Trend-surfing, when carried out as an extreme sport rather than as an occasional diversion, doesn't make much sense: Not only does it reveal an underlying sartorial insecurity, it also eats up a prohibitive amount of time, coin, and closet space. Keeping this anti-trend logic in mind, one can justify splurging a little on looks that are perennially au courant. Tall, classic black boots fit that bill, so we've chosen six pairs that you'll want to wear with a skirt to work, with jeans on the weekend, and broken-in next year.
The buttery leather of J.Crew's stretch boot ($178) hugs (but doesn't strangle) the calf -- the flat heels are chic and made for walking. For a heftier, lug-soled look, try Nine West's classic kickers ($159). Tommy Hilfiger's sturdy, toggled-at-the-top riding boots ($150 at Lord & Taylor) are made to last and won't go out of style. The sleek, stack-heeled tall boot from Banana Republic ($158) gives a sophisticated lift to your fall wardrobe. And Kenneth Cole (pictured, $250) has mastered the classic equestrian look. For a sensible splurge, we'd go for DKNY's thigh-highs ($495). They can be rolled up or down -- think of them as two pairs of adorable, wear-anywhere boots for the price of one.
PLUS: This Week's Sale Picks