Viva, I love the look of the J-Crew gingham trench, but if I was buying one, I would get a Hobbs or Burberry - a serious, can be worn anywhere, trench. The J-Crew looks more like a fashion trench, especially as you can get the matching skirt. I have two beautiful fashion trenches and rarely wear them.
My old (12 year old) black Burberry cropped trench gets thrashed every year from April to October and I live in sunny Australia. It is an essential travel companion whenever I venture anywhere north of the equator. Dollars per wear, that trench is down in the cents because it has been worn so much and given the quality fabric, construction and classic design, I am confident that I will still be wearing it in another 12 years. A good trench is hard to beat in terms of being practical. Which is why I would prefer to spend more money on this purchase than I do on occasion wear that is rarely used.