Thanks for the suggestions guys!
I've narrowed it down to the following two headphones:
Sennheiser HD558 ($100)
- lacks sub bass
- smooth
Philips SHP9500 ($70)
- punchy bass
- forward
They both seem to be quite handsome, well-built, and comfortable. I'm not sure which to pick though. These will be my first pair of headphones. I will be listening to these at home using either my laptop (HP Pavilion with Beats Audio) or my phone (Nexus 5), both using Spotify Premium.
I used to have Shure SE215s but didn't find their sound to be a big upgrade to the cheaper IEMs I had (Philips SHE3590, Brainwavz Delta, JVC Marshmallows). They seemed bloated. I returned them and got the HiFiMAN RE-400s this past summer and I can honestly say that they have changed my life. The RE-400s had a level of clarity that I had never experienced before. They present vocals beautifully and have such a nice, clean presentation. These earphones are what got me hooked into this hobby and why I'm now on Head-Fi on a daily basis. It took some time for me to get acclimated to their sound, but once I recognized how special they are, I fell in love. However, I have been listening to a fair bit of electronic-based and rap/hip hop music lately (CHVRCHES, Purity Ring, Childish Gambino, Mura Masa, etc.) and the RE-400s were really missing the bass that makes these types of music sound right. This lead me to getting a pair of JVC FX40s, and after giving them some time to break-in, they sound really good. The bass on the FX40s is just about perfect in quantity for my tastes (maybe slightly too much) while remaining decently controlled and well-mannered. They also have some pretty sharp treble that I do like. It can admittedly be overbearing at times, but I am not particularly sensitive to the bright treble so it isn't a huge issue and I like the sense of air and space it adds. They are also are quite fast and have surprised me with their technical capability. It's cool to hear stable composure during fast, complex sections of certain tracks with little distortion. For a $15, they are good, but they did not wow me like the RE-400s did. Their V-shaped signature is fun and works well with what I've listened to as of late, but I wouldn't call them special. The mids are quite recessed and distant.
This is all just me getting my thoughts down really, so I'm going to continue.
I commute four days a week and try to workout around three days a week so my IEMs have me covered in those situations. At home however, I'm usually just chillin', playing CS:GO, browsing reddit and Head-Fi while listening to music of course. I am pretty set on open-back headhphones since I'm curious about their benefits (expansive soundstage, effortlessness, light, etc.) and don't need the benefits of closed headphones (isolation, low sound leakage, etc.) since they'll stay at home. I'm honestly leaning toward the HD558s since they're smoother, more laid-back signature seems to be a better fit for winding down after a long day of school and relaxing (I usually get home pretty late. Commuting ftl.). I am afraid that I will miss bass though and they are $30 more and I've beeng thinking about getting something like the FiiO E10K to get some exposure to aftermarket DACs and amps, which I've never had. Welp, I'm starting to get off track so I'll stop here.
Your guys' input is greatly appreciated!