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What to wear on a First Date

March 15, 2010 By Joe | Heads up: Buying via our links may result in us getting a commission. Also, we take your privacy rights seriously. Head here to learn more.

Kenneth Cole Video Style Guide – What to Wear on a First Date

doublefacepalm

White Jeans?  And a white v-neck tee with a gigantic graphic on it?  I hate to go back to the well of Internet memes, but this is actually what I did after watching the latest Style Guide video from Kenneth Cole —>

C’mon Kenneth Cole Style department.  Remember the first video style guide?  The “what to wear for a big meeting at work” video?  That was okay… a little rough around the edges, but it still had some pretty good tips.  This newest addition isn’t moving in the right direction.  You guys are better than this.

What they got right, and what they got wrong, after the video:

The outfit as a whole looks iffy at best.  The biggest unanswered question is: is the jacket meant to be outerwear? Or a substitute for a blazer?  Because it looks like outerwear. If he’s wearing outerwear indoors, it’ll be sorta odd.  And God help him if he takes it off to then blind his date with the white jeans and white t-shirt ensemble.

Sarah, a member of our official panel of women took a look at the video and had this to say:

“If he went on a date with a girl… I’d question his sexuality.”

It does look a bit Carson Kressley-ish.  Here’s what they got right, and what they got wrong.

What they got RIGHT:

The Jacket – Four Pocket Military Jacket – $148.50

jacket
Military style in Moderation.

The date destination appears to be quite casual.  So the outerwear should follow that theme.  The Military style Jacket from Kenneth Cole avoids all of the mistakes a lot of other military-inspired clothes make.  It’s not full of excessive pockets, huge epaulets, and other stuff.  It’s nice and balanced.

What they got WRONG:

The Jeans – NO: White Denim – $69.50 | YES: 5-Pocket Darker Denim – $69.50

jeans
White jeans on the first date will cause questions.

What they got wrong was everything else.  Starting with the white jeans.  Some guys can pull off jeans, and good for them.  No guy can pull off white jeans on a first date.  Fifth or sixth date?  Okay.  Maybe.  But on that first date you don’t want to give her any more reasons to over-think.  White jeans will do that.  Stick to darker denim.  Easy on the whiskering and details.  Don’t stray too far from plain pockets and a straight fit.  And if you’re looking for something cheaper, Levi’s 501s will always work.

The Shirt – NO: V-Neck Graphic – $35.00 | YES: 1mx Fitted – $49.50 & plain tee – $7.00

shirts
Trying too hard vs. Casual Class

Y’know how they say you can never go wrong with a white oxford?  A first date is one of those times when not only are you not going wrong, you’re getting it right.  The Fitted Express 1mx is cut short enough in the tail and close enough in the sides that it can be worn un-tucked.  Layered over an agate-gray athletic cut t-shirt, and you’ve got the same color palate as the Kenneth Cole Tee.  Only you’ve subtracted all the clubby frat-boyishness.  Lightly iron the 1MX but don’t have it pressed or use starch.  And put the collar stays in.

The Shoes – NO:  Hidden Vision Sneakers – $88.00 | YES: Clarks Desert Boot – $95.00

kcshoes
Avoid looking immature. Stick with boots.

If it’s a casual date, wearing your freshly shined pair of black laceups isn’t a good idea.  But wearing a pair of shoes that makes you look like you just got back from the skate-park… probably isn’t so smart either.  You want to be casual and comfortable, but not sloppy.  Classic American Sneakers have a thinner silhouette, but desert boots are the best play.  They’re smart looking, but aren’t a dress boot.  Perfect for coffee, a walk around the zoo, or catching a movie and beers afterward.

The Watch – NO: Skeleton Watch – YES: Classic Black – $150 or DKNY Brown  – $105.80

KCWatches
Keep it simple.

There’s just too much going on with that Skeleton watch.  Plus, you’re showing off a movement that’s made in… China.  The Kenneth Cole Classic Round Chrono looks slick if you’ve decided to stick with black shoes.  But if you’ve taken the suggestion for brown desert boots, stick to a brown leather watch.  You don’t have to match your watch band to the rest of your leathers, but it’s a bit of a reach if you don’t.  Always match your shoes and belt.

The Bracelet – NO: Braided Leather Wrap Bracelet – $45.00 | YES: Nothing. – $0.00

kcbracelet
Keep it even more simple.

