Dating Fashion: Menswear in the New Millennium

It’s so good to see you again, my darling pr0n pals.  I apologize for the prolonged absence; it was unexpected, and I’ve longed to get back to you.  Here’s what’s inspired me today: last night I met up with a gentleman caller of whom I’m fond, but have not seen in quite some time.

Commes Des Garcons Degrade Sport Shirt - $445, Barney's Coop

Commes Des Garcons Degrade Sport Shirt - $445, Barney's Coop

They say you’re only as young as you feel, and while that’s true, it’s been a few years since either of us saw 30.  My gentleman caller, who is a handsome fellow, showed up wearing an Old Navy Polo, cargo shorts, and casual shoes.  It’s not the worst style that your blogger’s ever seen, but not the best, either.

In my caller’s defense, he confessed that he did not know how to dress; this is an affliction from which many a young man suffers: Fashion Challenged.  In today’s post, I’m going to answer the question:  how does one dress these days when one is courting a young lady of the new millennium?


Sometimes I think fashion is so simple, I wonder how so many get it wrong.  But I recognize that the basics are shown, it can become second nature for all.  I’ve done a man’s semi-casual outfit once before, for Sunday brunch; the date outfit is not so different from the brunch outfit.

We’ve got the usual April heat wave here in DC, where it goes from 50 to nearly 90 inside of a week.  I know your dear blogger was caught off guard, and thanked her lucky stars her summer wardrobe was machine washable.  So for our first option, let’s cut our gentleman caller some slack and show him how to properly wear shorts when drinking with a lady.

Saturday Night Date - Option 1

Here are two different flat front shorts: khaki if you’re a little bit country; plaid, if you’re a little bit rock and roll.  My gentleman caller told me he shops at Old Navy, so I found these at Old Navy’s grown-up siblings: Banana Republic and J. Crew.

On top, I like to style a button down shirt, with a tee underneath; I’m a bit old-fashioned that way.

You can stay on the safe side with a solid color long sleeve – just zhoozh bit, in the words of Carson Kressley.  You don’t have to be so tucked in, and you can roll the sleeves up haphazardly; you’re learning how to dress up casual wear, and dress down work wear.

Women know the dirty little secret of fashion is that you spend time to look fantastic, so you look as if it’s taken you no time at all to look that way.

Don’t be afraid to try something a little different and show some personality.  Put a clean, well-maintained, logo t-shirt in a different color underneath the button down; humor is fine within reason.  Just make sure you are positive about your lady friend’s sense of humor.  Or try a micro-plaid or stripe with your plaid shorts.  The general rule for mixing patterns is one big, one little; one big plaid, one little plaid.


Gordon Rush Dark Brown Leather Sandals, $135.15 at Bluefly

Gordon Rush Dark Brown Leather Sandals, $135.15 at Bluefly

Few subjects in the fashion world are as controversial as the “mandal”: the man’s sandal.  Is it a do or a don’t?  In this blogger’s opinion, the problem lies not with the poor, maligned mandal, but with the feet that possess them!

Men, it’s time for your first pedicure.  Not only is it incredibly relaxing, and pleasurable, but it makes your feet look good.  Again, women’s dirty little secret is, that our tootsies don’t look this way just because of an extra X chromosome, we pay.  As should you, if your feet plan to see the light of day after March.

If I hear even one of you asking me about flip-flops, there’s no telling what I’ll do!  Flip-flops are for the beach.  When you are not on the beach you will wear a shoe.  *breathes in*  It’s okay, I’m alright, I’m not going to hurt anyone.  Yet.

Let’s move on to long pants, which can be known as “khakis”, even when not khaki colored.  Their proper name is of course “chinos”, but lots of things which are proper will get you looked at strangely.

Saturday Night - Option 2

Observant pr0n prawns (hehehe) will note that while I put a long sleeve shirt with a short, I’ve put a short sleeve shirt with a long pant.

Of course there will be situations where both of one or the other will be necessary, depending on the weather, but playing with proportion adds interest to an outfit.

Men should not fall into the trap of buying clothing that is too big; check that your shoulder seams are actually at your shoulders.  The shirt can be a bit loose or trim, depending on the particular style – try a slimmer cut shirt if you’re a trim fellow.  It won’t make you look bigger, but buying bigger will make you look smaller.

There’s nothing necessarily wrong with a casual shoe, but it depends on the shoe.  A plain sneaker or athletic type shoe does not tell your lady guest that you have put thought into your appearance.

Puma Green Leather 'Scarred Street Low' Sneaker, $111.34 at Bluefly

Puma Green Leather 'Scarred Street Low' Sneaker, $111.34 at Bluefly

A sneaker with some color and style, paired with a solid or patterned top (choose one color from the shirt for your shoes), says that you are a gentleman of some distinct joie de vivre or je ne sais quoi, and what lady would not want that?  Of course, leather is always appropriate, and a simple driving moccasin is simple, classic, and comfortable.

A simple wardrobe of easy to mix and match pieces is what everyone should strive for. When meeting a member of the other gender, one wants to make a good impression – but perhaps not too good.  One should look attractive, color coordinated, neat, and just a smidge dressed up.  Let your clothing tell your lady friend that you have been looking forward to your outing together.

In my next post, we’ll talk about ladies, and what to wear when their gentleman comes calling.

As always, it was good for me. Tell me; was it good for you?

3 responses to “Dating Fashion: Menswear in the New Millennium

  1. Economical, and good looking

  2. i agree with you about pedicures! i took nick to his first one in february and he loved it. though i dont love mandals, flip-flops at the appropriate time are okay with me.

    another suggestion for a casual shoe are the jack purcells by jcrew. great investment because they are classic and never go out of style. not to mention they look good!

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