My day job is in investment management, so I spend a lot of time participating in discussions about what makes a good investment.  If I’ve learned anything over the last year or so, it’s that retail may be a very BAD investment.  And fashion may fall on the far end of that spectrum.  BCBG, J.Crew, Neiman Marcus, Nine West … all of these companies have either filed for bankruptcy or are seriously struggling.  But that doesn’t stop me from doing my part to keep retailers afloat!  Rather than a portfolio of securities, I have a portfolio of clothes, shoes and handbags, and if Neiman Marcus files for bankruptcy, it’s going to do so in spite of my contributions to its bottom line.

Whenever I buy something really nice, I tell myself it’s an “investment piece,” even though I know this concept is basically just my psychological excuse to splurge.  I’m fairly certain that my fashion portfolio will, in large part, not be a wealth creator for me, but I do think there are such things as investment pieces, which in my mind take one of two forms.  The first are those pieces that you’ll wear so much and feel so great in that you’ll definitely get your money’s worth.  The second are a lot fewer and far between … those pieces that you will actually be able to resell as “vintage” down the road, perhaps even at a gain.

I think everyone should definitely have some investment pieces in the first category.  For women, I think they include a great pair of black pumps (maybe Christian Louboutin because everyone knows the red soles), a cashmere V-neck sweater (which can be paired with everything from slacks to skirts to jeans), a fabulous little black dress and a good handbag (a lot of women choose Louis Vuitton, but I prefer something a little more creative like Pierre Hardy).  For men, I think they include a made-to-measure suit (because every girl’s crazy ’bout a sharp-dressed man AND she notices the stitching on the outside), a good pair of dress shoes and a cashmere pullover (good for lending out to the ladies when they get cold).

As for the second category, that’s A LOT harder.  I think you kind of have to trust your eye about what will survive the test of time.  Chanel has generally been a good bet … I think in large part because the company has so tightly controlled supply and distribution.  But occasionally you’ll see something from a designer that is so amazing and special that you’re willing to bet a few paychecks that it will end up in the Met Costume Institute one day.

I felt that way when I saw this Alexander McQueen leather peplum jacket with embroidery that I got from Net-a-Porter (http://www.net-a-porter.com).  It’s so unique and well crafted … a real work of art.  And I paired it with a Neil Barrett leather skirt I got from Farfetch (http://www.farfetch.com).  For me, this is better than any Facebook or Twitter stock I could own …