Growing a human takes a long time! I am currently at the end of growing my third and feel like I have been pregnant in every season and for a very (very) long time.
I don't think there is a perfect time of year to be more or less pregnant and of course it totally depends on the individual woman, both in terms of what they do and how their body takes to pregnancy. Both Summer and Winter come with their own challenges, advantages and disadvantages.
But Summer is approaching and with it comes things like holidays, weddings and festivals as well as life, work and everyday life. All things that pregnant women partake in, while wearing clothes.
Dresses are great things to wear while you are pregnant in the summer, mainly because they are so comfortable and will keep you cool (many women struggle with getting hot). This pregnancy i've really hated waistbands especially at the beginning and end for some reason - so i've defiantely embraced the dress.
I think it is worth investing in dresses that you can breastfeed in afterwards or that you can wear once the bump is going down/gone. The advantages of wearing an official maternity dress is that they are cut especially to fit over a big belly so there won't be so much pull and the hem line should stay straight, however many non-maternity dresses still work well.
With maternity dressing generally I think it is important not to deviate from your usual style too much. There is so much change with your body anyway the last thing you should feel the need to do is change your image too.
If you usually wear shorts and skirts invest in maternity versions. You may also find that you can wear many of your existing tops - which if they become too short you can layer with a vest underneath or with a belly band.
Plus you will most probably be wearing these for a few months post birth and if you are short of money look out for them on second hand sites or sell them afterwards.
Shirts are another great bump proof item of clothing - they look smart and are perfect for breastfeeding in afterwards. This one also comes in a non-maternity cut - the main difference is that the shirt is longer and wider around the waist - which for many is a more flattering cut anyway. It is also very soft against you skin and washable - something that once you are a mum things have to be.