I feel guilty spending money

You deserve to enjoy nice things during the little free time you have. 

If this feeling follows you for a while, could be good to donate towards some causes you're passionate about (scholarships, charity, etc).

You work hard so you deserve to enjoy the money you make. I don’t think twice about the majority of what I buy

I kind of like spending money.

Plenty of us are like that, this is a normal feeling. While I no longer suffer from what one may call 'spending anxiety', there have been so many differences in the way I've spent money throughout my life that I am extremely diligent about where my money goes, from purchases big to small. 

For context, my family went from being very poor to very well-off during my eighteen years with them, primarily intensified by my folks' rigid sense of frugality, priority alignment, and keen financial senses. After I finished college and began my big-boy job(s), I ignored their profound advice and ultimately played life on hard mode for a bit - accumulated some debt, mismanaged funds, and suffered from substance/impulse control. Not a very ideal period, but taught me plenty. 

After I realized I needed to get my shit together, I spent 5-6 years erasing those prior 1-2. This was a monumental task, involving selling tons of things that I didn't need, downsizing current conditions, and being FORCED to grapple with one notion: get yourself out of the hole. I did not permit myself to eat out, go on trips, or have any kind of fun. I became obsessed with becoming financially stable and building back my credit score, focusing on that and nothing else. 

My point is this: both of those thought processes are flawed. Recklessly overspending without a sense of structure is bad, but abandoning any enjoyment of life completely is just as silly. I wasn't happy during those recovery years, and it was constantly filled with anxiety and stress. After I eliminated debt, accumulated a positive NW + cash flows, and hit that 800-marker on my credit score, I thought it'd be the end. But it wasn't; the goalposts kept being moved back in my mind, and I suffered from MASSIVE spending anxiety. 

Let's flash forward to now - I believe I've figured out the balance. In recent years, I've spent fuck-you money on things that I am passionate about, things that truly matter to me. I will always pay top-dollar models, trims, and all the jazz for shit that brings me joy - even if others scratch their heads. I can do this because I do not overspend on anything I don't need. I keep constant tabs on my money and investments, I know every single cash outflow I have (and will have), but I'm not so anal about penny-pinching that I'm going to let my quality of life decline. It's an ebb-and-flow game, and you don't have to go through all the shit that I did to figure out it. 

So, OP, I'll leave you with this - breathe a little, and just think about your priorities. What makes you happy? What will make you happy in the future? Test the waters there, and spend some money. See how you feel - if you like it, great! Keep it in moderation and allow yourself to live. If you're uncomfortable with it - no worries, don't panic sell everything. Just re-assess and mark it as a learning experience, knowing you'll continually evolve. Simultaneously, be realistic about your current responsibilities, knowing what you'll owe and when. Earmark your future financial outflows, but don't let them dominate your life now and fuck up your mental. It's easier said than done, but as is with everything: there is always a balance.

Hope this helps. If you'd like some advice on specifics, PMs are open. 

Always been odd to me to hear young white collar folks (bankers, lawyers etc) talk about their income & spending in the present tense.  e.g. “I make $xx” or “I can afford $xx expense on this salary.”

Nobody is being paid this amount for very long. Other than the 2-year analyst stint being quasi-guaranteed, the rest of the career is subject to constant change. So I’ve never really tied spending to what I “make” and honestly never even talk about earning in the present tense. There’s only what I’ve made.

Granted, with your education level, there will always be six-figure jobs available. But you may not want to do those. You may prefer, if you’ve saved enough, to do something else with your time.

So I think the only amount we really “make” is the amount we can make without working . . basically your savings times a conservative rate of return. You make that, and everything else you do is compensation for an indefinite time commitment on your part. May be helpful to think of jobs as projects.

If you think yourself too stingy and are looking to a message board for encouragement - I would suggest you try thinking about spending in future value terms.  

That $300 meal is actually $1800 in 2033 dollars (compounded at 20%).  You lose that train of thought very quickly.  Spend what you need, realize that long term enjoyment stems from experiences, and embrace deferred gratification in the knowledge that your money is working really hard for you.

If you make a lot of money you should enjoy it. If you're generally being reasonable don't second guess your discretionary spending if you're saving and investing properly 

Give it to me, I can spend it for you.

All joking aside, consider donating to a charity of your choice.

Depends. Is it a guilt from wanting to buy nice things? Or are you trying to buy nice things but dont have the desire to?

You are in your early 20s it sounds like so IMO you dont know yourself as well as you think yet, which means there is plenty to discover. Try picking up different various hobbies and interests (might be hard with amount of free time you have). Once you find a few passions you love then you can prioritize spending money on things that actually matter to you, instead of having no real interests to speak of and just buying status symbols.

If you cant find purpose for your dollars yourself then some marketing department out there will. Make that decision for you. 

Personal example: If you told me in college I would ever spend as much as I have on a road bike then I would have laughed in your face. But it's something I have picked up and discovered in my 20s, and I love it. Great exercise, to explore outdoors, networking, competing in race events, etc. Alternatively, I drive a japanese shit box and havent had a car payment in a decade but am not a car person so dont really care to spend money there (The resell value of my bike is higher than my car).

But if I had no interests outside of work and TV, leading to feeling bad / insecure about myself, then man those Audi commercials would seem a lot more appealing

Do what I do.  Spend the money on things that make more money.  I buy small busineses, real estate, etc. with my cashflows.  I feel the same way you do about spending money on unnecessary improvements of things.  So now I am just plowing that money into small busineses to hire more people.