What to wear on Valentine’s Day 2012 – The Guy’s Guide

Suggestions for dressed up, casual, and in between.

Style Scenario: Valentine’s Day 2012

If you’re lucky enough to have a date on Valentine’s Day, know that they’ll be looking great… and expecting the same out of you.  Three Valentine’s Day date night scenarios follow, each with suggestions for how your outfit might want to look.  They are only suggestions.  Links to specific products can be found in the explanations for each.

Out & real nice:  Suited, but without any of that stuffy boardroom feel.

Suit Supply, L.L. Bean Signature Flannel, and Indochino

Your date isn’t your CEO.  And if they are, you might want to have a conversation with Human Resources.  She’s going to be decked out in a dress and her favorite sparkly things.  So you should put on a well tailored suit.  She wouldn’t wear that dress to work so you need to step away from the boardroom attire.  There will be plenty of men out on 2/14 in three button pinstripe suits, white shirts, and solid ties.  You want to change it up a bit.   Here’s how to do it:

  • Choose a suit with an odd pattern or texture – Think plaids, birdseye, or flannel.  Maybe even a three piece.
  • Go with a non-white shirtGingham, grids, something that’s a bit different.
  • Mix up your neckwear – Knits if she leans brighter and more flirty.  Maybe a pindot if she’s wearing a little black dress.  Something other than a solid shined up Regis tie.
  • Or, go tieless – This is where you can wear a bright white shirt and a solid suit.  Many have said only a guy like George Clooney can pull that look off.  Horse-feathers.  Why not be her George Clooney?


Out & more casual:  An interesting blazer, dark denim, and suede shoes

Joseph Abboud, Levi's, and Florsheim

No, your blazer doesn’t have to be as loud as the one above (at CladMen for $168.68 w/ FEBFAMILY).  Just leave the plain navy rumpled chino or basic wool in the closet.  Go with a rich corduroy, or a peak lapel, or a darker plaid like this new one from Banana Republic (not available online yet… check in store.)  Even a solid blazer in an unexpected lighter shade for February, or a dark moleskin with a cool pocket square will stand out in the right way.  Most guys will be in jeans and sweaters while out enjoying a gourmet pizza or the like w/ their dates.  Keep your denim dark, your out of the ordinary sportcoat razor sharp, and consider rich suede shoes like these inexpensive Florsheims.


Staying in:  A white shirt, black sweater, deep colored chinos, and black slip on boots

Calibrate trim fit, Dockers, and Cole Haan

Staying in isn’t a license to mail it in.  Maybe you’re making her dinner or you’re making dinner together.  Whatever the case, you’ll want to be able to roll up your sleeves to help with the food and/or mixing drinks.  The black on white combo is dressed up and clean.  While expensive, the Calibrate sweater fits close (try BR for on sale options.)  The honey colored chinos, which are cheap via dockers, show you’re capable of putting on something other than jeans.  For the footwear, choose loafers or pull on boots similar to the Cole Haan shown or these from Florsheim ($132 w/ LINK20).  Forget laces.  You’re already at home.  You never know when you’ll have to get your shoes off.  Quickly.

Top candy heart photo credit: [F]oxymoron