"Why do people persist in trying to go to places which have a specific purpose or theme, and not fit into that purpose or theme?"
Well, first of all, there are those who don't care for dress codes. Like, at all. They dress like they always dress, and they seem to completely ignore their surroundings. Same reason why they insist in walking around snow-covered Christmas sims in skimpy micro-minidresses and 6" platform sandals with 12" spike heels or on subtropical beaches clad in black biker leather from head to toe like a one-percenter. Anything to not reduce their sexiness or badassitude.
Or it's simply their style which is the more likely, the more unusual it is.
I think some intentionally break dress codes to demonstrate how utterly they despise role-playing in any shape or form.
I also know someone who is too much of an anarchist to let anyone tell him what to wear. That is, even he puts on a tuxedo when appropriate. And he doesn't Hypergrid often anyway.
Then there are those who don't know that there is a dress code in the first place. Some go to OSW and look up which sims are busy without checking a) what that sim is and b) what's happening there. Others don't know the OSW website and believe the OSW beacons are nothing more than nifty Hypergrid teleporters. They seek out the busiest sim and teleport there to meet people. But the beacon doesn't tell them anything about on-going events either, not even about the sims except for whether they're Adult-rated.
At events that encourage or require nudity, there are those who a) are too prudish or too badass to strip down and b) couldn't possibly imagine for the life of them that anyone else actually would. At least not until they arrive there. After five minutes of waiting in vain for the clothes on the female avatars to rez, or after 30 seconds when the dicks on the male avatars have rezzed, they often nope out again anyway, so they aren't much of a problem.
Not being able to dress in a certain way because there's no fitting clothing of that kind for your body doesn't play such a big role. If I can't dress appropriately for an occasion, and I usually can't, then I don't go there, plain and simple.
I even refused to go to beaches for quite a while unless they were nude beaches. The reason: I have a Roth2 v2. There is absolutely no mesh beachwear that fits on this body. And layer swim shorts look ridiculous on me without a bulge. In fact, I had absolutely nothing I could credibly wear on a beach. I only started to go to non-nude beaches after I'd managed to re-texture some sculpty bulges for some layer swim shorts. Before then, I always sent Juno because layer swimwear looks better on her.
I think this only becomes an issue if you attend an event although you neither want to nor really can, but you have to because you were invited by someone who insists in your presence. For example, if someone absolutely wants you to attend the opening party of their fetish sim, dress code is latex, full stop, but you've got a Ruth 2.0 for which no latex clothes exist, and you refuse to wear stolen Athena clothes which may not even fit properly anyway. Then you can choose between coming as you are and breaking the dress code, coming naked which you think is sexy enough and still breaking the dress code or letting your sim owner friend down by not coming at all.
Now, this goes for single sims and mostly for specific events on those sims.
An entire grid with a specific dress code has to be monothematic and therefore tiny with no third-party sims whatsoever. I don't know any such grid from the top of my head. Even Littlefield isn't all about BDSM and doesn't require fetish outfits everywhere.
Okay, now let's imagine a hypothetic medium-small grid that's all about glitz and glam and showing off. Where everyone has a Lamborghini Veneno, of which only three were made IRL, as a daily driver. Two dozen sims dedicated to this in various ways. It's actually grid-wide dress code.
But there's one sim on that same grid where someone offers self-made, therefore legal, freebies. Let's suppose they're actually quite useful clothes for legal, made-in-OpenSim-for-OpenSim mesh bodies of a kind and in a quality that you can't find anywhere else, also because they're no-transfer exclusives. In other words, exactly what Juno and I need.
That sim is in that grid because the sim owner is friends with the grid owner, the previous grid which hosted that sim had gone down, the sim needed a new home ASAP, and the grid owner owed the sim owner one.
However, none of us can dress in the style required for the grid. There are no legal clothes for that theme that could possibly be worn on Roth2 v2, there are no legal clothes for that theme that could possibly be worn on Ruth2 v4, and both of us refuse to switch to stolen bodies with stolen heads, stolen skins, stolen hair, stolen clothes and stolen shoes just for that sim.
The only chance we'd have if we don't want to pass on that content, and we don't, is to sneak into the grid when there's nobody else online and hope that our mesh bodies and our clothes are too obscure for the grid server to have them blacklisted for not being glamourous enough.
Or a variant on this: Imagine a grid whose owner has openly stated that Athena Petite is an underage body, full stop, and therefore banned on their entire grid, full stop, because allegedly, everyone who uses this body is a paedo.
Now imagine you've got an avatar based on Athena Petite because you find Athena's boobs too unnaturally big, and you wanted your avatar to be more realistic and believable. You've actually managed to make your avatar look like a realistic, fully grown-up real-life woman. No doubt that your avatar is definitely not underage. Maybe even to the point that people say you dress like a grandma.
Okay, now imagine you absolutely have to go to that grid. There's a sim that offers exclusive content which you absolutely need, or your best friend is going to get married on that very grid, or your favourite weekly event has moved into this very grid, or whatever.
What'd you do? Pass on that content/your best friend's wedding because your presence is not tolerated on the grid because your avatar is allegedly a kid because it's an Athena Petite? Go anyway, just to let yourself be perma-banned? Pester your friend to get married elsewhere?
Throw your principles and the general look of your avatar overboard, get yourself a regular Athena and increase your boobs six-fold just to survive a trip to that grid?
If that isn't relatable enough, we could try another required dress code for a whole grid: business attire. For female avatars, this means: Blazer jacket. Pencil skirt. No bare legs, nylon is an absolute requirement. Medium heels, no flats, no high heels. Spoiler: That's actually doable with an Athena, but very difficult. In fact, it's easier with a Ruth2 v4 and 100% legal clothing, especially if you know how to make your own alpha masks (or you could ask, and you may get what you need).
Again, you absolutely need to go to that grid. What'd you do? Break the dress code, stay out or go insane trying to piece the required look together that you may think won't even look good on you?
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