What to Wear on Valentine’s Day. For Guys.

What to Wear on Valentine’s Day.  For Guys.

What to Wear on Valentine’s Day

Need Gift Ideas too? See our gift suggestions for starters.  From cheap to pricey, with both items and experiences up for consideration (since a lot of women would rather go DO something, than have another… something)

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, $49.90 but watch for a sale) khaki chinos (Dockers D1, $36.99) and dark brown boots (Aldo, $90.00).  Perfect for a cool sunny day in Italy, or… a Valentine’s night 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 and INC both carry great casual blazers like this one ($69.98) that should look terrific after some tailoring.  Pair that with either dark denim (Gap, $54.40) or a pair of light gray chinos.  Again, a nice fitting oxford, not some blousey dress shirt, and keep the tie simple and clean (Gap $29.50).  A Wool tie is a better texture to match with denim if you’re going that route.   Don’t forget the watch, This one by Swiss Military proves that even Chronographs can come in subtle cases, and at a fair price.

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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.”  You can’t argue with a well fitting medium to light gray suit.  Even at this time of year when everyone else is wearing Charcoal and Black.  Indochino (Ultimate Gray – $295.20) makes custom suits for bargain prices.  (Click here for a full review of the suit you see above)  Plus, they run sales often and are probably running one right now.  Clean slim navy tie (Brooks Brothers – $39.95), don’t forget a white pocket square, and shined up black trim silhouette dress shoes (Kenneth Cole – $148, but they can be had for MUCH Cheaper).  A simple watch completes it (Skagen $70.35), and maybe you’ll catch a few eyes when you walk in the restaurant too.

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BONUS!!! – Under Everything

jockeylowrise2
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)

Time is running out to order her a gift in time for Valentine’s Day.  Wait till the last minute and you’ll get nailed on express, or worse yet… overnight shipping.  Get some inspiration here.