Hi Tralynn! The Work and the Twiggy are 2 very different styles. I have both and love them for the different purposes they serve. Let see now,
The Work - it is a good large sized bag which holds way more than the City. But it could be a bit hard to locate things in there because it is quite deep and wide. And I find people tend to bump into the back edges of it when I carry it in crowded spaces.
It is a great size for travelling though - you can easily fit in several small purchases from duty-free along with a light jacket, passport, wallet and the usual travel essentials.
The Twiggy - it is about the same size as a City but is more east-west in its look because it is not as 'tall' as a City. It does whatever a City does and I use these 2 interchangeably. I really like the look of the Twiggy. It is cute without being too small to function as a proper bag for someone who carries more than a wallet and make-up pouch. It fits a cardigan and even a small brolly! I can imagine using it as a travelling bag but only if I don't want to carry too much on the flight.
Hope this helps!