If you have any friends who routinely dress well, ask them to take you shopping. In my experience, they really enjoy it (that's why they dress well themselves)

If you have any friends who routinely dress well, ask them to take you shopping. In my experience, they really enjoy it (that's why they dress well themselves), and would appreciate the challenge of helping you to look and feel your best. Another approach is to go to a store that sells the kinds of attire you'd generally be comfortable in (i.e., the kind of store that sells attire for people like you, and ask a shop attendant to dress you. Obviously there's a risk there that they'll just try and sell you overpriced stuff that doesn't suit you, so you have to be confident enough in your own judgement about what you'll feel good in, and be assertive enough to not let yourself spend more than you're comfortable with. You could also just try browsing fashion sites online to find outfits that you like. But don't feel like you need to get fancy and complicated (and expensive). Just go for simple outfits made of good fabric and that fit your body shape well.