it's a multi variables problem:
a given headphone will have physical properties, and different reasons as to why they roll off in the low end. some simply have poor seal and just by paying attention to placement, you can already get a significant improvement in the low end. the SRH440
https://www.innerfidelity.com/images/ShureSRH440.pdf seems to be one of those if you look at the various RAW measurements(grey lines). but you also can notice that even with the best seal, that headphone is still far from a bass heavy headphone.
the second relevant parameter for a given headphone will be how much distortions it will show in that area. if the readings on that PDF are correctly showing the headphone's behavior, we can assume that distortions in the low end will become noticeable if you push those frequencies really loud. which is something that could sound euphoric in some cases, but in general is not what we want to hear. we usually want more bass not more distortions.
and that leads us to the 30cent question, how loud would you plan to listen to music? if it's reasonable, then I see no reason why you couldn't get the low end boosted(or the rest attenuated, it's really the same thing once we remove the notion of output level). and if you want crazy low end rumble for loud bass head music, then with this specific headphone, you're likely to get a lot of crap added with the bass boost and it might just ruin your experience.
another potential issue with the idea of trying to get loud low end is that you need the amp to be able to provide the needed voltage. let's say you want +15dB boost at 30hz(if your EQ allows that much boost), that's likely to clip the signal on some songs, so you would first need to lower the digital gain to avoid clipping. so let's say you play it safe and lower the digital gain by 15dB to be absolutely sure that your EQ is never going to clip anything, you now need the amp to be able to provide the gain for your usual listening level, plus 15dB to compensate for that gain attenuation.
in most cases it won't be an issue if from the start you bought an amp with some headroom, but you can see how depending on the boost you require in the low end, the amp's maximum output can become relevant.
so unless you know what you're doing, or have the opportunity to just try and decide if you like the result, I wouldn't advise to get a headphone with weak bass and try to make it a bass head headphone. even if it works, there is probably a better headphone for the job somewhere. and as a very conservative rule of thumb, a roll off at the extreme low end or extreme high frequencies are not stuff you want to try to completely compensate with EQ if they're pretty significant. because those roll offs are very likely to exist because of a physical limitation for the headphone. so just feeding it a higher voltage is going to force it to do something it's already struggling to do, and the likely result will be rapid increase in distortions. the bigger the boost the more likely it is to really suck.
if it's just a moderate boost, then of course an EQ can do the trick. I have about +4dB boost on my hd650 in the low end, and +6dB on my ER4SR IEMs, and I really like what I'm hearing. but those are still pretty reasonable boosts and I'm a really quiet listener, so in the end with my boost applied, I still get fewer distos in the low end than what someone would measure at 90 or 100dB SPL. as I said at the start, a bunch of variables are involved and there is no one fit all answer. the headphone, your listening habits, the amp, how much boost you hope to get, they all matter.
