When I was 14 and wanted to learn guitar my mom took me to a pawn shop to get my first guitar. I knew absolutely nothing about guitars and picked the one in our price range that looked cool. It was an electric so we also got a small practice amp. I couldn't tell you what the guitar was, but I do know that it wasn't very good. I practiced with it and wrote some pretty kick ass ska songs on it. I brought the guitar to my high school band mates and they told me to smash my shitty guitar and handed me another.
If you want to be taken seriously you have to have a serious sound. You're not going to get this sound from a pawn shop knock off guitar run through a $20 distortion pedal and a $50 amp.
The first investment you should be making in your career is decent gear - not clothes. It doesn't need to be super pro just yet if you can't afford it, but do your research and get something fairly inexpensive that still sounds good. When you're just starting off you most likely won't know the best guitar or distortion pedal or amp or kick drum, but look it up. There are ample resources you can find on Google that give you reviews on pretty much every piece of gear on the market. +Does This Mustache Make My Ass Look Fat?
Your number one priority from day one is to sound great. This begins with practicing your ass off, rehearsing with your band until you could play the songs in your sleep and continues with getting the gear that represents the sound you feel you deserve to have. You're investing in your career. Some people invest in their careers by going to college and employers respect this investment because it shows that these people are serious enough about their careers to make this investment. Is your music career that important? Are you willing to make that investment? Are you that serious about your career?
My backup guitar which I have no problem performing with is a $600 Segal acoustic/electric. It sounds just fine. My main guitar (my baby) is a $2,000 Taylor, but I didn't have a Taylor from day one. My first acoustic guitar was a $300 Takamine I got from Ebay. I did research on it before I bought it and found mostly positive reviews and it was listed as a much higher price everywhere else so I got it.
When I go to shows the first thing I notice is not their gear, boots or hair style it's the sound. If someone gets on stage and plays a guitar that sounds like crap then I'll take notice of what guitar, amp and (if I can) pedals they're using. Most people won't think "man he should really ditch the Squire for a Strat and invest in an analog delay because this delay sounds so fake. And don't get me started on the digital distortion! Why didn't he just get an OCD pedal?!" Music freaks will think this. Everyone else will just think "Eee these guys don't sound so good" and won't really know why.
But at the same time I say this, pretty much every middle aged cover band has AMAZING gear and sounds like poop. They use their day job money to buy "the drum kit that everyone on MTV plays" - completely dating themselves in so many ways. You can buy quality gear but you can't buy talent. So no matter how good your gear is, if you don't have the chops it doesn't matter. You can't polish a turd. Even with "MTV quality gear." +Free Bird (Covers vs. Originals)