Its slightly counter intuitive. First edit the page you want to add the image to. Then add something like the following:
[[Image:your_image.jpg]]
... except change the name, and file extension (eg. to .png) if necessary. Then, save your edit. Next, click on the link in red that appears where the image is supposed to be. Finally, use that page to upload the image.
Hope that helps.
P.S. I'm currently working on adding fashion categories to the wiki, so someday soon (ish) you'll have a page you can add your image to which will be for all items with that look. I probably would have had it done already if the cruise I just got back from didn't require me to sell my firstborn for a connection that is slower than a 1400 baud modem
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