Lockheed_F-104_Starfighter
The classic Iron Man armor and what I consider the classic American jet fighter, the F4 Phantom.
Iron Man Classic first appeared Iron Man vol I, issue 86 in April 1976.
http://marvel.wikia.com/Iron_Man_Armor_MK_V
3rd generation jet fighter McDonnell Douglas F-4 Phantom II introduced December 1960.
http://en.wikipedia.org/wiki/McDonne...F-4_Phantom_II
Not a jet fighter, but the time periods match up too closely for me not to post!
Next up we have the first specialty armor, the original Space armor and the NASA’s Space Shuttle.
Mark I Space Armor introduced Iron Man vol I, 142 in January 1981.
http://marvel.wikia.com/Space_Armor_MK_I
NASA Space Shuttle had its first flight in April 1981 (so Iron Man got there first).
http://en.wikipedia.org/wiki/Space_Shuttle
The second specialty armor, this one sacrificed firepower for electronic invisibility and detection systems. This fighter flew for years before anyone even admitted to its existence, the F117 Nighthawk.
The first Stealth armor appeared over the night skies of Germany in Iron Man vol I, 152 in November 1981.
http://marvel.wikia.com/Iron_Man_Armor_Model_07
Lockheed F117 Nighthawk introduced in October 1983.
http://en.wikipedia.org/wiki/Lockheed_F-117_Nighthawk
The Silver Centurion and the true star of Top Gun, the F14 Tomcat. Both big and armed to the teeth.
Silver Centurion appeared in Iron Man vol I, 200 as of Nov 1985
http://marvel.wikia.com/Iron_Man_Armor_MK_VII
Grumman F14 Tomcat introduced September 1974.
http://en.wikipedia.org/wiki/Grumman_F-14_Tomcat
At around this period in time, I will admit the choice for the next fighter in the progression becomes somewhat less clear, but I will go based largely on date of introduction rather than capability.
The "new" red and gold borrowed from technology gleamed from his enemies, while the F15 Eagle was one of the most successful designs of its period.
The new red and gold armor was introduced in June 1988
http://marvel.wikia.com/Iron_Man_Armor_MK_VIII
The McDonnell Douglas F-15 Eagle entered service in June 1976.
http://en.wikipedia.org/wiki/McDonne...las_F-15_Eagle
The Variable Threat Response Suit or War Machine armor and the only aircraft I can think of as a suitable analogy to it, the A10 Thunderbolt! Not sleek nor subtle, but more than capable of ruining someone's day, their week or even their year.
War Machine armor first appeared Iron Man vol I, 281 June 1992
http://marvel.wikia.com/War_Machine_...28JRXL-1000%29
Fairchild Republic A-10 Thunderbolt II introduced March 1977.
http://en.wikipedia.org/wiki/Fairchi...Thunderbolt_II
The Neuromimetic Teleprescence Unit 150 and the Predator drone. Lay waste to your enemies from the comfort and safety of your living room. Not very heroic, but you can't argue its not effective. While the Predator isn't a jet fighter per se, the NTU 150 isn't exactly an armor either.
Teleprescence armor introduced March 1993.
http://marvel.wikia.com/Telepresence_Armor
General Atomics MQ-1 Predator introduced June 1995.
http://en.wikipedia.org/wiki/General..._MQ-1_Predator
A departure in terms of design philosophy the Modular armor was the first configurable armor, but in some ways less outright powerful than earlier models. Similarly our next aircraft, the F16 Fighting Falcon was smaller, slower, and carried less armament despite being more economical and agile than the older aircraft.
Modular Armor introduced Jan 1994.
http://marvel.wikia.com/Modular_Armor
General Dynamics F-16 Fighting Falcon, August 1978.
http://en.wikipedia.org/wiki/General...ighting_Falcon