Online shopping is a valuable resource to the crossdresser since it allows many of us to maintain a degree of anonymity. I started out buying clothing online for delivery or collection in store.
The problem with buying online is the massively increased risk of buying something that simply doesn't fit. As with makeup, I've wasted a fair bit of money buying badly-fitted items that I didn't even return.
Once you've got a basic idea of your sizing it's far easier to shop online with better consistency but you will still find yourself returning items on a regular basis. Even today I will do the majority of my shopping online or in male-mode.
In this respect, eBay has become an incredibly economical way of picking up some bargains and some of my most treasured possessions are second hand items that were picked up for a fraction of their original price.
Finding your size in women's clothes is a skill but it's not one that takes too long to develop. Most women will tell you that different brands will run with different fits and there are few ways of judging what will and won't work without experience.
Even as of now, the best I've managed to establish is that I generally run between a UK size 12 and 14. I've also worked out that Lipsy and AX Paris are brands that I tend to fit well. All this was achieved through trial and error.
Certain stores such as House of Fraser do have sizing guides where you can enter your vital statistics and the tool will give advice on what size to buy for which brand. However, these usually rely on you to provide an example of an existing dress (brand and size) that fits you well.
Specific stores and Brands
Online stores such as BooHoo, ASOS or even Tesco provided me with a lot of early purchases. Tesco was particularly useful because collecting and returning items could be done with relative ease.
However, if you are looking for a more serious item or a particular showstopping dress you will need to look further afield. Department stores such as Debenhams, House of Fraser etc. will stock a wide range of brands. The online selection at HoF is vast and covers a wide variety of styles.
Finding your style is up to you but a lot of us seem to gravitate towards bodycon dresses as a good starting number. With a longer torso than the average woman, tops are often too short and dresses don't sit well at the hip.
Shopping in store
Again here I can only speak from personal experience but if you are shopping in any of the larger, high street stores, you should expect to be treated with consideration and respect.
However, the fact remains that for many of us, the fear of being judged is prevalent and can hold us back. As of right now, roughly 20% of my clothing is bought in store but because I'm such a fan of bargains on eBay, I will still tend to buy online more than anything else.