Woman with Shopping

Building a Wardrobe for Transwomen

Hey lovelies, I haven’t been very well this past month. There have been several lurgies doing the rounds of the office and as soon as I’d started to shift one, the next would be taking up residence. It hasn’t helped that I’ve been trying to save for travel and clear my debts so I couldn’t afford to take time off. So to get back into blogging and to cover while I sort out photographing the outfits, I thought I would do a more general style post.

A couple of years I ago I wrote a post called How to dress if you are starting out as a Transgender Woman. Well I thought I would produce a new version based on my experience after 2 years of being full time. This time I’ll try to be a bit more practical with my advice.

Again a disclaimer. I’m not saying there is a right or wrong way when it comes to style. For this post I’m just trying to concentrate on basics that you can build on from and develop your own style.


Woman with Shopping



So you are preparing to come out as a trans woman, you are still nervous and are worried about what people think.  Well you have a few very good options these days.

Online Ordering

Probably the best things for the new trans woman is online shopping. You can browse at your leisure and try on at home. If privacy at home is a concern then many retailers give the option to have the item shipped to a convenience store or locker for collection. The staff won’t know what’s inside and if the package is branded then they probably think it’s a gift.

Parcel Graphic

I would recommend a website with a good returns policy. Many will provide a prepaid label in the packaging for you to drop off at a Post Office or local store with no questions asked.


I wouldn’t entirely discount brick and mortar stores either. Long Tall Sally stores are usually very welcoming. Some have even offered special events for trans women (usually around prides). Outside of the more specialist stores, something to remember is that for most shop staff a sale is a sale. As long as you are buying something they should assist you.


Sizing is a nightmare for cisgender women so as a transwoman you will need to become familiar with the sizing charts for the various stores. You will probably find that you are a mixture of sizes to start with as each store seems to have a different idea of what a size is. Initially I’d get an item in a couple of sizes and return the ones that don’t fit. This is where the returns policy comes in handy.

Things to Avoid

To begin with I’d avoid stiletto heels. Even I’m still not 100% stable in them. Something also to be mindful of is how tight things fit. An ultra tight top will probably ride up for example or may be unflattering.


My Picks

I’ve picked out a few items from a few sites that I regularly use.


When it comes to tops, I’d look for something in the tall ranges. The extra length is more flattering. Without the extra length you could end up with a crop top!


Here I’d avoid short skirts to begin with (or at least wear them with leggings). You can go shorter as you get more confident, but you want to avoid anything riding up too much.



I’ve chosen a few basics, nothing too showy. Again the idea is once you have the basics you can build on from there. Yes I know I own all the boots, learn from my mistakes!

I hope this little primer was of some help. For my trans readers; do you have any advice to pass on to the newbies? Did you many any tragic mistakes? And for my cisgender readers; what tips would you pass on?



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