I'm the type of person that likes step-by-step lists when I'm learning to do something new. Unfortunately, this is rare in the spiritual realm where we are called to "walk in the Spirit". Each person's walk is unique and individual and there aren't any "one size fits all" strategies. However, when it comes to dressing ourselves modestly, I think this may offer some practical help. I'm sure you have much more to add. Feel free to do so in the comments!
Common Problems in Dressing Modestly:
1. I don't know what is modest.
Although I've heard men complain that we women "know what we're doing" when we dress inappropriately, I don't believe this is always the case. (It is sometimes, so honestly search your heart before God and have Him check your motives.) Sometimes we really don't know how our clothing affects men around us because they are so different than us. I think God has built a protection around us in three forms. Every woman should have at least one of these resources available and some of us have all three. If you are a single woman, ask your father. A father usually has your best interest in mind. If you are a married woman, ask your husband. He has a double interest involved: he loves you and he doesn't want other men attracted to you in the wrong way! If neither of these are available to you, ask a godly, older woman in your church. Choose one who exhibits modesty herself and truly has a heart for the Lord. On top of these people, first and foremost, pray, search the Word and see what God has to say to you personally.
2. I don't want to look frumpy and outdated.
Some have given modesty a bad connotation by defining it in this way, but I believe modest clothing can be stylish. I don't think Christian women should follow fads, nor do I think they should look to the fashion industry to plan their wardrobes for them. However, modest clothing can be beautiful, functional and up-to-date.
3. I can't afford to buy a new wardrobe.
This can be a concern if you are newly convicted about your current wardrobe being immodest. There are many things you can do. First of all, go through your closet and pull out items that are already modest. Surely you have a few! Then, look at the ones that aren't and see if you can do something to make them modest. For example, if a shirt is too low-cut or see-through, you could add a tank underneath to make it modest. Lastly, periodically look for new items that go with what you have that you can afford. Don't be afraid to look at thrift stores or discount stores. Modesty is important enough to invest in.
4. I can't find modest clothing anywhere.
I personally think this is an excuse. I'm sorry if that seems too harsh. If you needed water to live, you wouldn't sit around and whine and complain that you couldn't find any. You would search and do what you had to do to find it. Yes, modesty is that important to our spiritual life. Some of my favorite stores for modest clothing are Christopher and Banks and Dress Barn. If you can afford it, Ann Taylor and Coldwater Creek have nice things. I have found things even at WalMart or discount stores and especially at thrift stores. There are many online resources as well. Do a search for modest clothing. I'll include a few of my favorite web sites in the Link List on Saturday.
5. I don't want to be legalistic.
Legalism is doing extra-biblical things in order to get to Heaven. We are not being modest to earn our way into Heaven. We are endeavoring to be modest because we have Heaven within us and we want to represent it to a lost world. There is a serious disconnect between a woman who claims to love the Lord, yet is turning men away from Him by causing them to lust after her.
Our goal in being modest is to please the One Who gave His life for us. It's our love gift to Him.
6. I just don't think modesty is that important.
I've done my best to convince you that it is. I don't believe you can be a serious student of the Word and believe that modesty is not taught there. If one is not dedicated to pleasing the Lord, they won't see this as important. The specifics of modesty are between you and the Lord, but if you don't care about it at all, make sure you are truly a disciple of His.
Many blessings to you all!