Sunny, me boy, I would strongly urge you to get some shirts/sweaters in royal or sapphire blue. Here’s a dress shirt , here’s a clear blue polo shirt , here are navy blue non-pleated trousers , here’s a multi-stripe (but mostly blue) oxford shirt (Only the color multi-stripe - the others are too loud or too pastel) , and here’s a navy blue heather turtleneck for starters. The heathers are particularly nice.
Based on your pics, the jewel tones will all work quite well with you, as will white or grey (particularly if you have a tan). And don’t neglect orchid/violet/lavender in casual shirts - those shades of slightly purple-ish blue will work very well on you. When fall rolls around again, they’ll have a fantastic selection of crew and vee-neck sweaters, many in the heathery shades that I think work better on most folks than the clear colors. Burgundy can’t help but be great on you, and the ruby reds and emerald greens will also fly quite well. Colors that wouldn’t work particularly well for you are the very light pastels, peach, aqua, beige, and many shades of brown/tan. None of these will look *bad * on you, but they won’t enhance your looks at all.
Hie thee to a good hair stylist, and pay attention to what s/he is doing while you’re there. From the pics it looks like your hair is like mine - fine and lacking body. A good hair stylist can work with that, and you can then usually risk going to a less expensive place for maintenance cuts. But do NOT go for a spike or crew cut; those looks would not suit your face or body type. You need a bit longer, softer look around your face, as do most people. If you wear glasses at all, stay away from the dark-rimmed horizontally oriented frames that have been fashionable over the past ten years for some incomprehensible reason (they look good on only a very few people). You would want rimless or very thin wire rims in an unobtrusive color. In metals, you should always wear silver, platinum, gun metal, pewter, etc, not gold or copper. Again, it’s not that the latter will look bad; it’s just that the grey metals will look much better.
My final advice is this: get your hair styled, and buy one pair of trousers and a single dress shirt. If you can bring yourself to wear it, a tie would be good too. (I happen to worship Paisley myself, but not everyone does). One outfit; that’s all you need. Then go out and meet some women. For this purpose, try to pick one who looks like she didn’t sleep in her clothing the night before - hopefully some woman who gives you a vague impression of elegance without suggesting that she would accept (let alone insist upon) $300 shoes or trendy designer labels. Once she’s dressed for the evening, she really shouldn’t be considering her appearance at all except when she hits the ladies room (“oh shit, I just ran a stocking” or “Damn! I broke a nail” don’t count unless she then obsesses about it for the rest of the evening).
Spill your soul - the truth, the whole truth, and nothing but the truth. Explain that you want help in building a real wardrobe now that you’re out of the Early Orange Crate stage of your life, and that her appearance suggested to you that she would be a good person to ask to go with you to shop. *Don’t * push it as a date; she would simply be doing you a favor. There’s probably not a well-dressed straight woman in the world who wouldn’t be half-way seduced by the prospect. But get her to go shopping with you a time or two before you actually make any moves - then if it goes sour, you’ll still have gotten the benefits. Psych studies have shown that the single best thing you can do to make someone like you better is to ask them for help in some area. Among other things, it’s a compliment of the highest order, since it is a tacit statement that you admire their competence in the area of interest.
So: one hair style, one nice outfit, and then sally forth to find the assistance you need. Don’t worry about fashion - the only reason other than warmth that clothing serves is to make you look better. The same with hairstyles. So often you see people of either sex who are wearing the style du jour, and it simply looks like utter hell on them. If you strive for a more classic style, you never have to worry about it.