What to Wear on Valentine’s Day

What to Wear on Valentine’s Day

The so-called most romantic day of the year is coming up soon.  You’ve got a date.  Fantastic.  This is not the day to blow it in the style department.  Here are three suggestions on what to wear depending on where you’ll be and what you’ll be doing.

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Destination: Staying in

Just because you’re spending a quiet night in on Valentine’s day doesn’t mean you can open up that bottle of wine in your pajamas.  Show her that you can look decent, even if you don’t have to.

A real simple style here.  Inspired by Daniel Craig’s James Bond from Quantum of Solace, when he visits the character Mathis at his villa in Talamone Italy.  (Click Here to see the Outfit in Action)  Black fitted cardigan (J. Crew 69.55), crisp white oxford shirt (express, $29.95) khaki chinos (Hilfiger, $39.99) and dark brown boots (Cole Haan, $83.99).  Perfect for a cool sunny day in Italy, or… a Valentine’s day at home.

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Destination: Going out

Can you wear a tie with jeans?  Absolutely.  Just make sure the denim is dark, and the blazer you’ve got on is well tailored.  Alfani Red just released this new cotton poly blazer ($89.99) in a black-heather, and it could go well with either dark denim (Gap, $54.40) or a pair of light gray chinos.  Again, a nice fitting oxford, not some blousy dress shirt, and keep the tie simple and clean (Gap $29.50).  A Wool tie is a better texture to go with denim if you’re going that route.  Don’t forget the watch, This one by Triumph proves that even Chronographs can come in subtle cases.

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Destination: Something Fancy

So you’re headed to the nicest restaurant in town.  She’s putting on a cocktail dress.  You know she’s going to look amazing and every eye in the room is going to be on her when you two walk in.  Time to step it up so you don’t look like the awkward doofus who married or is dating “up.”  Pinstripe suits can make you look like a gangster, IF the stripes are set wide apart and are too noticeable.  That’s not the case on this suit from Express ($198.00).  The stripes are fine enough, and set close enough, that they’re noticeable but won’t dominate.  You’ll want to buy the pants too ($98.00). Clean navy tie (Calvin Klein $45.00), don’t forget a white pocket square, and shined up black modern dress shoes (DKNY $99.99).  A simple watch completes it (Skagen $56.00), and maybe you’ll catch a few eyes when you walk in the restaurant too.

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BONUS!!! – Under Everything

Who knows what’ll happen that night.  So make sure you’re not wearing an old pair of tighty whiteys.  Instead, wear a pair of underwear that a woman might actually find attractive.  (Jockey – $9.99 for Three)