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What to Wear on a Date: Round Two

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

So you took our advice, put on a fresh get up and charmed her with one of our last date ideas. Now there’s a text sitting in your inbox–she wants date numero dos. And maybe that first date was so good…that it was almost too good. And now, you’re anxiously asking yourself, will the sophomore outing live up to the big debut? Or will you end up another one-hit wonder? The thought of playing it safe and going with the ol’ local dine and flick trick was an ephemeral one…because the word “settle” doesn’t exist in the vocabulary of a gentleman like yourself. Unless it’s to settle a bet with a duel. But we digress. If you’re on date #2 and stuck on ideas, here are five more that will keep things moving along:

date outfit idea

Date Idea #1: Get ya Van Gogh on. (Pottery Making / Painting Class)

We get it. It may seem a bit…feminine. But women really like pretty things and even more that, they like making pretty things. Pottery making or painting  gives them an opportunity create their own pretty thing. They may discover a hidden talent…or you may discover your hidden talent for flattery or charm. Either way, it’s an opportunity for you to be encouraging, while poking some fun at her at the same time.

So help her tie that smock and start transforming some clay, together. Tell her that your mutual creation will look nice on your kitchen table, especially by candlelight, where you’ll eat the dinner you plan on cooking her on date #3. Maybe, just maybe, you’ll even get a head start and take your pretty date home along with your pretty (or very, very ugly) Aztec-inspired bowl. Just make sure you wear something that will still look nice with some complementary splashes of clay or paint.

  1. Levi’s Barstow Denim Shirt
  2. Alternative Fit Gray Henley
  3. Acne Roc UPS Slim-Fit Washed-Denim Jeans
  4. Frank & Oak Burgundy Beanie
  5. Club Monaco Mint Chad Cord Bracelet
  6. River Island Washed Boots

date outfit idea
Date Idea #2: DUMBO (Brooklyn)

Unless it’s straight for the Hamptons in the summertime, some Manhattanites might scoff at the idea of ever leaving their beloved borough. But Brooklyn has lots to offer, especially on the weekends when Manhattan is flooded with tourists. If you’ve never been to BK, start with DUMBO (for our non-NYC readers, that’s not a theme park for flying pink elephants but rather, Down Under the Manhattan Bridge Overpass).

There, you’ll find gems like the Brooklyn Bridge Park where you can relax, sip some grown-up beverages and enjoy views of both the Brooklyn Bridge and the Manhattan Bridge. As you walk, stop by Jane’s Carousel for a ride or Powerhouse Books for some coffee table book shopping. Grab some brick-oven pizza at the renowned Grimaldi’s (tip: call ahead and get it to go to skip the lines!) or make reservations at The River Café, where you can enjoy a romantic meal and enjoy priceless views of downtown Manhattan. The open spaces and scenic views of DUMBO mean you’ll be filling the time with good conversation – there’s no better way to see if two are a good fit. Just make sure your clothes are a good fit too.

Not in New York? No sweat. Replace DUMBO with your own local hip waterfront neighborhood.

  1. AllSaints Stenburg Leather Jacket
  2. J. Crew White Secret Wash Shirt
  3. AllSaints Spectrum Scarf (with one of these knots)
  4. Burberry Brit Shoreditch Slim-Fit Jeans
  5. Mougin & Piquard Chronograph Watch
  6. ASOS Leather Work Boots

date outfit idea

Date Idea #3: Nothing says “next level romance” like throwing yourself out of a plane. (Sky Diving)

She’s either into it or she’s not. But if she’s down – Hell. Yes. And one thing is for sure, your relationship will certainly be taken up a notch post jump. Just make sure you actually have the cojones to follow through because if you bail last minute, the only thing free falling will be your manhood. Oh yeah, it would probably be wise to have the big meal planned AFTER the jump to mitigate the risk of blowing chunks mid free fall.  And unless you rock the wind-blown-out-of-control-hair look well, it might be a good idea to bring a cap for after the jump.

Most importantly, be comfortable. This is the one time where it’s probably okay to wear some athletic clothes on a date – just make sure it came out of your dryer and not out of your gym bag. And if you need to calm the nerves beforehand, bring a flask (or bottle if you need more liquid courage is needed) of Brother Jack for a pre-jump toast. Cheers to an adrenaline-filled experience.