Are you Johnny Depp?  No?  Okay.  Don’t wear a bracelet.  Especially not on a first date.

…
You probably won’t be totally comfortable on your first date.  Hardly anyone is.  But following these wardrobe suggestions should help you maintain at least a small piece of sanity, and allow your personality to be the first thing she notices.  Not your clothes.  Although when she notices your clothes she’ll still like them.

(Your Thoughts?)

Filed Under: Accessories, Clothing, Etc., Shoes, Watches, Women Tagged With: Kenneth Cole Video Style Guide what to wear on a first date, Outfit suggestions for guys, What to wear on a First Date, White Denim

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Comments

  1. Dave P. says

    March 15, 2010 at 10:38 AM

    Wow! Worst advice ever Kenneth Cole! Gentlemen, take it from Dappered, keep it cool, and classic. You can make enough mistakes just opening you’re mouth, don’t compound it by looking like a cheesy goof!

  2. Martin S. says

    March 15, 2010 at 7:13 PM

    Unfortunately, I have to disagree with Dappered on this one. I am assuming the writers are not from NYC, no? If you notice, the problem the model is supposedly having is that his date has only seen him in his conservative work attire. Thus, the date outfit is meant to showcase a softer, less stiff side of himself. White jeans hit this on the money. Caveat being: few men exude the confidence required to not look foolish. In my opinion, NYC men tend to be a little more confident than men from other locales. Being that he is a model, he has the physique and confidence to wear them well. V-neck is the right call–however, real folks should stick with plain white or grey–no graphics! I personally agree with desert boots over those sneakers, but I understand why he chooses those. Also, desert boots are probably harder for the average pan to wear without looking crazy than are plain sneakers (i.e converses, jack’s, sambas). I personally thought this was one of KC’s better displays. However, I would have loved to see him accent it with a nice scarf, since he’s wearing sneakers. But overall a good combo, safe combo.

  3. Ryan says

    March 15, 2010 at 9:53 PM

    I’m somewhere between Dappered and Martin on this. I endorse some clothing for the very reason that it’s not the traditional look. So that’s why I would wear the white denim.

    But, and this is a big ‘but,’ if you’re going to do something more daring like that, the rest needs to fall in line. So absolutely NO graphic shirt. Dappered’s right that the bracelet is also a huge mistake.

    I can dig a pair of classic black sneakers like those in the video.

    All in all, I think this is an awful style guide from a company that I really like.

  4. Bar None says

    March 15, 2010 at 10:08 PM

    New York men exude more confidence? Or do they just have a screw loose. The secret to pulling off the V neck is to be a woman. And graphic tees are as edgy as teeing off on a par 5 with a driver. Graphic tees are totally trendy and are most often worn by high school kids. My girlfriend commented that it was my dress shirt, blazer, dark jeans, and casual brown leather shoe that got her eye. White pants are very dangerous. There are so many things that are disgusting, you bump into them with white jeans and there is no hiding it. Darker pants you can cover it up a bit. I did like the military jacket though (not a fan of the collar popped). Finally, I never take fashion advice from someone wearing a zip up sweater. Sweaters should have buttons or nothing, ask Mr. Rogers.

  5. Billfold says

    March 17, 2010 at 3:12 PM

    Hey guys. Relax. It’s all subjective and a matter of personal taste. First dates are always an effort presenting your true self and not about “playing it safe” w dark denim and a collared shirt. It’s 2010. The rules have changed. Get with it!!

  6. Steven Kippel says

    March 19, 2010 at 9:16 AM

    I literally facepalmed with that cheesy line at the end.

  7. Steven Kippel says

    March 19, 2010 at 9:26 AM

    Now, on a first date (or any date for that matter), be a gentleman. Respect her. She’s putting effort into how she looks, don’t look like a slob. This Kenneth Cole look was too much Jersey Shore. They seriously took a man who looked like a man and then made him look like a child.

    So what if she’s only seen him in business attire? She agreed to the date in that business suit. Wear a damn collar at least.

  8. Callie says

    March 22, 2010 at 3:37 PM

    Speaking as an early 20 something female, I would say the graphic tee/white jeans/bracelet combo looks like he’s trying too hard. One of those at a time would be ok. However, I do agree with most of what Dappered said. Just as long as there’s nothing too extreme in the outfit, you would look just fine.

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