There are many factors here on our sunny island nation that prevent us from really dressing up. Walk down Orchard Road on a typical day, and you will see t-shirts, bermudas, and tons and tons of flip-flops. I realised that this phenomena can be observed at almost all stages of the typical male Singaporeans life.
In secondary school, we wear t-shirts and bermudas and slippers. Moving on to junior college or polytechnic, we try out jeans, some dress shirts and the occasional ill-fitting suit during graduation night. Serving National Service, booking out from camp meant wearing the mandatory cap to (poorly) conceal our shaved heads and the highly obvious army-issued PT shoes worn with blue jeans. As you can see, growing up into adulthood here really hasn't done much to improve our sensibilities around fashion.
So then, what should we do to get out of this mire of "fashion-less-ness"? Well, I personally turn to the Internet (try http://thesartorialist.blogspot.com/ or our very own www.menshealth.com.sg/style-grooming) and various style guides (such as our October issue's Guide to Style) for inspiration and ideas on how to dress differently and fashionably. Do I actually think that scarves and multiple layers of clothing in our humid climate are practical? Of course not, but there is just something about looking at a well-put together outfit that makes me feel somewhat more hopeful and keeps me looking forward a possible way of dressing differently to work, or a night out on the town.
So whenever I see something nice in a magazine or on a website, it gives me some idea of what to buy next when I head out into the shops. For those of us who feel a little lost when it comes to deciding what to wear each day, or maybe you are just plain bored with your current wardrobe - go out and take a walk around the shops and say to yourself, "I WILL get something new for myself today." Anything will do, a new bag, shirt, tie, belt, anything... it's really about being able to be adventurous, and doing something to that effect. Only then can you truly break free from the monotony of your own "fashion sense" (which really isn't evolving is it?)
That's what I'd do anyway.