Dappered

Affordable Men's Style

  • Don’t Miss Anything
  • Start Here
  • Essentials Shop
  • Latest Deals
  • Style Scenarios
  • Reviews

What to Wear on a First Date – Style Guide Showdown

August 2, 2010 By Joe | Heads up: Buying via our links results in us getting a commission (not always, but just about), which helps keep the lights on around here. We also take your privacy rights seriously. Head here to learn more.

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’.

Click here for the Esquire First Date Style Guide
Click here for the Esquire First Date Style Guide

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.

esquirelogoESQUIRE 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.

Filed Under: Clothing, Grooming, Shoes, Women Tagged With: askmen, Esquire, first date, how to impress a woman, Josh Peskowitz, style guide

Continue the Conversation …

Want to share your thoughts on this article? Send us a tweet, join the discussion on Facebook, or hit us up on Instagram!

Don’t Miss Anything

Subscribe via email to get articles in your inbox or add Dappered on Flipboard. You can also follow us on Twitter, Facebook, and Instagram. Or subscribe to push notifications to get alerts immediately.

New Here?

Well, welcome to Dappered. Here are what we consider the most useful posts on the site if you're looking to put a little more effort into your appearance. Just want to see our favorite menswear products? Shop our essentials here.

One Store, Five Outfits: Extra 25% off Brooks Brothers Sale Items

One Store, Five Outfits: Extra 25% off Brooks Brothers Sale Items

Weekend Steal alert. Five style scenarios (mostly) mined from the just launched extra 25% off BB clearance event.

Stock Alert: The Q Timex GMT is back in stock.

Stock Alert: The Q Timex GMT is back in stock.

Back in both the blue and red, and the black and gunmetal.

Sanders Chukkas, Timex M79 Automatic Watches Under $200, & More – The Thurs. Men’s Sales Handful

Sanders Chukkas, Timex M79 Automatic Watches Under $200, & More – The Thurs. Men’s Sales Handful

Old Navy does a ten-dollar tech polo one day sale.

Follow Dappered on Instagram »

Men’s Fashion or Affordable Style?

Men's Fashion or Affordable Style?

Fashion is temporary and expensive. Style is timeless and affordable. Dappered® helps you work the retail system so that you can be comfortable, look sharp, and save money.

Want to share a great product? Email Us.
For a fit perspective, see Joe's measurements.
Make sure to read our affiliate disclosure.

CONNECT WITH DAPPERED

Thanks! Check your inbox or spam folder to confirm your subscription.

  • Facebook
  • Instagram
  • Pinterest
  • RSS
  • Twitter

Most Popular on Dappered

  • Monday Men’s Sales Tripod – Spier Winter Clearance, Christopher Ward Price Warnings, & More
  • Sanders Chukkas, Timex M79 Automatic Watches Under $200, & More – The Thurs. Men’s Sales Handful
  • header image of green beer Style Scenario: Going Green for St. Patrick’s Day – Casual
  • One Store, Five Outfits: Extra 25% off Brooks Brothers Sale Items
  • Style Scenario: Going Green for St. Patrick’s Day – Smart Casual
  • In Review: The Timex Mod Marlin Sub-Dial Automatic

Popular Topics

  • Best dress shirts to own
  • Best looking watches under $100
  • Best men’s dress shoes under $200
  • Nike Killshot sneaker alternatives
  • How to wear a suit without a tie
  • Suitsupply store review
  • Suitsupply Blue Line review
  • J. Crew Factory Thompson suit review
  • How much does it cost to tailor a suit?
  • Dopp kit essentials
  • Brown shoes with gray pants
  • Men’s style buying guide

Copyright © 2023 Dappered.com | Dappered, LLC | Dappered® is a registered trademark of Dappered, LLC

Hat tip: Magazine Pro Theme On Genesis Framework

Dappered does not collect or sell its users personal information | Disclosures: Privacy and Affiliates, Gilt.com, FTC

WPE

We work with partners that use cookies to understand how visitors use our site. Find out more.