What is the best way to go about updating your wardrobe? I still have yet to really redo my wardrobe aside from a pair of jeans, a pair of jeggings and a shirt or two but would really like to try and start purging some of my guy clothes and start getting more comfortable with women's clothing and start another step of transition. I don't really understand the sizes and outfits and what not very well and unfortunately I don't really have any money to spend on new clothes or anything and don't have any sisters or cousins I can borrow from. What's a girl to do?

You would be surprised the great buys you can get at second hand or places like Goodwill. Name brand clothing at ridiculous prices. That is where I started and you can learn about sizes very easily by trying them on before purchasing. You will find you can get a pretty good wardrobe for the price of one or two outfits in a department store and the labels are the same. Since you have jeans and leggings just get some new tops right now. You can mix and match and create many different looks this easily. Check out your local bargain stores as they can be treasure troves for us financially challenged people. 

Do you own a sewing machine? You can turn a lot of unwanted clothing into stuff you want to wear really easily.

Hi Katie J 

I've done pretty well with Ebay and the Target sale racks.

Most clothing companies will have good size charts with measurements on their web pages.  Sizes depend on the clothing company, but if you measure yourself you'll get a pretty good idea of what size you are.  My issue is that I'm a 14-16 on top and a 10-12 on bottom.  So I mostly stick with separates, blouses and tops and skirts or jeans.

Sizing - try EVERYTHING on, sizes are not the same between brands, in fact, they're not the same within brands.
Money, clearance bins, op shops, set aside a small budget, even $10 a week could get you some great stuff.
Also invest in the basics, tanks, skirts, jeans, dresses.
Spend more on trans-seasonal clothes, buy a LBD asap.

Hi

There's a lot of decent enough and cheap clothing out there, both new and second hand.  It does help to go with someone to help and critique what you're trying, and yes, try on everything.