Some questions I received by email the other day:
"Making the transition to modest attire: how difficult was this for you, from a social perspective? How long before they got used to the idea? Did you lose any friends over this issue? What type of responses did you get from family and friends? Is it fairly simple to find modest attire in Israel? Any suggestions for making the transition for others? And do all observant Jewish women in Israel wear dresses/skirts only?"
I certainly got all sorts of reactions about my transition to modest attire. I can't say how long it actually took before people who knew me stopped giving me those weird looks, but I estimate it took at least a year. Also, the transition wasn't done all at once. For example one summer I stopped wearing sleeveless tops, and next summer I gave up on short sleeves as well and started wearing only skirts. Then I also started paying more attention to my neckline.
I can't say I actually lost friends because I started to dress differently. My true friends remain as close as before, despite our differences. However, there were people (both family and friends) who didn't hesitate to say all sorts of revolting things, for example, "what are you going to wear to N's birthday party? Some ugly shapeless rag again?". I must say I never, never expressed my opinion in the way of, "hey, look at me, I'm not wearing pants anymore because I think that's immodest! And that makes me better than you". No. I simply started dressing according to my current preferences. It was enough to attract negative reactions.
In Israel, it's relatively simple to find modest clothes, because a large part of the population are religious Jews. No, not all observant Jewish women wear skirts; some wear pants and some don't cover their hair. However, the market is large. Of course, it also depends on where you look. For example Tel Aviv might not be exactly what you'd call a modestynik's paradise. But in Jerusalem or Bnei Brak there's an abundance of shops with beautiful and modest clothes and hair coverings. I'm aware of the fact that there are areas where modest clothes are almost impossible to come by, in which cases you might want to turn to more creative options, such as browsing second-hand shops, ordering online, or custom-making your clothes.
As to suggestions for the beginner modestynik, I say: start with what you have and work with it. Most likely you will need a big shopping trip, but you can also make use of what you have in your closet. I still have some sleeveless tops and low-cut shirts from my pre-modesty era, which I successfully utilized by wearing layers (one shirt on top of the other). If you have a see-through skirt, you could wear it over another skirt for an extra hip look. If you have a dose of creativity in you, you could even try to make skirts out of pants. I haven't tried that, but I've heard smashing success stories!
Also, don't be too hard on yourself. It's alright not to do everything at once, and it's alright to take one small step at a time. For example, one month you may want to stop wearing shirts that don't cover your midriff, and next month you can decide that from now on you're also going to pay more attention to how tight your clothes are. As long as you remain focused on your final goal, nothing is out of reach!