Sorry for the inactivity for the past few weeks. I’ve been hella busy and still haven’t had time to do another photoshoot :( I guess I’ll just have to wait.

Until then though, I want to cover a topic that A LOT of people ask me about: What do I wear?

Now this is always a tricky question, as what works for me doesn’t necessarily work for everyone. So if you’re using this as a guide on what dresses you should wear please keep these three rules in mind.

1. Know your body shape

Some of us are boxes, some of us are triangles, and some of us are lucky enough to be hourglasses. Your body shape can make a lot of difference to what you can wear.

For example, I’m a box/triangle shape (somewhere in the middle), therefore I would have a hard time wearing a dress which is tight all over. Instead, I can wear something that hugs to my chest but flares out around the waist.

If you don’t know what shape you are, here’s a simple guide:

2. Know your measurements.

Have you ever been clothes shopping with a woman? You know why it takes so long? It’s not as simple as “I’m a size 12 so I’ll fit into this” no bloody chance. You have to know your chest size, waist size and hips size and even then a dress might still not fit you.

I recommend having a measuring tape handy when you’re doing online shopping, as most shops will have a chart you can compare to. If in doubt, go with a larger size rather than a smaller. A lot of the time you’ll find your hips and chest won’t be proportionate, match the dress to your hips/waist as you can always fill your chest up with breasts, but you can’t just suddenly lose your hips.

3. Don’t listen to me (at least not always).

Like I said earlier, it’s hard to tell what is best for people, especially when I can only see them through a picture. I can give advice, but I will never know your body as well as you do.

If you think I’m wrong about something and that you can wear something I’ve told you not to: do it. If I’ve warned you to stay away from a certain dress but you think you can pull it off: do it. If I say two styles don’t match and you shouldn’t mix them: just bloody do it.

You know your body better than I do, so take my advice but please please PLEASE take it with a pinch of salt.

Alright, onto the main course. I’m gonna show you three dresses/outfits I’ve done recently(ish) and why they do/don’t work.

One of my favourite dresses right now, quite simply because it suits my body shape. Having a box shape means I have need the dress to create some curves for me, so wearing a skater dress works here because the flared bottom half hides my lack of hips.

I’ve said this to pretty much everyone who’s asked me for advice and I’ll say it again here: if all else fails, wear a skater dress.

I am yet to meet someone who doesn’t look good in a skater dress. It doesn’t matter what body shape you are, they seem to suit everyone. They’re a very safe option so if you’re new to crossdressing and want a good start, go with a skater dress.

Now here’s a dress I borrowed from Moon. She is at least a size smaller than me (probably more) and definitely has a more feminine shape. So it’s not too hard to realise that this dress really doesn’t work for me.

“But it’s still a skater dress right? I thought you said skater dresses were a safe option?” Yeah, they are, but only if they fit. If you look closely enough between my arm and waist you’ll probably notice that the back of the dress isn’t zipped up. This means the dress losses it’s shape and becomes a bit distorted.

On top of that, it makes my shoulders look huge and despite being flared at the hips I still look box shaped. All-in-all, this a fantastic example of why you should always buy clothes that fit.

And the last example, which I like to call ‘The Wild Card’.

Here is an outfit which is tight at the hips, tight at the waist, tight at the chest and doesn’t cover much. Now if you remember my first two golden rules from earlier then you would realise that, in theory, this outfit should not work.

But it does.

Despite being everything that I shouldn’t be wearing, I still somehow manage to look good in this outfit. Partly because I’ve used my hair to hide my shoulders, and partly because it was a good day for my belly.

Regardless of why this works, all you need to know is sometimes an outfit will work when it shouldn’t. If it isn’t going to cost you anything to try an outfit that you don’t think will suit you, try it anyway! There have been dozens of dresses I didn’t think will work for me, but sometimes they do.

That’s all I’ve got for the time being. I also want to say thanks to everyone who responded to my Crossdressing Services post; I’ll be trying to put that into action soon enough.

If you have any questions about dresses/what to wear, don’t hesistate to message me on Tumblr (my ask box can always take more) or on Kik: Jessica_Blaise