thanks, remix4!
Your advice saved me tons of time!
Created my own skin and solved the problem.
There is a high number of Menu Widgets used together with Dynamic Widgets plugin so a different menu be shown on a certain set of pages (not very effective but that was what the client did). All Menu Widget’s stylesheets were loaded by Dynamic Widgets regardless menu used on a page or not and this bumped total number of stylesheets on a page to 30+ causing IE8 to ignore those that went after first 30.
Thank you for the great plugin, BTW!