  1. Gant Velocity Jacket
  2. ASOS Bomber with Contrast Sleeves
  3. Nike Limitless Track Pant
  4. Nike Free Run
  5. Carhartt Army Cap
  6. It’s always good to have Brother Jack on your team

date outfit idea

Date Idea #4: “Broadway. It’s not a sing-a-long.” (Broadway Show)

If imitating paratroopers isn’t your thing and you’re not ready to risk life and limb for her yet, head to Broadway…just take a pass on Spider-Man because all the acrobatics will remind you that you’re a wuss. Keep it simple and bring it back to the roots: go see The Lion King. It’s a Broadway mainstay and you know the story and music will be good. It’ll be joyful and nostalgic. And if she starts singing along to Hakuna Matata, you know the rest of the date’s going to be problem free.

And if you were thinking to yourself, Black Lapel, what’s with all the casual looks today? Well then here’s your chance: blazer, nice denim, hard-bottomed shoes and maybe a tie if you’re up for it. And if you want to be in a place where there is zero chance of you running into another New Yorker (like your ex), Times Square is right around the corner. Sit on the ruby-red Stairs of TKTS and do some people watching. Ask her which Disney movie was her favorite growing up and which princess was her home girl. Make her feel like one. Just don’t be cheesy about it – cheese should be saved for that slice of cake you share at Junior’s afterwards.

  1. Black Lapel Navy Blue Custom Blazer
  2. Black Lapel Navy Gingham Broadcloth Custom Dress Shirt
  3. Gant True Blue Jeans
  4. The Tie Bar Black Wool Knit Tie
  5. Allen Edmonds Fifth Avenue Oxfords

date outfit idea

Date Idea #5: “Harlem Shake, It Up” (Dance Class)

Girls love to dance and will appreciate a guy who’s got some rhythm and moves both in and out of class. Just look to the movies: Hitch…Dirty Dancing…Silver Linings Playbook. Take note from this list, but don’t take it to too far. Do not, we repeat, DO NOT try to reenact Patrick Swayze’s final lift. Unless you’ve been seriously working that push press during those Crossfit WODs, you run the HIGH likelihood of failing to replicate Mr. Swayze, and as a result, simultaneously making yourself look/feel weak and her look/feel fat.

There are tons of dance classes to try out. Stick to something like Argentine Tango, where you will hold her close and be the lead. Avoid the Intro to B-Boying class where your amateur attempt at a Nike kick may result in a face kick instead.

On the sartorial front, err on the side of Will Smith’s clean and classic look and less on the side of Bradley Cooper’s Eagles jersey, hoodie and trash bag.

  1. Club Monaco Navy Cashmere Cardigan
  2. Uniqlo White V-Neck
  3. J.Crew Lightweight Chino in Urban Slim Fit 
  4. Converse Jack Purcell Sneakers
  5. ASOS Washed Double Rope Bracelet

You’ve created some romantic intrigue on that first date. Now you have five more second date ideas that will allow you two to prove the hype is real. And if it doesn’t work out, don’t sweat it. Good times are always right around the corner. And now, you’ll always have a good reason to go skydiving.

Have other date ideas? Have some favorite venues? Share them all with us in the comments!

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18 thoughts on “What to Wear on a Date: Round Two”

  1. Jwill03 says:

    Where is the love for the big guys like me? We like to dress nice too.

    1. Black Lapel says:

      The love is in any of the custom items made by Black Lapel. All Black Lapel clothes are custom made to your precise measurements and shape (no matter what that size and shape are). We’ve made suits for guys pushing 400 pounds and suits for guys pushing seven feet tall. We got nothing but love for the big fellas.

  2. Mitchel says:

    I have been having trouble finding some casual jeans that fit well. It seems like people don’t wear normal rise jeans anymore but I am looking for a normal rise. My waist is about 26 inches and and my inseam is around 30 inches. I must be unusually slim because I can’t find any jeans in my size.

    1. Black Lapel says:

      Finding jeans that fit when you’re on the ends of the size spectrum (larger or smaller) but the interwebs can make finding your size much easier. Start with American Apparel and Nudie, both of whom make jeans in 26″ waist sizes.

      Of course, you’re still shopping off-the-rack, which makes getting a perfect fit difficult. The answer: customize those bad boys. Places like Denim Therapy focus on tailoring jeans and can work wonders with a pair of jeans that fit pretty well.

