This is in my interest as well. As a contract employee in the past I've never been able to exceed the standard and therefore I dont itemize. I feel like I spend more money looking for deductions and that's doesnt seem productive to me. This year may be different though.
I am not a tax expert, but contract income that is reported on a 1099 doesn't go into your Schedule A deductions, it goes into Schedule C. On Schedule C, there is no "exceeding the standard". You take your income, subtract your expenses, and that's what goes back onto your 1040, line 12.
As a part-time flight instructor and occassional contract pilot, I subtract every possible expense I can - NAFI membership, insurance, charts, Foreflight subscription, any specific training software or materials I might buy, recurrent training like IPCs or even just refresher flights, flight bags, headset, flashlights, you name it. Anything that is used in my business. Oshkosh is really a big trade show/conference, after all.
Now, if you also fly for personal reasons, you probably have to do some kind of a ratio for common-use stuff like a headset, for example. I do NOT bother to subtract "home office" costs, mostly because I think they'd be farily minor, a big headache, and there would be implications when I sell the house.
Again, I am not a tax expert.
(On edit, I see RSLeeds got me on the Schedule C issue.)