Went for an early 1950s 'hepcat' look today. Not wearing a tie for once was a little strange but I kinda liked it, just so I don't like it too much.
-early '50s 'atomic fleck' jacket
-'40s flannel trousers
-modern Florsheim shoes
click to enlargeAs you can see, the jacket is not form fitting like some jackets from the '30s and '40s. Remember, this was the time of the "Bold Look" when things were a little baggy and loose. However, even while things were loose, guys still wore their trousers up around their waists and in general did not look like slobs.
This is how dress casual should look today. Rather than pairing low-riding jeans with a jacket and tie (for that ironic look) why not wear classic garments (jacket, shirt, dress trousers) that are tastefully loose and comfortable but still sit up where they are supposed to, giving the wearer that stylish 'devil may care' attitude?