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What to Wear on a Date

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!

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44 thoughts on “What to Wear on a Date”

  1. Rody says:

    Hie black lapel, I’m planning to go on a date with a lady I’m trying to impress would a vest same colour with trousers, tight fit and a light shirt do?

    1. Black Lapel says:

      Go forth, Rody. 2/3 of a three-piece suit can work just fine. Keep the shirt light so there’s some contrast in your outfit and you’re good to go.

  2. Shaun says:

    Thank you Black Lapel! I used the idea of the cooking class for a second date and it was a real success 🙂 got good comments from many people at the class and most importantly from m’lady. A good tip for those that are looking at doing the same is get shoes that are comfortable to stand in for 2hrs + and to make use of the aprons that are at there, saved me a few time 😉 Again thanks for the good tips and knowledgeable write-ups

    1. Black Lapel says:

      That’s excellent news!

      You make a good point about the aprons too. Get that image of French Maid-style aprons out of your heads, guys. A good long apron can save your stylish threads.

  3. Jack says:

    Hi Black Lapel,

    love your work, really great website.
    Quick question could a grey ‘black lapel’ blazer, black shirt, black trousers and a dark purple tie go together? As i would like to wear this combination to prom.

    Thanks again, i will be sure to tell my friends about this website.

    1. Black Lapel says:

      Ah prom…it’s a big event. One of Black Lapel’s founders even, years later, married his prom date! Suffice it to say, we want you looking your best on prom night. With that in mind, we recommend editing your outfit slightly.

      The black trousers and gray blazer will work. Our issue is with the black shirt. Black shirts just never come off well with ties because the tie is either lighter than the shirt and you get the gangster costume look or the tie is black and you get the Regis Philbin circa 1997 look. We suggest going with a simple white shirt instead. You could keep the purple tie for a bit of color, or go even more straightforward with a black tie.

      One more note…keep the shoes black (and well shined).

  4. James says:

    just wondering if it’s acceptable to wear a white collared contrast shirt sans tie? I’ve always thought that ties were somewhat of a necessity with a contrast collar, but recently I’ve been told otherwise. Is this true?

    1. Black Lapel says:

      The contrast collar is a nod to the old days when shirts had detachable collars and cuffs for easier washing. The guys who used to wear separate collars wouldn’t have been caught dead without a tie on, so when we’re going for that old-school look, we always complete the look with a tie.

      That said, modern men are rethinking the contrasting collar shirt and making it work without a tie. If you’re doing that try a patterned shirt (stripes or even gingham) with cuffs that match the shirt but a white collar. Pair it with some jeans and a blazer to make the whole look a little more easy-going and you’re good to go tie-less.

  5. Designer Menswear says:

    Love the Thomas Dean Chukka Boots and the Clifton Oxfords- I think footwear is important, it really can finish off an outfit as well as accessories e.g. a watch etc. The little details do count! (Btw love the camping look you guys have put together, never seen such a brilliant look!) ~ Aaron

    1. Black Lapel says:

      Glad you like the looks. We hope you find them useful for your own date nights.

      You’re right about the footwear, all of the above are plenty useful outside of date night too. The Oxfords, for instance, will serve you all week at work and you can still kick it on the weekend in them with a pair of jeans.

  6. Black Lapel says:

    A trip to the San Francisco Bay Area is a bit of a hike from South Africa.

    No worries, though. There are some good options in your part of the world. We’ve heard about (and tasted) some great Sauvignon Blancs from Cederberg north of Cape Town.

    We’re less familiar with the jazz scene outside of the U.S. That’s why we would consult the South Africa section of Jazz Clubs Worldwide if we were going to be down your way anytime soon. They offer an impressive list of joints that swing all around SA.

  7. Brian says:

    I like that idea; only problem is that I live all the way out in South Africa but I’m pretty sure I can work something out. Thanks for the suggestion though, and the great content that you guys always produce.

  8. brian says:

    Hey guys, I really loved the Jazz club and wine tasting themes; really amazing!

    1. Black Lapel says:

      You could always combine these favorites, Brian and take your date for a day in Napa Valley and an evening at Yoshi’s in either Oakland or SF.

  9. Zack says:

    Not sure if this is in your realm of forte, but do you guys have any suggestions on functional yet stylish outfits for hiking (for example at Machu Picchu)? Particularly I’m interested in any suggestions on functional hiking boots that may even be paired with a suit later on in the day. Thought I hit gold when I saw the camping outfit but then I realized the iron rangers and cotton shirt may not be the best for braving humid conditions on rugged&muddy terrain.

    I’d love to be able to just throw on a tan blazer, chinos, and a nice pair of boots but the logical side of me says I’ll be regretting it.

    1. Black Lapel says:

      Serious hiking (i.e. climbing around the Andes visiting ancient relics) requires a serious hiking shoe. If this Machu Picchu trip is just one of many hikes you plan to take, a pair of Merrell Wilderness Originals will set you back as much as a good pair of dress shoes, but, like a good pair of dress shoes, are worth it. They can be resoled so they can be worn for years to come and they look pretty good too. That said, they’re still not anything we would wear with a suit or even a blazer and chinos unless the weather demanded it.

      The only guy who we’ve ever known to ramble around mountaintop archeological sites during the day and go out in a suit that night was Indiana Jones when he hit Club Obi-Wan in The Temple of Doom. Jones may have been a rough & tumble guy, but he was also a college professor and smart enough to know to pack a pair of suitable shoes for clubbing while traveling just in case. Hence, you never saw him sporting some dusty kicks with his tux. Take a cue from Indy, Zack, and pack a pair of loafers with your suit.

