First bake a recipe for soft and chewy cookies of any type. I've done double chocolate and chocolate chip. Today I used this recipe that I found online and it worked perfectly. You can't just use any cookie recipe, because one that only makes small cookies (which might not scale) or crisp cookies (too brittle or crumbly to hold sticks) wouldn't work. When you take the cookies out of the oven, immediately skewer them gently with wooden barbecue skewers. Push the skewer all the way in, but not so far that it comes out the top. Put skewers in more cookies than you think you will need just in case some fall out or break when you're assembling the bouquet. (Don't ask how I learned that!) Then walk away and don't touch the cookies until they are perfectly cool.
While the cookies are cooling, prepare a container to hold the bouquet and some decorations for their packaging. I've used clean peanut butter jars in the past, just decorated with ribbon and fabric. A decorated yogurt container weighed down with uncooked rice would work nicely too. Today we used a container that actually came with a professional cookie bouquet we received after Worth's birth. It already has little holes for skewers. Dorothy decorated it with permanent markers. We also decorated little stickers to put on the outside of the cookies. I used round Avery inkjet labels, which I printed with little welcome home slogans, then let Dorothy decorate with the markers. In the past I've printed out simple labels with words in a flourishy font in a color to match the ribbons I use on the cookies and jar--simple and pretty.
After the cookies are completely cool, wrap each cookie individually with plastic wrap and tie it up with a ribbon. Cut off the bottoms of the skewers so the cookies are of various heights, then arrange them in your vessel. Stick the labels on the front of the cookies. Finally, stabilize the cookies by arranging tissue paper around them. I wish I could think of a better way to handle this last step than killing trees by using the tissue, but I can't. Only tissue paper (that I can think of) can be wadded up at the bottom and splayed out at the top to gently support the cookies all the way up.
Gift the bouquet, then enjoy the leftovers with milk! :)
I saved a couple skewered cookies by wrapping gently in foil and freezing. These individual cookie "pops" will make nice hostess or birthday gifts from Dorothy in the next couple weeks.