I've always know Dr. Martens as a brand a bit more meant for the alternative market, often with a little 'interesting twist'. In recent years, an increasingly smarter range of Dr. Martens is introduced. Just like one of the alltime favourites, the great 'light' 1460 Air Wave (with yellow/black tab), the brand is not only worn with cropped skinny jeans, but more and more in combination with a suit as well.
Dr. Martens shoes were developed during World War II, as Martens was a doctor that loved to ski during his leave of absence. Going downhill, he injured his ankle. He found regular army boots uncomfortable, so he designed a new shoe that is popular to this day and worn by many.
Nowadays, Dr. Martens has shoes from very dressed to light boots, and of course the famous heavy work boots. The Winchester 7-eye is a sophisticated shoe that is ideal for combining, both under a suit and with jeans - you are 'never under-dressed'.
And with the typical Air Wave it is almost like 'walking on clouds.' I notice little difference in comfort between this all-time favourite and, for example, the new Nike Roshe 2.
Do pay attention when ordering your Dr. Martens online, and make sure you selected the men's collection! Some models have both a men's and a women's model, and there are websites (such as Zalando) that mix the two up. A classic women's version of the 1460 boot is not much fun to wear for men. It is better just to try them out in a store or order them at drmartens.com directly.
A suit can be great, but in my leisure time I often prefer to wear a loose-fitting blazer. The classic blazers brands, such as Kenzo and Hugo Boss always suffice, but it is fun to mix it all up with a sportier blazer.
That hottie behind you on the tram perhaps is already wearing Zara, so also check out Drykorn. Although I did not know the brand, a colleague pointed it out to me. It is just a bit more unusual, and has some nice, always wearable blazers in this winter collection. The brand is surprisingly affordable, and always a safe option for the upcoming holidays.