31 Sexy Winter Date Outfit Ideas, Cold be Damned

Getting ready for a first date is nerve-wracking—no doubt about it. But it’s 2017, and first impressions are more about our brains and beliefs than what we look like, right? Well, in a perfect world, yes. But what we choose to wear on a first date actually matters a whole lot more than we’d like to admit to ourselves.

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Experts have long expressed that perceived attractiveness has much to do with looking presentable, although that doesn’t necessarily mean taking those new 5-inch stilettos out for a road test, or wearing that dress that’s a little too tight, especially if it’s a first date. Why? Dates are anxiety-filled enough and being uncomfortable in your clothes only makes it worse. Plus, won’t it suck to not be able to walk a few blocks on a nice night because your heels are too high? Instead, wear things you know look good on you but won’t hinder you from being cool, calm, and collected.

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Here, 31 date-night outfits that are casual, cool, and 100 percent comfortable.

Originally posted October 2015. Updated October 2017.