I figured it out. You just have to use some special selectors.

The problem with rounding the corners of the table was that the td elements didn't also become rounded. You can solve that by doing something like this:

table tr:last-child td:first-child {
    border-bottom-left-radius: 10px;
}

table tr:last-child td:last-child {
    border-bottom-right-radius: 10px;
}

Now everything rounds properly, except that there's still the issue of border-collapse: collapse breaking everything.

A workaround is to add border-spacing: 0 and leave the default border-collapse: separate on the table.

Compare method

Either you implement a compare-method for your object:

- (NSComparisonResult)compare:(Person *)otherObject {
    return [self.birthDate compare:otherObject.birthDate];
}

NSArray *sortedArray = [drinkDetails sortedArrayUsingSelector:@selector(compare:)];

NSSortDescriptor (better)

or usually even better:

NSSortDescriptor *sortDescriptor;
sortDescriptor = [[NSSortDescriptor alloc] initWithKey:@"birthDate"
                                           ascending:YES];
NSArray *sortedArray = [drinkDetails sortedArrayUsingDescriptors:@[sortDescriptor]];

You can easily sort by multiple keys by adding more than one to the array. Using custom comparator-methods is possible as well. Have a look at the documentation.

Blocks (shiny!)

There's also the possibility of sorting with a block since Mac OS X 10.6 and iOS 4:

NSArray *sortedArray;
sortedArray = [drinkDetails sortedArrayUsingComparator:^NSComparisonResult(Person *a, Person *b) {
    return [a.birthDate compare:b.birthDate];
}];

Performance

The -compare: and block-based methods will be quite a bit faster, in general, than using NSSortDescriptor as the latter relies on KVC. The primary advantage of the NSSortDescriptor method is that it provides a way to define your sort order using data, rather than code, which makes it easy to e.g. set things up so users can sort an NSTableView by clicking on the header row.