I have been using Dark Blue since the turn of the millennium. Hugo Dark Blue was, alongside Bogner Man EDT, my entry into the world of fragrances. Back then, without the internet (and influencers), I bought it for a hefty price at the perfume store, but now it is available in the second tier for around €20.
Dark Blue is not (anymore) a favorite for me, but I find it okay! I think it is often rated worse here than it is! (This often happens with Boss fragrances. "Suit wearers, Benz drivers, business students"... it seamlessly fits into the series of prejudices from the "8x4" and "G.BELLINI €4.99" users :-D Don't get me wrong; I have nothing against people who use inexpensive deodorant or fragrance, and not everyone has the cash to spare for fragrances over €50+)
I think you can wear the fragrance all year round and for all everyday conditions. The scent is not as heavy as some others in my collection, and as a "just for shopping" scent or similar, I still find it suitable. Also regarding longevity. For about 2-3 hour "events," it's quite okay. As a daytime fragrance, there are now other scents with significantly better performance.