Any 14'ers nearby the cities I mentioned?
Keep in mind, I have no real hiking equipment. Just my phone, backpack, and a pair of sweats. Literally what I look like in that photo. Should I attempt a 14'er without real gear?
Most of the routes are non-technical, so yes all you need is a backpack, some food/water, and a rough idea of the trail direction and you'll be fine. You can find trail info online or grab a book if want to be super safe. "Colorado's Fourteeners" is a good reference book. The trails are clearly marked, and the peaks you'd be near are decently busy, so just follow other groups if you're unsure of a turn. Normally I'd advise against trusting others in the woods for directions, but the trails are pretty clearly marked and the peaks near where you'll be are popular, so it's hard to get lost.
Obviously if you have things like trekking poles and hiking shoes it makes life easier, but they aren't necessary. When I was last out there I saw a few guys running up the trails with only a water bottle, shorts, and running shoes. They said they were trying to run from the trailhead to the summit of all the 14ers. Pretty hardcore.
One catch, however, is you need to start out early - like 6am. You want to be off the top of the peak by 12-1pm because almost like clockwork there will be an afternoon storm rumbling through around that time. You want to try to be near the treeline when that occurs - being exposed when lighting comes through is a scary scenario. I'm not sure if that timing works for you for your trip, but if you can make it happen it will be worth it.
As for the peaks in the area, you've got Pikes near Colorado Springs and Longs near Boulder/Ft Collins. I haven't done either but Pikes is pretty famous (there's a road to the top) and Longs is very popular. There are also tons of 13ers and 12ers too - ask around the towns when you get there and I'm sure the locals will be more than happy to direct you to their favorite trailhead.
