I’ve chosen a relaxed fit neutral colored striped shirt for the first option. The striped pattern helps camouflage the belly, and the fit is relaxed with broader shoulders and bodice. It will give you more room for your body shape. Also the V-neck of the shirt is the most flattering for a rectangular shape. You can get it in your regular Large size as it is a true to size fit.
These are dressy loafers in a sophisticated cut. They balance the natural fabric of the shirt and pants by bringing a polished effect. It follows the neutral color theme and the off-white rim matches the shirt. It runs half a size large, so purchase accordingly.
Accessories in a similar shade of brown as the shoes for a put together look. The watch as well as the wallet are very minimal and understated, perfectly suiting your personal style.