      We realize that this is a lot to go through to get some jeans that fit you well, but it’ll be worth it when you catch a glimpse of yourself in some flawlessly fitting clothes.

  3. Belgand says:

    Women love a man who knows how to dance and nothing makes for a better classy (and classic) date than going out for dinner and dancing. As someone who dances at least weekly (swing), however, there are a couple of key points to be made that you might have overlooked. For one thing, if possible, skip on the slim fit pants. You’re going to need room to move. The cardigan isn’t a bad option because you can easily remove it, but keep in mind that whatever you wear you’re likely to get quite hot and sweaty very easily when packed into a tiny room and everybody is moving.

    But the key, most important element here is the shoes. While simple canvas shoes like that are incredibly popular with most dancers of both sexes the difference is that they’ve generally been “chromed” that is, they have had the sole covered with chrome leather, a soft leather very similar to suede. Try wearing athletic style shoes with rubber bottoms and you could very quickly end up having a foot stick to the floor when you don’t want to and either end up falling down or seriously injuring your knee. A leather bottomed dress shoe is actually a much better choice and will let you slide more readily. For the ladies it’s also suggested that you not wear heels, especially when starting out. Stick to stylish flats or, if you must have some height, a low wedge.

    While other dances are great, allow me to express some personal bias and suggest swing (particularly Lindy Hop). Forget your late 90s stereotypes and you’ll find that it’s a great dance with a very active scene. Unlike some more formal, ballroom styles this means that you can easily find a place to dance almost any time. San Francisco, for example, has dances occuring pretty much every single night of the week.

    1. Black Lapel says:

      Thanks for the tips, Belgand. The leather soled shoe is a great alternative for the guy who’s not yet ready to go fully chromed.

      You’re clearly a man who loves his dance and knows his stuff. It can be pretty intimidating, though, to be asked to go dancing with a pro when you’ve never done it before. For guys who know their way around the dance floor already, we might recommend teaching her your favorite dances rather than taking her to a class that’s way too beginner for you or a dance hall that’s way too advanced for her. The innate intimacy of showing someone something physical ought to dial up the chemistry between you two.

      Just don’t lay it on too thick when you’re showing her the moves. If she’s already letting you get in this close, don’t blow it by trying to cop a feel in the process.

  4. Jason says:

    Hey I am a bigger guy like a athletic lineman, what are your suggestion for guys like us around the 310-320 range

    1. Black Lapel says:

      Jason, these looks should work with any build. The only notable change we would recommend is to opt for a straight fit on the pants as opposed to the slimmer fit we recommend in the looks to keep with the proportions of the look. Hope that helps!

  5. Forbes says:

    I enjoyed this very much, been in a relationship for 2 years (so I must have done something right) and I been looking for new Ideas for dates like skydiving always been on my budget list. great job, great style.

    1. Black Lapel says:

      Glad you enjoyed it! And respect on your 2 year relationship! That’s no easy feat. As for jumping out of a plane and crossing it off your bucket list, well, that’s just a Black Lapel-inspired date away. 😉

  6. Jim says:

    Hey so I love everything about this article and just wanted you to know that you’re a gentleman and a scholar.

    1. Black Lapel says:

      At Black Lapel, we are indeed all scholars and most of us are gentlemen (we have a few gentlewomen). 😉 Thanks for the compliments and right back at you brother!

  7. Jovan says:

    More straight leg jeans and chinos would be welcome. These actually look better and, in fact, slimmer. But I wear my suit trousers or anything else requiring a crease a little looser than my jeans and chinos. Otherwise they become a wrinkly, grabby mess of wool halfway through the day.

    1. Black Lapel says:

      Wise points as always, Jovan. We’ll be sure to give straight legs some love in our next outfit idea post!

  8. Jimmie Brown says:

    I like

    1. Black Lapel says:

      Glad you enjoyed it Jimmie!

  9. Stu says:

    What’s with all the slim-fit pants? I understand the value of well-tailored, but since when is slim-fit the only option for pants? What’s it supposed to do for your look?

    1. Black Lapel says:

      Stu, the slim-fit pants are simply a stylistic preference more than anything. In the end, we’re all about well-fitting, well-tailored clothing. If you prefer a well-tailored pair of straight leg pants, more power to you! Thanks for the comment though. We’ll be sure to include more variety in our pants in our future look breakdowns. 🙂

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