This story was originally published in January of 2013, but we brought it back again for all you guys who need some good Valentine’s Day ideas…

You’re not the average guy. She wouldn’t want to date you if you were. But thinking outside of the box for a date night to prove your above average status can be hard work. And we all know that a poorly planned date can be like standing on the sinking Titanic, except instead of hearing the orchestra play to the bitter end, it’s just the sound of silence – and no, not Simon & Garfunkel…just actual awkward silence. So to save you from the clumsy moments of checking your smartphone for the umpteenth time in hopes that Will Smith from Hitch would save you via text (he won’t), we put together a few plug-and-play date ideas (female approved) for your next night out with that sig other (or prospect).

And remember, when it comes to planning a date night, a little sprezzatura goes a long way. You want your outfit to be just like the date itself – smooth and charming so that it looks like you tried, but not overly planned out like you tried too hard. With that said, a little thought can go a long way.

Here are five date and adjacent outfit ideas that will set you apart from the rest:


date outfit idea

Date Idea #1: “Skip the French fries.”

Women love anything French (we asked around to confirm). Simply mention Paris and most women will have La Vie en Rose playing in their heads. There’s something overtly romantic and sexy about all things French. Parisian chic is way different from chic. Chanel Paris, way different than Chanel SoHo. This is your chance to make her feel sexy, make her think you’re cultured (whether you are or not) and increase your chances of amour. Start out with a nice French dinner and order something using the proper pronunciations – e.g., coq au vin is not pronounced “cock ow vin”, which sounds like the undesirable symptom of an STD. After dinner, watch some independent French flick with subtitles and end your evening with macaroons from somewhere like Ladurée. Make sure to buy her some to take home so she thinks of you and your romantically French evening the next day.

The Look: 

  1. Club Monaco Oatmeal Crew Neck
  2. J.Crew Secret Wash Button Down
  3. Bonobos Stretch Wash Chino
  4. Dolce & Gabbana Patterned Scarf
  5. Vans for J.Crew Canvas Sneakers

New York City Date Spot Tips: Le ParisienThe Paris TheaterLaduree


date outfit idea

Date Idea #2: “Top Chef”

A cooking class could be a good indicator of whether you’ll have to feign enjoyment whenever she wants to cook for you in the future. This kind of a date really scores points on both cultural and culinary levels. Women love doing something in addition to actually getting a meal. And depending on how your date is going, she’ll be thinking about the next time you two can cook something up before you’re even eating. Whether you can tell a chef’s knife from a santoku isn’t the point here. You’ll engage in a shared learning experience with an amazing meal at the end. Wear a shirt that looks better with the sleeves rolled up, something where you won’t flip out over a beet splash or wine stain…but keep the club soda nearby just in case.

The Look:

  1. Bonobos Denim Chambray Shirt
  2. J.Crew Essential Slim-Fit Chino
  3. Gap Brown Braid Belt
  4. Thomas Dean Polished Chukka Boots
  5. Mougin & Picquard Watch

New York City Date Spot Tip: The Institute of Culinary Education, La Scuola di Eataly


date outfit idea

Date Idea #3: “Don’t get wine wasted.”

Wine tasting involves words like: notes, floral, legs and finishes. You’d be wise to take advantage of those key words. It’s okay if you don’t know wine; vulnerability is an opportunity to show an ability to adapt. Just make sure to hold your own. There’s nothing more amateur than a grown man that can’t hold down his alcohol. Taste each wine offered, but know that you don’t have to drink the entire glass of each – this isn’t your college fraternity wine tour where a wine glass substitutes as a king-sized shot glass. Don’t chug, guzzle or gulp. Sip and enjoy – you might actually find a wine you both enjoy and you can bring to date #2. So keep your outfit classy and finish strong.

The Look:

  1. Black Lapel Midnight Blue Custom Blazer
  2. Black Lapel White Custom Dress Shirt
  3. Canali Denim Jeans
  4. Miansai Leather Bracelets
  5. Grenson Sharp Boots

New York City Date Spot Tip: Ardesia, June Wine Bar


date outfit idea

Date Idea #4: “No air guitar here.”

What is more quintessential New York than a jazz club? There are a couple of things to note here. You don’t want to look like you’re a part of the band and at the same time, you don’t want to look like you’re attending a poetry slam. Leave the scraggly hair at home, get a haircut and don’t wear a beret or a turtleneck. There will be no “slappin’ the bass” or air guitar either. Save that for karaoke. It will be loud, and the only chance to talk will be in between songs or sets. You’ll have to lean in close to hear each other so make sure to wear some sensible cologne.

The Look:

  1. Black Lapel Charcoal Gray Custom Suit
  2. Black Lapel Pink Micro Check Custom Dress Shirt 
  3. Black Lapel Purple Paisley Pocket Square
  4. Allen Edmonds Clifton Oxfords
  5. Timex 1600 Watch
  6. Bulgari Man Cologne

 New York City Date Spot Recommendation: Blue Note Jazz Club, Dizzy’s


date outfit idea

Date Idea #5: “S’more of what?” 

This is not so much a date as a trip, so it might be for those who are well on their way towards establishing labels. But if you’re getting there, get your outdoorsman on and take her camping. You guys should be far enough along in your relationship that you know she’s one of those down, doesn’t mind getting dirt under her nails type of girls. If you’re not, you’ll find out soon enough. Skip the air mattress and opt for a snug sleeping bag. Marshmallows, graham crackers, chocolate and of course, a good bottle of peaty scotch are all a must. This will be a chance to show a different side of your style. A chance to get out of your 9 to 9 look and something more casual, functional but still stylish.

The Look:

  1. Barbour Powell Polarquilt Jacket 
  2. Wallace & Barnes Camp Shirt 
  3. Gant Puffer Vest
  4. AG Dylan Corduroys
  5. Red Wing Shoes Iron Ranger Boots (caveat: don’t try to climb the Himalayas in these)
  6. Brixon Beanie in Rust

 New York City Date Spot Recommendation:  Harriman/Bear Mountain

These are just few or many date options you can choose from. Think of these options as more than just a unique itinerary to impress her, but a recon mission of sorts for deeper insight into a potential companion. That cooking date will tell you whether or not your future children will actually appreciate home cooking over microwaveables. That camping trip will tell you whether she’s the high-maintenance type who will either go ape-sh*t over a spider or the down-to-earth type who’s ready to go into hunter-gatherer mode with you. Regardless of what you decide to do, remember to plan your outfit with as much thought as the way you plan your date.

 Have other date ideas? Have some favorite venues? Have a can’t miss go-to first date game plan? Wild first date stories? Share them all with us in the comments!