Help me out people. Im about to step off a plane in Madrid by myself with uncertainty of where to stay. Though ive done my research, will i have a problem walking up to hostels in madrid?

My guess is no, it's no longer summer here..
If you are uncomfortable about approaching a hostal or hotel, there's normally a booking service at the airport or at Atocha rail station...
One hostal which I think should accommodate you no problem, so long as you can speak a little Spanish (cheap, clean but v. basic) is Hostal Peralta, Calle Arenal 24. THere are other hostals close by if fully booked. I'm sure tho that any of the hostals on Madridman's site will be able to direct you to another if they are fully booked.
Have a pleasant stay

Most often with hostels (called "hostales" in Spanish or "hostals" in Catalán) they'll have a button at the "portal" or doorway which you can buzz and the owner will call down to see who it is. Just ask, "¿Hay habitaciones?" (Are there any rooms available?) and they'll either say "Sí. Sube" (Yes, come up") and they'll buzz you in the front door and then you'll go up one or two (or three) flights of stairs where they'll receive you. OR you'll buzz the button and they may say "No. Está completo" (No. We're full).

Whatever you decide, I recommend visiting a number their websites of those in areas you're considering and at least then you'll have an idea of where they are, their prices, and how it looks on the inside before you even get there. This can save you A LOT of time. Check out the MadridMan list HERE of 100+ hostels in Madrid.

If your first night there is the Thursday the 30th, TOMORROW NIGHT (maybe this message is too late for you), you'll probably be fine but it's more difficult to find a room over the weekend. In fact, you may find one with a room available for Thursday night but that same hostel may be full over the weekend so you MAY have to move to another one. Wow.. good luck.

Saludos, MadridMan