Looks like they're both running 1x so I'd say post-2015.
V-CC: I suspect that these photos do not date from when the toeclips or the bikes were brand-new . Personally, I would date the photo as having been taken between 1905-1910, some years after the toeclips were first introduced. (How many of our own photos with our bikes were taken on the day that we purchased them new?) It takes time for new technological developments (pneumatic tires, toeclips, brakes, etc.) or new fashion styles to penetrate the market and be adopted...
It dates to late 1890s. The cycle in the background is older than the other - perhaps 1897. The foreground cycle perhaps 1899. Both have inch pitch chain. The cycle in the foreground has toe clips that are illustrated in this Ravenscroft catalogue of 1899. Note no straps.
View attachment 706753
Could do more work on identification if there is interest.