2 grand is such a great budget, you could probably have one made to your specifications by a reputable manufacturer. I have a Shinola leather briefcase that will almost certainly last forever since I only use if for offsite meetings (around 20 days a year), it’s cheaper than the Clegg, looks good and is unlikely to go out of style.

For day to day I use a Tumi, I’ve had it for 5 years and it’s still in good shape. Not formal or leather, and unlikely to catch any eyes among the Brioni crowd, but it’s a very durable and useful case.