As nasty subzero weather descends on Toronto in the middle of October, I'd say if you want swimsuit shots of yourself on the beach your timing is a little off. But any time of year or in any location certain types of wardrobe are going to look better depending on your skin complection and hair colour and the style of shot you've requested.
Like any professional photographer, I can always offer advice about what's going to work and what isn't so you're well prepared. The shot above for example would have looked much different (and would be less effective) if our subject had been wearing a light top instead of a dark one.