What to Wear on a First Date – Style Guide Showdown

Esquire Style Blog First Date Style Guide vs. Kenneth Cole First Date Style Guide

Even the most confident men in the world can turn into puddles of over-thinking mess when they’re getting ready for a first date.  The wrong kind of brain chemicals start firing, you overcompensate with a glass or two of scotch, and now you’re standing in front of your closet not knowing what to put on.  It’s always good to have another person’s opinion, and in this case there are two extensive guides available from a couple of top notch style experts.

The Kenneth Cole Style Guide is from a few months back.  Click here to get reacquainted with their advice, then c’mon back.

Esquire’s online Style Editor, Josh Peskowitz, just released his list of “Ten Ways to Impress a First Date With Style,” via the new Esquire style blog.  You can read those by jumping on over to Esquire.com below.  Post advice absorption, return to this page right here and you’ll find the independent Dappered take.  Plus, any and all feedback, tips, and advice from your own past is hugely welcome in the comments section below.  Let’s get crackin’.

The Official Dappered.com Take

1. Wear Nice Shoes: YES – Peskowitz nails it by leading with this one.  Plus his advice to never wear flip flops (even nice ones) is also smart.  One addition to his list of appropriate footwear.  If you’re going out at night and dark jeans are appropriate, try a pair of slim and interesting boots.  These should do nicely.
2. Wear a Jacket, Skip the Tie: NO – C’mon.  What about a sweet knit tie like this one?  As long as it’s not some boardroom ready silk tie I think it’s an acceptable risk.  But yes, the easiest thing is to go tie free.
3. Unless the destination requires a Tie: YES – Yep, check first.  And on a side note, I don’t know if going somewhere where a tie is required on a FIRST date is the best idea in the world.
4. Don’t Wear a Suit: YES – It’s a date, not a job interview.
5. Wear Clothes that Fit: YES – And you should always be doing this by the way.
6. Cut your fingernails and wash your hair: YES – And wash behind your ears and trim your nose hairs.
7. Easy on the Cologne: YES – Or… maybe not wear any at all?
8. Don’t wear anything Silly: YES – As fun as it is to reminisce about the days of Oregon Trail on the ol’ Apple IIe, it’s probably not a good idea to wear your favorite “You have died of dysentery T-shirt“
9. Put your phone on silent: YES – Better yet, turn it off and leave it in the car.  And for God sakes, if you have a new iPhone?  Don’t whip it out and show her all the features.  That’s one step above asking her if she’d like to play MAGIC cards with you.
10. Check your Fly: YES – Sage advice.

ESQUIRE vs. KENNETH COLE STYLE GUIDE WINNER

Esquire.  In a walk.  No white jeans, no modern sneakers, no Jersey Shoreish t-shirt recommendations.  Follow Esquire’s advice and you’ll do nicely.