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Dress to impress - 3 date outfits and matching Italian shoes

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It’s Saturday and you’ve got plans of the romantic variety. If you’d rather plan the evening and not your outfit, here are some ideas that will do the dressing for you, right down to the perfect pair of leather shoes.


If you’re going to the movies…

No need to overthink this one—after all, you’re about to spend at least a few hours sitting in the dark. So you might as well think comfortable and casual. Your favorite pair of broken-in (but not baggy) jeans in a dark wash will look good without trying too hard. Keep it smart by pairing the jeans with any shirt that has a collar—your favorite J. Crew button down or a short-sleeved polo won’t do ya wrong. Pair with a clean cardigan and a pair of more casual Italian shoes like the Stewart Penny Loafer. The shoes will make it look like you tried harder while the cardigan is there for when your date inevitably gets cold in the theater.


If you’re off to a trendy restaurant…

Skip the casual jeans and instead grab a great pair of tailored trousers in your favorite color. Is it a jacket kind of place? Bring along something that coordinates, but doesn’t exactly match. Mixing neutrals is an easy way to keep within dress code without looking like you’re on the way to the office. Navy and grey pretty much always look good so you can’t go wrong with those staples. Pair with a freshly laundered oxford button down—a clean shirt is better than cologne every time—and accessorize minimally. Tie the whole look together with a pair of leather cap-toe oxfords and a matching belt and you’re ready to go.


If you’re going to grab a drink at their favorite bar…

A great staple for when you’re not really sure about what you’re getting into is a pair of slim-fit black chinos. They look good on anyone and are appropriate just about anywhere. If you think it’s going to be more of a dive situation, pair with a solid, neutral tee and layer with your favorite flannel or chambray button-down. If you think the cocktails might actually be served in real glass, skip the tee and just button the chambray. Either option looks great with a pair of boots—both chukkas or Chelsea work fantastic.