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

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 shirt – Gingham, 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

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

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
Why? In case you spill something on your shoes?
The tieless suit look just doesn’t work. Even for Clooney
yes, love juice.
Tieless with a suit can absolutely work. Just wrangle the collar in with some Wurkin Stiffs.
Completely agree with John. Love the tieless with a suit option. Good collar stays are a must. Don’t know why so many people are so scared of this look.
If you think this look doesn’t work then you’re forgetting the whole purpose of style. Tieless works just fine in many situations. So long as we avoid the whole shirt lapels over your jackets lapels it looks great if done correctly
I’ve never heard of anyone having an issue with tieless suits until reading this site…honestly I can’t understand why it’s even a remotely controversial style. Personally never seen it look odd or inappropriate, and if it did it would probably be because of the fit or style of the suit/shirt chosen as opposed to the fact that there was no tie.
First two looks are great. Not really feeling the last one. If you’re at home why are you wearing boots at all? I get the slip-off thing, but they have loafers for that. Bonus points if you own a pair of badass slippers. Also, if you do kick off the shoes you can show off your argyle socks–a nice contrast to the muted sweater and chinos.
Full disclosure: I think Chelsea boots are ugly, but I think the boots at home thing still stands.
Stark contrast = formality. Here we have the most formal pairing of solid white shirt and solid black/navy suit, and yet, the necktie is absent. Going tie-less is less of a statement when pairing a sports coat with a gingham shirt.
Tieless with a suit only works if one wears very casual footwear. Leave the park avenues at home.
I had my Valentine’s Day this past Saturday. We went to an expensive, but relaxed restaurant. I went with the tieless grey suit, and I was still the most dressed-up person in the place. I wore walnutty wingtips to keep it on the less formal end of the dress shoe spectrum.
I wasn’t 100% plesaed with the end result, but my wife sure was, and that’s all that really matters on Valentine’s Day.
The suede florsheims are cheaper at k&g with more sizes
I think I’ll be rockin’ a crisp white shirt, black suit, and purple fluffed handkerchief. And no tie!
Come again?
Lol you caucasian people wearing shoes inside the house. 😛 Nice picks though!
I think it should also be noted about those Docker’s pants that the Docker’s website is having free regular shipping until 11:59 pm PST tonight 2/13/2012
^ This. Yup. Nice work Alan.
Seriously, any self-respecting Asian would never have shoes on inside the house
I’ll be staying in tonight, and will wear dark jeans, a dark grey v-neck, and a red/blue/white gingham shirt (my girlfriend’s favorite shirt). No shoes, because what kind of barbarian wears shoes indoors?