You can live without guards for now. I still haven't got any 1500 miles after buying my roadie, although I'm starting to get annoyed and want some now.
It doesn't matter how confident you are. Roadies are another level and you need flat pedals pref with toe cage to start with for a couple hundred miles. Then replace them with SPD-SL pedals like most beginner riders do. I did that exact method.
£50-60 will get you a really good fitting helmet, just try them before you buy, I got lucky with mine but I'm going for a Kask Mojito next which is £95 so ill be going for a fit haha.
Get a short sleeve Jersey and a long sleeve base layer, this will cover you in most weather conditions except rain when you'll need a jacket. Bib shorts are better than normal shorts too, nicer fit.
I wear bib shorts and Jersey most days. Pop on the base layer if its a bit cold and then the jacket if it rains. Bib tights in winter and in extreme weather waterproof trousers tucked into some decent overshoes. Cost a small fortune so far but its worth it. The auction site is a good place for bin shorts. You can get a Jersey and bib shorts for £20 delivered from China & branded team sky or other teams, obv knock off but can't complain, the bib shorts are brilliant, so much better than my other shorts and trousers, until wiggle drop me some new gear tomorrow
Wiggle do bib shorts and bib tights and overshoes sub £15 each. Can't complain when you look at the savings over a year.