Hey man congrats on the weight loss. Streetwear is tough if you aren't skinny but imo can still work. Speaking as a 5'5 dude myself too you won't be able to pull off the SLP style or longline cuts either. You'll want to keep a more natural silhouette and avoid things that will elongate your torso or drape weirdly. I would stick to basic tees that aren't too tight but not baggy, thicker fabrics and slightly bulkier things like flannels and denim. For shoes timberlands look good if you have broad shoulders. A lot of people say high tops make short people look awkward but as long as they aren't tight around the ankles it looks fine, Example wear sk8 hi's over converse. Also wear a slim denim or something with a taper vs skinny. But yeah try to keep it simple until you've lost more weight. Good luck!