I believe the Sony ones look good. But I'd rather give importance to comfort and sound quality. Ultimately the headphones will spend more time on head behind our ears.
Why is "cooler" a criteria? Even if people will answer, physical looks are even more subjective. Even if you get a consistent answer here you won't necessarily have people on the street wanting to high-five you in approval of your tastes, since they probably think this is waaaaaaaaaaaaay cooler, man.
If you mean cooler to wear ie in warm temperatures then the answer is as always PortaPro. The MDR100aap is the hottest sweatiest things I've had around my ears. Very nasty indeed.
If you mean cool in looks then the answer might still be the same, nothing looks much cooler than the Koss except maybe their scandinavian designed and Japanese made contemporary: the B&O Form 2.
Otherwise an other classic headphone the Sennheiser HD25, Their functionality, sound and build quality and ubiquitous professional use over the last 3 decades gives them infinitely more 'street cred' than any fashion phone.
Remember old, classic and timeless = cool.
The new is a passing fad that will be dated next year.
So me being me, I ended up buying both, the Sony are Over-Ear headphones so ears start to hurt after a while and the sound is not so good. The Senheiser HD2.30 are On-Ear headphones and are so light and so sexy and sounds very good too. The Senheisser's are boss ass headphones.
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