Keep him warm with a Schiesser undershirt. A Swiss company started in 1875.
Top it off with a North Sea Engineer jumper. A new company created by a collector of vintage military and workwear their range is inspired by submariner uniforms of WW2.
Get him some 1000 mile Wolverine boots. They've been making boots for over 125 years. These are inspired by turn of the century work boots.
You will of course have knitted him socks using a WW2 Red Cross pattern.
A Japanese selvege senim work apron for when he's fixing your bike.
He'll need this - a Specialised Globe.
And a Carradice Kelbrook bag for carrying your picnic lunch. They've been making bike bags for over 70 years.
And of course, to make sure he's on time for your date, a Rolex Explorer watch, as worn by Sir Edmund Hillary.