Find deals on boots
You might think they don't exist, but from online stores like Zappos.com to discount retailers like Designer Shoe Warehouse, you can find trendy or classic boots on a budget. If you are ordering online, it is also a good idea to measure all parts of your leg (especially if you want a tall boot that fits over the calf; some boots fit really snug and some much looser). If you can only afford one pair this season, make sure it is one that is versatile, like a classic riding boot that can be worn with pants or skirts.
Also, to make your boots last for years to come, be sure to pick styles that are not a passing fad (think pink fur, over-the-top buckles, etc.) but rather more timeless (brown or black, mid to low heel). You can also make your boots last by storing them correctly in the off-season with boot shapers and a boot box.