Here's something I did. I was surrounded by people all day including girls and you'd be surprised how many people thought this was cool/wanted to take pictures with me/asked questions/gave me their phone numbers. I just kept cranking the machines back up & changing records, and people kept swarming & smiling.
Thought the town needed someone as DJ during a street fair so I went. There were more phonographs on the other side of the ferns. Had I been looking to catch up with girls this would've done the trick (and the cool brick-walled garden filled with ferns and '20s dance band records was already there.)
Confidence (which I kinda lacked then) and a dose of actually knowing what I was talking about helped. (I've been into phonographs and old records since I was 8.)
The advice about cool glasses--Generic helps. Round wire-rim glasses are hot right now esp. for an alternative look. I had a set of very nice cable-temple frames copying some from the 1910s and they actually are back in style again. Had some of the Ellipse frames by Gunnar Optiks (a round-frame gaming eyeglass which I wore for blue-light blocking) and that helped.
As for selecting your New Look--Choose quality. A polyester suit with wrinkles or a bonded-leather dress shoe with scuffs looks tawdry and sleazy. A pure linen jacket in an off-white color, or a pair of genuine leather boots, can wear some wrinkles or scuffs with pride. The necktie should be good or it should not be worn at all. (I have worn everything from knit ties to silk four-in-hands to a 19th-c. black cotton cravat & like all of them, but knitted ties are kinda badass.)
Hats are tough. Hats, more than anything else, convey connotations. I have a few very nice ones--Cost doesn't make them good. Good hats are good when they're a trifle unassuming, and when they look like part of you. A trilby hat has bad connotations now as the fedora of the greasy incel. Keep America beautiful & don't wear a cheap trilby. A real fedora has a wider brim--I have one, a "Temple" by Stetson in mink brown with a black band. I took the Stetson tag & the feather off the brim. Feathers on a felt hat always make me think of a character in a Richard Scarry picture-book. I also steamed it & reshaped it--it looks comfortably lived-in now instead of giving off an aggressive 1930s press corps vibe.
Same with summer hats. Panama hats are amazing if you can get the real deal. I didn't. I have a boater. It's an Olney from Luton, England; they've made pretty much the same hat since 1914 and in the Edwardian tradition it is heavy and a trifle unsightly but at least it doesn't look like something a barbershop quartet's lead tenor or a county-fair barker would wear. I only wear it & my Stetson with semiformals, & all the rest of the time I wear a Goorin Bros. eight-panel newsboy cap in forest green wool (great for motoring, walking, hunting and shooting, and more.)
The reason I am a proponent of hats--I think they are neat, and I think that your face may be more pleasant. Autism often has a light-sensitivity component & once I started wearing blue-light glasses (in a cool frame) and wearing hats I didn't have to scowl & squint at everyone. As I look VERY AGGRESSIVE most of the time, I am really happy to have the softening look of glasses & a hat. People don't associate scowls and squints with friendliness, they think of Dirty Harry. If I'm wearing a hat & a pair of round glasses, I can smile, and perhaps they think less of connotations of Dirty Harry and more of Harold Lloyd.
It's nearing winter and I suggest a camel's-hair overcoat or oilskins. Get them in any color other than black. Might I suggest woolen tweeds. Tweed is available in enough blended colors to be the last true generic fabric. When I wore broadcloth suitings, I got mistaken for a minister. When I went to tweeds people started being more relaxed around me. It's hard to be uptight around the guy who shows up in church literally wearing a hunting jacket.
"Pick a style that represents who you are" is only partial advice at best. Really what would be most successful would be "Make YOU so cool that it shows even in how you dress yourself." You want to dress like you.
This suffices for dress. More guy stuff shortly