If there is one thing that being obsessed with clothes gives you, it’s a good understanding of what works for your body and your style and what doesn’t. I can walk into Zara and leave in ten minutes with a full, entirely functional outfit. Faster, if there’s no queue. (Of course, this is only possible because I have a very standard body in a size that Zara caters to.) (And of course one is trying very hard NOT to walk into Zara for high-speed shopping sprees, but it’s just a more believable example than Gabriela Hearst.)

I do get things wrong sometimes, especially when I shop online – even if one does proper research, purchases may not work out, and I sometimes don’t. There was that time I bought a Loewe bag that doesn’t fit my phone, remember? I also have a pair of beautiful Remain Birger Christensen light blue leather trousers that are slightly too big for me and therefore mostly unworn. Not to mention the Balenciaga trainers that are gorgeous, but insanely heavy. What I wanted to talk about today, though, isn’t my shopping mistakes, but the other side of the coin.

Once you have found things that suit you, it’s easy to stick to these things – be it a jeans and blazer combo or a midi skirt and a knit or certain colours. If you stay loyal to your tried and true formulas, you are unlikely to make a style ‘mistake’: I find that concept problematic, but you know what I mean. You will feel comfortable and safe. You are, however, probably also depriving yourself of some unexpected pleasures. You will, quite rightly, extrapolate based on your previous experience and assume that some things will not look good or ‘right’ on you.

It was with this assumption that I tried Lilli Jahilo’s Candy Dress (it’s not the official name, just what I call it). I had admired it for a long time, I thought it had a super cool 80s vibe – glamorous, but lighthearted and a bit camp. I was also convinced that it would not look particualrly great on me: I suspected the cut wouldn’t be flattering for my body type and that I would lack the street cred I thought was required to make the dress work.

Still, because I liked it so much and it matched the idea I had for the upcoming shoot, I decided to give it a go anyway. I thought that if I can fit into the dress (there is only one, the original runway version), I’ll style it out, that we’d find a way with the fotographer to make it work visually. Lilli was kind enough to let me try the dress and borrow it for the blog, so this is what I did. And you know what? It was perfect. Not only did it fit like a glove (like a very tight glove, mind you, sitting down was a challenge), but it looked great, at least to my eyes. Before trying it on, I had felt slightly intimidated by the dress. As soon as I had it on, this disappeared. Wearing it felt completely different to what I had imagined.

You may disagree with me on whether this dress is a good match for my body and style. But this doesn’t negate my central point: despite decades of attentive clothes-wearing, I could not accurately predict how I would look and feel in that dress. I thought I knew what colours and cuts and vibes suited me (or at least made me feel that they did), but clearly, my list was incomplete.

This incident has reaffirmed my already pretty firm view that it’s a good idea to try on different things, at least occasionally. It’s likely that in most cases, you’ll be proved right and that lilac jumpsuit will indeed look horrendous on you. And it is a fully rational strategy to dismiss certain things automatically, because there is no way to try or buy it all. But if there is something you adore from afar, never give up on it before you have actually given it a go.

Dress by Lilli Jahilo, earrings by Tanel Veenre, sneakers by New Balance. Images Getter Raiend, makeup Grete Madisson, hair Natallia (at Helen Heinroos Hair). I also want to thank the Estonian War Museum for letting us shoot (hah!) on their premises and for being the loveliest hosts one could wish for.