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1. Know your priorities
What's more important to you? Celebrating your wedding anniversary on the same day (or close to) your dating anniversary, getting the venue of your dreams, or simply 'cause it's cheaper to have it during off-peak seasons? Ask yourself these questions, and you'll be able to pin down a rough ballpark, so you can begin planning.
2. Wet weather plans
Unlike countries with four seasons, there are only two periods in Singapore you have to take note of: the monsoon season (which occurs during mid-November to early March, and from June to September), and the rest of the year, especially if you're thinking of having a garden or outdoor wedding.
3. Know your public and school holidays
I've had friends who've had their weddings take place a few days just before the Chinese New Year or Christmas holidays, and they've ended up with a lesser number of guests than expected. The takeaway here: having your wedding on a public holiday or a long weekend may not be that good an idea, as your family and friends may have other prior parties or obligations to head to, or they may be overseas.
Likewise for school holidays. Unless you're a teacher and have no choice but to have your wedding then, most of your friends (who have school-going children) will most likely be overseas and unable to attend.
4. Peak season
March, May, June, July, September, November and December seem to be the more popular months for weddings in Singapore, as they are usually in between big festivals like Chinese New Year, Qing Ming, the Hungry Ghost Festival, Hari Raya Puasa and Deepavali. Do be prepared, as your venue of choice may not be available on your preferred date. You will also be less likely to score discounts or additional perks then.
5. Auspicious dates
For the Chinese, sometimes they set store by auspicious wedding dates, which are supposed to help bless the couple's union. See the dates for 2016, and 2017 here. For Malays, the period after Hari Raya Puasa is best, but we've heard from our Muslim friends, that weekends are generally preferred, as that's when most of their family and friends are able to make it. For Hindus, there are auspicious wedding dates Hindu couples should take note of, too. They can be found here, or you can consult the temple for dates.