Reddit mentions of Men's Stylish Slim Fit Wool Pea Coat Winter Jacket (M, Navy)

Elegant, timeless, and classy, but with a dark edge?

That is basically my MO, too (though I am a similarly aged female).

My suggestion - find a fashion icon of sorts. Mine happens to be Daphne Guinness - she's regal, weird, and beautiful. Elegance without being cliche.

Some examples for men: Blixa Bargeld, Karl Lagerfeld, Marilyn Manson (when he is a little less shock rocky and more refined), etc. Also - I am living for the clothing/wardrobe decisions of the Meth's on Altered Carbon (just imagine this in black).

This is how I handle my wardrobe:

• Everything is black, gray, or olive drab (besides the aesthetic quality - this means that all of my clothes go together and can be partnered in endless variation).
  
• Purge things that don't fit well, or rather, you don't feel great in. Slowly replace the cheaper, ill-fitting items, with up-scale items.
  
• Don't be afraid of getting a higher end item tailored to fit you well. Pay the money, keep it forever.
  
• Buy what you like - but try to keep it to clean lines and no logos or prints. Suit jackets and winter jackets should be full length or hit mid-thigh for that upscale cyberpunk feel. Example 1, Example 2
  
• Trash any and all cheap jewerly or accessories. Skip spikes and chains (unless they are understated and minimal), and avoid shock value. Find items that are weird, morbid, whatever, but have them subtle - something that people from 30 feet away wouldn't look twice at, but up close they realize there is something more there.
  
• Purchase a handful of nice quality, simple/elegant accessories, a nice but unique watch, rings, or necklace or two. Again, it can be weird, or morbid, but try to avoid tacky, cheap, or colorful.
  
• Shoes - I recommend three pairs to start with: Nice pair of "dress" shoes - something you'd wear on a date or to a wedding: Example 1, Example 2, Example 3. A pair of athletic shoes - find some black trainers: Example 1, Example 2 (but even converse or vans would work), and something for the summer: Example 1, Example 2, Example 3.
  
• If you find something you really like (shirt, pants, whatever) - buy two or three of it. Buy it in Black, Gray, and Drab, if they have it, or just buy two in black. Stock up when you find "IT".
  
• You can still have some weird flare - sunglasses for instance. Example 1, Example 2
  
  Once you've mastered some of the above items - you can start adding items in. Be okay with a small curated wardrobe and build from there.
  
  Here are some links to some ideas:
  Clothing - POWHA
  
  Clothing - Zolnar
  
  Clothing - Jean Kutzarov
  
  Accessory - Scarf
  
  Jewelry - Raven Ranch
  
  Jewlery - Martha Rotten
  
  Jewelry - MRD
  
  Exquisite Corpse Boutique - custom timepieces, Jewelry, etc. This is a friend of mine. He makes custom pieces that are to die for (and affordable!). He made my wedding plugs.
  
  More inspiration - Juha Arvid Helminen
  
  Let me know if you need more examples, have questions, or need clarification. :)
  
  Edit: Just realized I didn't talk hair.
  Find a salon near you (not sure where you are - but look for quirky and younger - NOT a chain place if you can help it). It won't be cheap - but a nice haircut is worth it. I recommend going all black, except for a swath of platinum blonde (it isn't cheap to maintain) - but you can use this as your "party piece". Leaving it blond is great, but if you want to get crazy, you can occasionally shock it with some color (which bleeds out quickly).
  
  Something like this or this coupled with a stripe like this.
  
  If none of these are your hair type - describe it and I will try to find some better suggestions.