What to wear on a First Date

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

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

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

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

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

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

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

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

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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?)