This is my first pair of Dr. Martens, and I absolutely love them. People compliment on it whenever I wear them with black outfit, in order to let this pair of awesome shoes stand out (and they do!)

The only problem I have with Doc Martens is their sizing. I wear a 5.5 in UK sizing, and I had to choose a 6 (which is HUGE; I could fit my thumb or more in the gap) or a 5 which would squish my toes. Eventually, I went for a size 6, and bought the comfort insole wearing either thick socks or two layers of cotton. It helped a lot and now the size 6 fits.

When you wear the boots, you'd at least need to wear thick hiking socks to break into them, else face the consequences of multiple blisters (wearing regular socks, I had a huge blister on my right heel which popped, and I couldn't wear anything but flip-flops for a week.)

In doubt with .5's , go up a size. Although (yes, they're leather) they'll loosen up someday, you won't be able to wear them for good periods of time. Boots are supposed to be "larger", anyway. Make sure they fit after getting the insoles and socks though; if they still don't work, that means the boots are too big for you and that you should go down a size.