Heat 1 tablespoon of olive oil in a large (12-inch diameter) skillet over medium heat. Once hot, cook the bacon slices in batches by first laying about 4 to 5 slices in the hot oil, turning them regularly and adding more slices, one by one, as the first slices brown and shrink. Do this until all the slices are cooking. When crisp and browned to your desire, about 10 to 12 minutes, transfer bacon slices to a paper towel-lined plate. Drain all but 3 tablespoons of fat from the pan.
Add the garlic to the pan. Cook, stirring often with a wooden spoon until the edges of the garlic start to turn golden. Add the pine nuts and continue cooking, stirring, until both the garlic and pine nuts look golden and toasted, about 5 to 7 minutes Turn off the heat and with a slotted spoon, transfer the garlic and pine nuts to the paper towel-lined plate too.
In a large bowl, mix the red wine vinegar and honey with a whisk or fork until dissolved then add the shallot, season with salt and let sit for 5 minutes. Add the remaining 5 tablespoons olive oil and warm fat from the skillet. Season with salt and pepper, whisk again then add the romaine, chicories, fennel and oregano. Toss the greens very well with the vinaigrette.
To serve, top the salad with the crispy garlic and pine nuts then crumble the bacon over it.