At the times of my mother and grandmother, Kimono was to quickly wear by themselves just before leaving the house. However, now it's a common practice to hire a Kitsukeshi (着付師, professional Kimono dresser). Of course, there must be a lot of Kimono lovers who wear Kimono by themselvesa and I am not against it. The difficult part of dressing is the tightness of the strings and the belts, and if you dress by yourself, it's easy to control it.
I myself, prefer to hire a dresser when I wear a formal Kimono. I say this because professional dressers make Kimono fabric really crisp and I feel refreshed and new. Kitsukeshi, Chakusoushi (着装師), Otokoshi (男衆, male dresser for Maiko) are all different name, but in fact perform essentially the same role.
When a Maiko is dressed by hands of Otokoshi, Maiko does the front part while the Otokoshi does the rear part. When the Otokoshi is the one regularly hired by the Maiko, there will be a subtle relation between them to get the job done smoothly within less than ten minutes. If the Otokoshi is a different one, then sometimes the Maiko gets trouble. For example, the tightness of the knots alone, can influence her day. To avoid this situation, Maiko communicates with the Otokoshi in details during the session. That was also fun for me, anyway.
Kitsukeshi are taught that communication is the key other than the skills. I totally agree because wearing Kimono is regarded as very special event today.
Click here to see a Blog by a Former Maiko, "Do You Know?"