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@Metalbro in another thread someone was able to fix this issue by cleaning the headphone jack and a cotton swab, can you please try? You may want to use a can of air-spray.
Reference: /t5/Xperia-XA-XA-Ultra/Xperia-XA-Headphones-are-not-recongnized/m-p/1211880#M5857
Hi @Metalbro, sorry to hear about this. 
Based on the troubleshooting you have already done with the great help from @YoGem, this sounds like it's related to hardware rather than software since it occurs with more than 1 headset/headphones.
What you can try and do is clearing data for the Smart Connect application in your phone, this is an app that handles connected headset/headphones and so forth.
To do this, go to Settings > Apps > Smart Connect > Storage > Clear data > OK. Restart your phone and plug in your headset/headphones again, is there any change?
If you experience the same behaviour try performing a software repair using Xperia Companion. This will delete all data stored on the internal storage of your phone and the latest available software will be reinstalled, that way we can rule out that the software in your phone is the cause of this.
Since data is being deleted it's always advised to perform a backup using Xperia Companion prior to starting with the repair process.
Let us know how it goes!
Hi again!
Oh, sorry to hear about your computer. 
Do you have the possibility to borrow a computer from a friend, colleague or family member or if you can visit anyone with a computer and perform the software repair that way?
If you don't have either possibility, I'd recommend that you get in touch with your Local support team so they can arrange a repair for you so your phone can be examined at an authorized service centre.
They will also help you with any questions that you may have regarding warranty, local service routines and so forth.
Keep me posted!
Update on the issue, there is now no sound coming from the headphones at all and it seems to not be recognised, the port itself feels loose to my gut is telling me it is a hardware issue
Hi again, sorry for the late reply. 
I see. I'd still recommend that you try the software repair if you can get a hold of a computer since if this is the solution you won't have to send your phone to service.
If you can't get a hold of a computer, the phone will need to be examined by a trained technician at an authorized service centre and your Local support team will arrange a repair for you!
I hope that everything works out!