Flat footwear with midi/maxi skirts?

[LeeMiller]

I really like the look of flowing/a-line long/midi skirts (Pics to show what I mean) and have my eye on a couple but I'm not sure how to style them without a massive heel to avoid frumpiness?

Do trainers and tights look weird? Chelsea boots? DMs? Would a midi or a longer skirt look better with flats (I am petite)? I love them with 70s-style stacked-heel boots but it's just not a practical everyday look for me.

I usually wear a pair of DMs (specifically these ones www.drmartens.com/ca/en_ca/p/24116019 - can't find on the UK site ATM though. I buy the kids ones in size 5 cos they're cheaper than the adult ones and much more comfy!)
I have a pair of pink DM shoes though and haven't been quite brave enough to wear them with a skirt (www.tinfishshoes.co.uk/dr-martens-1461-heart-shoe-pink.html - Got them in the Dr Martens sale a few weeks ago for £30! Bargain!)
When I'm really playing it safe though I wear over the knee suede ones. Got a pair for £18 in Primark. Do the job rightly!!

CountFosco yes they seem to switch to their winter wardrobes based on the date not the temperature. I am usually the one sticking out like a sore thumb in bare legs come autumn but its turned chilly and I am too feeble for cold but stylish ankles.

FirenzeArno ooh I would fit in child-size DMs, thanks for the tip. £18 for over the knee suede ones is a bargain, I've seen some online at Zara and Topshop but not for such a good price.