It really depends on how much you care what other people think, and your honest assessment of how old you look. I'm commonly mistaken for much younger so I still often wear outfits that would normally not be considered age-appropriate, but I do care about blending in fashionwise in different situations.
I personally don't wear strapless dresses because I hate pulling them up because they inevitably ride down, so I wear spaghetti straps in the summer at the very least. With that silhouette the width of your hips isn't visible so it's possible to wear the dress without being read as masculine.
