You know what's a terrible idea? Googling "best boots for fall" and then falling down that rabbit hole for eight hours. Nordstrom has a list, Vogue has a list, Glamour and Elle and Marie Claire have lists--and do NOT, under any circumstances click on the Pinterest fall boots board. You'll require therapy, and possibly a prescription to recover.
Of course, if you need a new pair of boots the temptation is too much to bear, so here is your Fall Boots 2014 Cheat Sheet: Spend vs. Save Edition. You want sexy booties? Got 'em. You need a new pair of riding boots? They're on the list, too.
You Want: A Classic Riding Boot
A classic riding boot is likely to be a workhorse in your wardrobe, so it's a good place to splurge if you've got the resources. There are a lot of lust-worthy options from the big designers, but local designer Elaine Turner's Tavish Cognac Leather Boot ($498) is a standout. The sleek design doesn't interrupt the eye with buckles or horizontal seams, and the bamboo detail at the heel is elegant and unusual.
If that price tag takes your breath away, you're hardly out of options. Over at Zappos, the Report Jadah riding boot ($69) is amazing and includes a cool, asymmetrical zipper detail that is very on-trend. (The more hardware the better on boots and bags, it seems.)
You Want: A Sexy Bootie
More is more when you're feeling spendy, so rather than going with an expensive pair of out-there booties stick with a classic style you'll wear and wear and wear--and wear out. Stuart Weitzman Hitimes suede bootie ($525, Tootsies) is elegant in black or grey; not a statement shoe, but reliable and super sexy without details that will date it next fall.
Get virtually the same look for much less with this Steven by Steve Madden Splendr bootie ($159) which comes in black suede, or opt for the neutral-but-never-basic navy. The sole of this shoe also has a nice tread, and a manageable 3.5-inch heel.
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You Need: An Everyday Workhorse Boot
For a throw-it-on-and-work-all-day, play-all-day, whatever-you-do-all-day boot, you need something simple and transitional to get you from work to dinner, but also something comfortable that won't have you leaning casually against various walls and doorways throughout the day. The 2.5-inch heel height on the Enzo Agniolini Galtis boot ($199.99) at Zappos is great for all-day wear, and easy to pair with skirts or pants. If the thought of a tall boot makes you claustrophobic, the Stuart Weitzman Parttime boot ($395) offers a similar look in an ankle boot style.
If your boot budget isn't quite in Weitzman territory, or if you're looking for something with just a little more edge, the Whitby boot ($76.95) at Emerson Rose Boutique in the Heights is pretty adorable. In taupe, wine, or navy, the wedge heel and suede keep the look casual and young, while still leaving you with money left over for fun extras like food and rent.