Fashion Most-Googled: What Should I Wear for a First Date? By Christina Shanahan Published on October 3, 2014 @ 12:01PM Pin Share Tweet Email Photo: Time Inc. Digital Studio (7) The Web puts answers to every conundrum at your fingertips, but do you really want to seek fashion and beauty counsel from whoever turns up at the top of the page? In a pioneering collaboration with Google, we quizzed the non-virtual pros for answers on the Internet’s most-searched style stumpers. We know the feeling: you're meeting your date in an hour, and you're torn between a form-fitting mini and your no-fail skinny jeans. So how do you give the impression you didn't just spend the past three hours crafting the perfect balance between effortless and jaw-droppingly sexy? It's simple: Wear what makes you feel confident and comfortable. Our hit list includes layers that adjust to changing temps, curve-hugging dark jeans, flats, and a cross-body bag to have you primed for any activity. Your top priority should be choosing shoes you can walk in. "Stilettos on a grassy lawn are going to make you look like you're mincing along the whole night," says etiquette expert Anna Post. And if you're not sure of the evening's venue? "I would always avoid light denim and distressed styles just in case you end up somewhere a bit upscale," advises Post. "Clean-cut dark jeans are appropriate for a lot of places, especially when paired with a silk blouse." Shop the look (above): Crêpe jacket, Rebecca Taylor, $475; rebeccataylor.com. Linen top, J Brand, $320; at select Neiman Marcus stores. Denim jeans, Express, $80; express.com. Leather bag, Milly, $250; millyny.com. Rose gold-toned cuff, Piperlime, $38; piperlime.com. Pavé Swarovski crystal and gold-plated earrings, Vita Fede, $315; vitafede.com. Vacchetta leather flats, Rebecca Minkoff, $195; at Rebecca Minkoff, 866-838-6991 for stores. For expert answers to more commonly googled questions, head toinstyle.com/mostgoogled.