Recently we got to talking about the five things that every man of style aspires to own at some point in his life. While most will never get near assembling the full collection, in some way many of us will come close to obtaining items that are at least in the same sphere; a Rolex Submariner is better than no Rolex at all, and even a modern Porsche 911 has panache. By definition, though these things are more precious than a pair of Persols or a Ghurka bag; our starting five are more like lifelong achievements and as such come with considerable price tags. This isn’t a mandate, but if you had the means, this is the direction we think you should beheaded.

You don’t have to have lots of money to have style, naturally, but it certainly comes in handy when acquiring all the right stuff. Of course, the really resourceful man can always come up with stylish alternatives that cost less. Guys who are not only really into the classics but also have the means to collect these truly iconic items however all have their own take on The List, and some may have other ideas altogether; which is why we’re also inaugurating 5 Icons as a new ACL feature, starting with our man Matt Jacobson below. Check out the five holy grails we’ve gathered together and let us know what you think we’re missing:

1. Vintage Porsche 911

The exact year doesn’t really matter, as long as it’s from the first generation, 1965–1989, and the older the better. We like all our stuff with its original patina but a lot of hardcore collectors prefer cars in near-concours condition.

2. Paul Newman Rolex Daytona

There are only six references that make the grade from the ’60s and ’70s, and all of them are now expensive as hell. Buyer beware as even early Daytonas from the same year as Newmans don’t qualify without the quirky dials. Hodinkee breaks it down here.

3. Leica Camera

Potentially the easiest acquisition price-wise, though as with anything else once you start getting into the fine points costs rise. A bit of research should net you an older film version comparatively cheaply, while high megapixel digital models fetch a premium.

4. Land Rover Defender

N.A.S. (North American Spec) Defenders were only sold in the U.S. from 1993–1997. You could buy an earlier model or import a more modern one at insane cost, but as with the 911 older is always cooler in any case.

5. Bespoke Savile Row Suit

Except to the highly trained eye, this is one item that doesn’t really proclaim its label to everyone you meet, which of course makes it all the more rewarding to own. Having a suit custom made is a rite of passage for any man of style, making it to Savile Row is sheer nirvana.

(photo: Hodinkee)

Matt Jacobson is a watch and car collector, as well as the gent behind Grown Man Style and several entrepreneurial enterprises. Here’s his take:

1. “1973 Porsche 911S. Last year of the small bumpers. Alternatively, the 1955 VW Beetle. Last year of semaphore turn signals on an Oval VW. Also, my VW passion has been vindicated by the prices at Amelia Island this weekend.”

2. “Maybe an early early [Daytona] or Sea–Dweller is more iconic. When you see a guy wearing one with a suit, you really know something about him – surfer, sailor – whereas you don’t with the Paul Newman.”

3. “Leica Monochrom. The true essence of Leica photography is black and white. Think Jim Marshall and Henri Cartier-Bresson.”

4. “1997 Defender 90 SW (hard top wagon), the only North American year with A/C and automatic transmission. Also, the last year imported to the U.S.”

5. “An Anderson & Sheppard suit or a pair of Alden for Brooks Brothers shell cordovan penny loafers. Those shoes are completely iconic, one of a kind, only available unlined (more comfortable) from Brooks.”