When you view a folder where you've stored some pictures on your hard drive (or elsewhere), ensure that 'Details' is chosen as the selected view. (Depending upon your version of Windows you either need to click on 'View' or on 'More Options' (from the downward arrow next to the 'Change your view' icon) to select it.
You should then see 'Name', 'Date', etc as column headings. Right-click on one of them to add additional columns to the display, such as 'Date taken', 'Date modified', etc). Clicking on a column heading orders the list according to that heading. (e.g. clicking on 'Date taken' puts everything into date order. Clicking again reverse the list). You can then select the first file that you want to copy across to your USB stick by clicking on it. Hold down shift and click on the last one, so that the whole block is selected. Then drag-&-drop (or copy-&-paste) as normal.