Don't just keep pinning those street style looks, start re creating those looks with what you already have. I have read several articles on the habits of stylish people and they all named two habits, draw inspiration from other people and they plan their outfits ahead of time. If you haven't looked into using a virtual closet, you really should. It makes planning outfits easy and fun not to mention you don't have to do the ritual of trying on three things (or more). Just one important tip, only keep things that fit, are in good condition and that look good on you. Trust me it will make your life so much easier. 

Wool Fedora by Rag & Bone

Leather Biker Jacket by Mango

Men's White Shirt by J. Crew

Jeans by Madewell

Sunglasses by Illesteva 

Men's Learher Watch by Fossil

Classic Bag by Brahmin

Leather Slides by Jeffery Campbell

Make sure you only pick inspirational looks that fit your personal style, never try to be someone you're not.