The shape of single-side wind fairing, which is the longitudinal triangular prism that tailors the outer side of a bridge deck, is key to the aerodynamic performances of double streamlined box girders used in long-span bridges. Uniform flow past single and double 4:1 rectangular cylinders with various single-side fairings are investigated using large-eddy simulation at a Reynolds number of 1.1 × 104. Various fairing nose angles and heights are compared. The wind loading and flow characteristics of the cylinders are discussed. The upstream fairing shows a larger reduction of mean drag and fluctuating lift on double cylinders than on a single cylinder. The fairing nose angle has a stronger influence on the wind loading than the nose height. By adding the fairing, sharpening the fairing nose, or lifting the fairing nose, the lateral recirculation zones are shortened while the rear recirculation zone barely changes, leading to different influences on the surface pressure. The upstream fairing is effective in reducing the vertical range and complexity of vortex structures around single and double cylinders.