I am by no means world expert on shoe eyelets, but I’ve put a lot of time into learning and researching since I decided to treat myself to a hardware press for a birthday some months ago. I also promised @thenewreligion elsewhere that I’d write up some key points to share, for him and others just starting out.
Key Points
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Shoe eyelets are not universally standardized. They might be more of a procurement challenge than you expect.
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Only buy eyelets if you can also buy tools confirmed to properly set that specific model and size. Sometimes that will be tools designed for that specific eyelet manufacturer, model, and size. Sometimes it could be tools designed for eyelets from other manufacturers that other makers or repairers have confirmed give good results with the slightly differently sized eyelets you’re buying.
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Presses are faster and can yield better, more consistent results than hand setting tools, especially on the back sides of eyelets. However, hand setting tools are often much cheaper. They also avoid the terrible issue of compatibility between tools and presses.
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If you’re just starting out, it might be cheapest and easiest to buy eyelets and setters in the common US sizes of 00 (3/16" barrel internal diameter) or 0 (1/4" barrel internal diameter). These will often be sold as “grommets” rather than eyelets, perhaps with matching washers included. You can get kits for these from hardware stores, Tandy Leather, C.S. Osborne dealers, and even Harbor Freight. However:
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These sizes are probably either narrower or wider than the eyelets you may be used to seeing on shoes and boots. Their proportions of flange and hole diameter also differ. They may just not look right to your eye, giving more of a DIY appearance.
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The barrels of these eyelets—the round tubes that go through the material—are generally made long enough to hold a couple layers of fabric together, rather than leather. They may be too short, especially if you’re using thick leather or lining. Manufacturers often give “length under flange”—the height of the barrel underneath the flange that sits on the top of the material. Keep in mind that you need some length of barrel extending beyond the thickness of your uppers on the backside to peen over with the setting tool. The thickness of material you can grip with an eyelet is less than the length under flange.
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There are relatively few actual manufacturers of shoe eyelets. They want to deal in large quantities, not small baggies of eyelets for single pairs or repair shops. So you are probably going to end up buying from a distributor who buys in bulk, splits into smaller quantities by weight rather than by piece count, marks up, and resells. Don’t forget to check your local shoe repair supply.