I have since learned the value of cycling-specific clothes on a long bike tour, though this is not defeat. I’ve discovered that it’s possible to have the comfort of performance clothing and to keep it subtle.
Merino wool jerseys are great in heat or cold, moisture wicking, and odor resistant. Also, they can be worn more than once between washings, reducing how many tops you need to bring and won’t stink like polyester active wear will.
After the first year of touring, we upgraded from toe clips to SPD clipless pedals. SPD stands for Shimano Pedaling Dynamics and is a pedal and cleat system of the mountain bike variety. What makes them different from SPD-SL, the road biking system, is that the shoe has one point of attachment and the cleat is recessed in the shoe, making them easier to walk in.
Pulling a knit skirt over your bike shorts, pants or capris will hide the chamois liner (you can also find cycling skorts). Also, looser shorts with a chamois liner are available for men and women. In my experience, padded bottoms make for a comfy ride. There are fewer seams and less fabric to bunch and chafe. Also, your sit bones will thank you.
Braids are great for keeping long hair from becoming tangled and unmanageable.
You will also want clothes and shoes for off the bike. Bring something warm for cool evening and mornings. If there’s any chance of rain I bring a waterproof jacket, pants, and shoe covers. Don’t forget your bathing suit!
For trips longer than over the weekend, I hand wash my chamois and tops along the way, hanging them off my bike to dry as to always have something clean to wear.