Lessons Learned: Part II – Style


If, like I was as a kid, you’re not great with Roman numerals welcome to part eye eye 😉 Where were we? Oh yes, things learned along the way.

Finding your style

A key part of expressing who we are is how we dress. Even choosing not to be bothered about creating a certain look is, ironically, a decision.

When you’re on the Trans spectrum, clothing can be freeing, comfortable, joyful, oppressive, or, if you’re unlucky, just plain wrong. A lot of it comes down to context and there’s times when what’s okay one day, is not on another. Not just for us, but partners if we’re a relationship.

Finding out what works for you is a long game. The gap between what is stylish and what’s fashionable changes: growing or shrinking as we find new things, rediscover old classics, or remix to find new ways of putting things together. It doesn’t mean you need to stay with the tried and tested, as mixing things up or blurring the lines can really freshen things. Nor should we pursue fashion as somethings are perhaps best enjoyed in the moment and never worn again. Dare I say – dare! dare! 😉- if you like the look of something, and so long as it’s not on the wrong side of revealing, suit yourself.

As a good place to start, take a look at what people your own age are wearing, when/where they wear it, and how it works for them. I say people because this could just as easily apply to someone who’s female to male or male to female. Either of those folk could be part time, curious, or thinking of crossing over. Regardless of the destination, it all starts with learning. There was no guidebook handed to me as a young teen. I had to work out what was okay and what wasn’t. Ah, those awkward teenage years. Let’s move on quickly 😉

Remember I said when/where they wear it? This is because people are short, tall, dumpy, buff, chunky, athletic, young, middle aged, old, glam, stylish, classic, white, Black, Asian, butch, femme, andro, etc. Yet, when we stroll by the shops or see images of those modelling the clothes, it’s rare we see that level of diversity. It can be disheartening to swim through that medium in which you are not represented. It took me a long time to work out who vendors were pitching the clothes to and what their ideal was. Now, I try to ignore the images pushed at me, and think will that work for my shape?

It’s not that it’s wrong to find inspiration from magazines, adverts, or influencers: just be wary if they are not like you. There’s been many a time that I’ve seen a pretty dress or cute top, but when I’ve tried it on, it did nothing for me (hello cold shoulder tops and boat neck t-shirts). There’s something for everyone out there, but I think some styles work better on some people. Just because it trendy, it doesn’t mean you have to wear it.

Shortcuts: learning from others

There’s some brilliant style blogs out there: from high end to high street to making do: and they’re a good place to learn about your style and shape. It’s not so much about rules, but more about shortcuts: if I pick this style of dress, is this likely to look good on me?

As someone in their *cough* late 40s, finding great blogs such as Already Pretty, Not Dressed as Lamb, Midlife Chic, Gender Blender, 40 Plus Style, and others all help. If that blogger’s style is not yours, that’s fine but do take a look at their advice pages on the right skirt length, how to wear X, or what’s new this season.

If you see a post about basics or a capsule wardrobe (the latter comes up like clockwork. See also nautical colours for Spring 😉), do have a read. Certain styles can be mixed with others to create a new look, freshen an older one, or dressed up for a night out.

Also, use a search engine of your choice for advice articles. Questions like how to hide big shoulders as a woman or how to dress well in my 30s. Experiment with different phrasing and see where this takes you. Oh, ProTip: use In Private or Incognito Mode to avoid picking up loads of cookies during your search.


If you’ve any sage wisdom or experiences to share, the comment box is below.

L x


  1. If you want to avoid leaving a trail of cookies or other information such as your ISP spying on your IP traffic try and use the TOR browser.

      1. Since you ask, the answer is yes.

        You have to use DNS to resolve an IP address, the Tor browser will scrabble the DNS when the message leaves TOR, the result is that your ISP can not tell which sites you have visited.

        TOR also scrabbles the contents more effectively that HTTPS.

        If you don’t want to use TOR, then perhaps you may want to uses its search engine in your normal browser. Unlike Google and others https://duckduckgo.com/ does not store cookies, scan your interactions, report store what sites you have been looking at etc.
        Like everything else there is a choice to be had, Incognito Mode is a good place to start. 😉

        1. +1 for DuckDuckGo and, IMO, it works very nicely on an Android handset, so there’s more privacy than pumping everything through Google/Chime. Well, unless you also log into Facebook 🙂

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