Best Bet: Ruffle Up

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Photo: Courtesy of Fred Flare

Fall in New York is a tough season to dress for — it's too cool at night to sport just a blazer, but still too warm to lug around a winter coat. This wool-blend navy jacket is military-inspired, with decorative buttons dotting the front and ruffles that lend a feminine edge. A buckle in the back allows you to cinch the fit according to what you’re wearing, whether a silky tank or a chunky sweater. And the price isn't wallet-breaking, so, unlike your season-spanning peacoat or leather jacket, you can wear this out on chilly nights without worrying about it getting tossed around at the bar.

Hamptons Jacket, $86 at FredFlare.com.