Do those shoes serve an orthopaedic function?

Image: winnond / FreeDigitalPhotos.netWhile I have found some excellent online blogs and guides to while away the hours between now and departure day (59 sleeps!) the one thing I’m still struggling with is travel “fashion”. Now, let me be clear from the get go – until I made a very excellent girly friend about 4 years ago, I was not well acquainted with the concept of a dress. So I’m not talking about high-fashion, catwalk-copying, might-be-spotted-for-ANTM fashion here. I’m talking about not looking like someone’s eccentric aunt, who paints abstract nudes and always has slightly crazy hair.

Backpacking through the wilderness is all very well and good, but what about those of us who plan to travel mainly through cities and towns. I’m thinking less backpacking, more extended city-break. In these instances those “interesting” (read “ugly”) mosquito-repelling, convertible trousers just won’t cut it! Sure, I need me some sensible walking shoes, but do they have to resemble steel-toe-capped boots? Absolutely, I need a rain jacket, but does it have to scream “adventure traveller” and not “chic city-dweller”?

Footwear is my most taxing concern. Being one of those lopsided individuals who requires special insoles and footwear that supports them, being fashionable is already a challenge. My trusty black pumps are perfect for a night out or a fancy dinner, but there’s no way I can wear them for any extended periods of walking. And if it wasn’t for Birkenstocks this entire post would be dedicated to whining about flip-flops! So my final decision rests on my day footwear. Do I strike for fashion and take my trusty Converse, totally transformable into “casual evening in pub” or “aren’t I cute in this little skirt”? Or do I strike for sense and take my walking shoes, totally untransformable into anything else?

I have already changed my mental “to pack” list several times, so it will be interesting to see which shoes win out in the end!

I’d love to hear what relatively trivial fashion dilemmas others have pre-occupied themselves with? And if anyone ended up walking around Thailand trying to restock on half their “leave behind” pile 30 mins after arriving!

Edit: 03 Aug
SBellatrolling through my local TK Maxx tonight I found the cutest pair of Merrells (Bella).  Now, I know they won’t be everyone’s idea of style, but I think they will look great with jeans, cargo pants and most importantly a denim skirt. Packing crisis averted!

Image: winnond /