For me it’s all about dressing for the weather, not the season, and living in a place that is warmer and often finding ourselves feeling like it's not a specific season, I look to key pieces that I can style not only now, but later on. I also gravitate towards what really suits my style rather than focusing on the latest trend.
While most will only look at this dress, solely as a Summer number, I also see it working perfectly for the cooler months. Styling it with black tights, and a wool knit turtle neck (long or short sleeve) underneath; paired with a black coat and shoes (type determined by the occasion). The key is picking out pieces that you really love but have multiple styling options, and thanks to online shopping we also all have more options globally. Plus, it will also give you more of an incentive on purchasing investment pieces, because you will get more wear out of them, making them look different each time.
Oh, and we have to talk about finding a dress that has lots of detail and pleats, while also having nautical stripes... clearly, this belongs in my closet!!!