TL;DR - I very much dress for what makes me happy in that moment. I find clothes that make me feel as confident and happy as I want to be in that situation. Yes sometimes comfort goes out the window but in an event where I think I look good and am getting compliments would I like to swap it for something more comfy and less dramatic? No, I’m happy making that tradeoff. So yeah, generally I dress to express, sometimes I’m a bit extra with lower cut tops, more dramatic skirts, louder prints and loads of accessories and other times I’m wearing black with black with black from neck to feet but I never dress in a way that makes me unhappy. Generally it does tend to be on the more overt “feminine” side - dresses, skirt + top rather than jeans or leggings but that’s because I find that is what suits my figure best and makes me feel good!

I had literally had a conversation about this topic with some friends the other day, both men and women which really highlighted some of the more stereotypical relationships that people have with clothes by gender. And yes lots will be driven by societal pressure and expectations but I thought the things that came out of it were fascinating.

Generally the guys views on clothes were pretty simple. You have have tshirts, jeans, shorts for casual wear at home or generally with friends. You have some nicer shirts, maybe polos or casual button downs that go with either nicer (i.e. not worn out) jeans or chinos for smart casual or going out then you have the smart items for formal events, suits, white shirts, ties etc. Basically their relationship with clothes wasn't that of having "outfits" but a selection of things that could be sorted into individual "buckets" for the formality of event - realistically 3.5 levels of formality with some overlap and the items are very much mix and match - any colour shirt goes with any colour trousers (unless explicitly dressed by their wives).

On the other hand the women had a much more shared understanding of clothes being significantly more fluid. Like what you might wear to a casual event very much depends on location, time of day, itinerary of the day, relationship to attendees, whether you are focus of attention or a background character, matching the level of friends, weather and even just how you feel that day - is this a day you want to be seen or a day or one where you want to vanish? Even meeting up with a friend can vary where it feels like there is pressure to match the energy that friend typically gives off so you may over or under dress for it. Of course women's clothing has a lot more variation in items where what is socially acceptable most of the time for men is a little more limited.

It was rather funny seeing a lot of mutual understanding with the women when talking about clothes but earnest confusion (and interest) from the men. One of the biggest differences was that the women view clothes as fun, something which the guys had never really considered. That dressing up or finding something new and showing it off and otherwise expressing yourself can be actually be enjoyable. Sure, sometimes it can feel like there is a lot more pressure and that can sometimes be a lot when you feel obligated to look good whilst not feeling your best but I think the idea of having fun with your appearance and expression is one of the joys of being a woman. The elation of giving and being given compliments on the elements that have had effort put into is such a great feeling I wish everyone could have.

And no, I'm not saying everyone feels this way or even has to, the subjects of this social information gathering was 5 straight white cis men and 4 cis straight women in their mid 30s. I know cis gay guys who love to express themselves and I know trans guys who still have a healthy relationship with clothes even if they tend towards a more muted outward expression. And I know the opposites in both of those categories. And I know women who don't enjoy it and feel a strong pressure to appear a certain way even if they don't want to.

And with the majority of my TED talk over to answer the original question - I very much dress for what makes me happy in that moment. I find clothes that make me feel as confident and happy as I want to be in that situation. Yes sometimes comfort goes out the window but in an event where I think I look good and am getting compliments would I like to swap it for something more comfy and less dramatic? No, I'm happy making that tradeoff. So yeah, generally I dress to express, sometimes I'm a bit extra with lower cut tops, more dramatic skirts, louder prints and loads of accessories and other times I'm wearing black with black with black from neck to feet but I never dress in a way that makes me unhappy. Generally it does tend to be on the more overt "feminine" side - dresses, skirt + top rather than jeans or leggings but that's because I find that is what suits my figure best and makes me feel good!