  10. Sunny says:

    Can you post a link to the specific Miansai bracelet in the photo? Thanks!

    1. Black Lapel says:

      Sorry, Sunny. This bracelet was available when we first published this in January of 2013 but it is not available anymore. That said, the Beacon bracelet is a good alternative choice and still available on the Miansai site.

  11. Albert says:

    Did you realize that almost everything in this article is french? 🙂
    I mean… Romance, cooking, wine are obviously french and Jazz is clearly from the Nouvelle-Orléans (I don’t know if it is related to its french origins, tho…).
    Camping remains, but brrrrr, worst kind of date ever :p

    1. Black Lapel says:

      You caught us Albert! Romance, cooking, wine…oui, Monsieur. Believe it or not, the original list of ideas was even more French. We edited out such obviously francocentric date ideas as: taking a Spanish class together (I mean come on, Spanish is such a ripoff of French, right?), visiting Yellowstone National Park (Who does that? French people! That’s who!), and taking her to see the latest installment in the Transformers movie franchise (Seriously, is there any filmmaker more influenced by French New Wave cinema than Michael Bay?).

      All jokes aside, Albert, you do have a point. We Americans could all take a page out of the French gent’s book when it comes to stepping up our dating games.

  12. Jcm says:

    I Like these styles. Good job and good selection 😉

    1. Black Lapel says:

      Thanks JCM! Glad you enjoyed these. Which one’s your favorite?

      1. Jcm says:

        My favorite style is the jazz club but i like the camping style too.

  13. paul says:

    Who dresses up like that to go camping…clearly someone who does not go often. /rolls eyes

    1. Black Lapel says:

      Paul, thanks for the feedback!

      1) You called it – we don’t go camping often! 😛
      2) But when we do go camping, its perfectly acceptable for us to look more stylish than 99% of other campers.
      3) Variety is the spice of life, and we’re trying to recommend pieces you can wear during camping but get use out of outside of the woods too. All the more important with the limited closet space that city slickers like us have to work with! 🙂
      4) That being said, we’ll be the first to acknowledge there is likely a tradeoff when it come to form vs. function. The camping noobs on Team BL would love some recommendations on more functional pieces from you!


  14. Terrence says:

    Interesting; while I always appreciate fashion and being classy. I don’t feel any of these looks are “ethnic friendly”.
    With the exception of the Jazz Club , which is universally acceptable.

    Man bracelets and chinos…
    canvas boat shoes and a scarf…
    I’m not exactly seeing an “urban” appeal for a date, most people these days are an amalgamation of styles and influences.
    It all comes across as more “New Englander” or even “WASPish”

    Then again, as they say; its all in how you wear it.

    1. Black Lapel says:

      Hi Terrence, Thanks for your thoughtful feedback. We were not necessarily going for “ethnic friendly” with these outfits, but rather “context friendly” to each date setting. And keep mind these outfits represent just one possibility of many for each date spot. We always encourage our readers to take what you like, discard what you don’t, and ultimately create an outfit that are uniquely theirs. Or as you so aptly put, “it’s all in how you wear it.” 😉

  15. Joseph says:

    I love the articles! If you’re ever looking to expand your material to college campuses to get younger folks into it; I’m an undergraduate student at Duke University and I’m your guy! 😉 But seriously (not that I wasn’t serious), great article!

    1. Black Lapel says:

      Thanks Joseph, glad you liked it man! Let us know what you have in mind in terms of collegiate material expansion! 🙂

  16. Marco says:

    You should do another article, like the one on Bond 007

    1. Black Lapel says:

      Challenge accepted Marco! Point us in the right direction – what would you like to see?

  17. Jovan says:

    Oh, and for trim chinos I heartily recommend Jack Donnelly Slim Fit. They’re just a tad slim in the seat for me, but for most guys without too much junk in the trunk they’ll be fine. They’re well proportioned, just slim enough and with a decent rise that isn’t too low or high for most guys. Again, can’t beat made in USA for under $100. I have a link for $20 off the first purchase on my blog’s review of them which makes them an even better value.

    1. Black Lapel says:

      Thanks for the smart recommendations Jovan. Ratio Clothing is a great company that works on a more approximate fit based on off the rack sizing. Definitely a time saver for the guys not aiming for a flawless fit. Good job on the Jack Donnelly review!

      1. Nick says:

        Leave it to Black Lapel to respond to a positive review of their direct competitor in a positive way.

        1. Matt says:

          I definitely noticed that too. Complimenting a competitor while also differentiating themselves. Classy.

  18. Jovan says:

    Good ideas. If you want another good suggestion for oxford cloth button-down and chambray shirts: Ratio Clothing. They’re less than $100, made in USA, made to order for your chest, neck, sleeves, height, and preferred fit. Beware though — the Slim Fit is VERY slim, so I’d encourage going with the Classic Fit at first (which is still trim fitting).

    1. Black Lapel says:

      Apparently Kesean Kenton has good taste. 😉

  19. Ed Choi says:

    What about THE HUSBAND LOOK? We too go on dates. Even if it’s with the same girl over and over and over(did I say over?) again…

    Where’s the love Black Lapel! You can call it Date Idea #6: “Leave the kids home”

    1. Black Lapel says:

      LOL, duly noted Ed! We will have something for the married fellas in a future edition! Speaking of which, where do YOU take the missus?? 😛

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