I have been golfing for more than 50 years and would like to begin a discussion between about old clubs vs new clubs. I am dividing the categories into drivers, fairway woods, hybrids, irons, wedges, and putters. I have been caddying for the past 25 years, mostly part-time, and have seen most makes and models of name brand clubs.
Drivers: Personally, I feel that drivers have seen the most development in the last 20 years. Head size, shaft technology, and adjustability have made major advancements. Two decades ago I played actual persimmon drivers, as well as a metal driver call the TaylorMade Pittsburgh Persimmon Driver. Now I play a non-adjustable Ping G5 (9°), and an adjustable TaylorMade R11 (10.5° adjusted to 9.5°.
Fairway woods: Until the 1980's fairway woods were actually made of wood, and after that metal woods took over Ever since TaylorMade got into the metal woods business, I have always felt that they are, by far, the best fairway woods in the business. In 1991 I purchased a TM System 2 17° Raylor, and it is still in my bag. Obviously, I feel that there have not been enough significant improvements for me to change. I am still looking for a new 3 wood and will probably break down and get a TMRocketballz in the near future. This club has recently found its way into a lot of golf bags, and I have seen first hand evidence that it is a step above older technology.
Hybrids: TaylorMade designed their original Rescue club in the 1990's to bridge the gap between irons and woods. Golf manufacturers took this club a step farther and the hybrid was born. I love these clubs because I no longer have to worry about my short comings with 2 or 3 irons as I pull our my TaylorMade Rescue Mid TP (19°). Generally it is long and straight and has the ability to hit "knock down" shots under branches or high arcing shots over trees and bushes.
Irons: As a youth I hit Hogan Apex blades, and when I found the sweet spot I could actually move the ball left to right or right to left as I pleased. However, as I got older, hitting the sweet spot got harder and harder. In 1990, I got my first set of perimeter weighted clubs, the original Hogan Edge irons. I still use them in the winter, and in the summer I play Ping i3+. Both sets of irons are 4-pitching wedge and have a solid feel, even on off-center hits. But the Pings, (to me), are a little more consistent. I have seen the newest irons and find that they are longer than older clubs. But, in large part this has been due to strengthening the loft of the clubs. (EX: older pitching wedges were 48°, and current pitching wedges are 45°-47°.
Wedges: Cleveland was the choice of pros. From Cleveland Golf, "For over 30 years, Cleveland Golf has been a leader in wedges. From the Cleveland Classic wedge of the early 1980s to the 588 Forged of today, Cleveland Golf has set the standard in wedge design..." I played Cleveland, as did my friends. Recently, Titleist Vokey wedges have challenged Cleveland for wedge supremacy. I, however, put a Ping Eye2 BeCu lob wedge (60°) in my bag in 1990, and it has never left. To bridge the gap between the 48° PW in my iron set and the 60° Ping lob wedge, I have a 54° Ping ISI BeCu sand wedge.
Putters: Having grown up with the Spaulding "Cash-In," Titleist "Bullseye," and Wilson "8802" putters, I really appreciated the Karsten Solheim evolution of the perimeter weighted putter so that by the 1970's the majority of putters used in the PGA and tournaments were Ping. Since then the overall design (2-Ball, SeeMore, etc.) and the length of the putters have played a significant role in putter development. In the '80's I went to the Anser and B60 putters. I periodically try an Odyssey (XG #9 and 2-Ball) putter and find that, in the end, it is not the putter, by the puttee.
In closing, I don't see a need to change most of my older clubs in favor of newer models with the exception of the driver. I guess as I grow older I need something to help me find those few extra yards off of the tee.