Before you buy anything
A few things worth knowing first
Buy your protective gear before you buy your skates. The instinct is reversed — people rush to order skates and treat the pads as optional. Wrists and knees are the first casualties of learning to stop, and a $35 pad set prevents that.
Decide quad or inline before you buy anything else. Quads (4 wheels in a square) are lower to the ground, more stable laterally, and where the current revival lives — better for rinks, outdoor cruising, and artistic skating. Inlines are faster and better for long distances but harder to balance on at first. If you're not sure, start with quads.
Size your skates to your shoe size, but check each brand's sizing chart — they all differ. Riedell runs true to size. Chicago runs about half a size large. A snug fit means more control; sloppy fit means ankle wobble and slower progress.
Don't buy rental-quality skates. The cheap $30 skates at big-box stores use plastic toe stops, cheap bearings, and hollow plastic boots. They're harder to learn on, not easier. Spend at least $60 for a Chicago Deluxe or $95 for a Riedell R3 — the difference in how they skate is significant.