Wall Street Stylist Guide to Dating & Being a Gentleman

Let’s start with dressing like a gentleman, and the assumption that if you dress like a gentleman, you ARE a gentleman.

OK, now that that has been established, let’s move on to exactly what it means to “dress like a gentleman.”  I know, this is a VERY general statement…………..I will elaborate.

1. Tailoring is SUPER important!

Make sure everything is fitted and tailored appropriately.  This means taking note of your hem length, your sleeve length, and certainly no large or boxy shirts or jackets.  Think modern, clean lines.  Your clothes should skim your body, and show off your best assets.   I HIGHLY recommend you invest in at least one custom suit and shirt.  This will not cost you any more money than off the rack, but will make you look and feel like a million bucks!

 

2. Details are equally as important!

Jacket linings, working button holes on jacket sleeves, pocket squares, accessories, contrasting dress socks, layering appropriately………..these things are all really important.

 

3. NO GYM SNEAKERS!!!

If you must wear sneakers wear them because they are fashionable, NOT because they are comfortable or the closest pair of shoes you have to the door.

 

4. Get inspired!

Choose a theme or style icon to gain inspiration.  This can be a person (or a combination of people), an era, a movie, or even a location.  Having a theme will help you to remain focus and put together a “style guide” so to speak.  I do this for myself, as well as for all of my clients, and it helps tremendously.

 

 

 Now that you know how to dress like a gentleman, let’s get to the good stuff…………..what it means to be a gentleman on a date.

Recently I have have found myself having the same conversation over and over again with various clients.  Obviously dressing like a gentleman is a huge first step, but when it comes to dating that’s just what it is………a first step.  Now it’s time to step up to the plate so to speak.

Through speaking to my clients and male friends, I have discovered that most men really want to know what to do, and what will set them apart from the crowd, but are just clueless as to where to even start.  Wanting to be a gentleman really has to come from a genuine place……this is not something that you can fake (trust me, women can tell if it is contrived, or you are just doing it so she will sleep with you).  This is character, and something that will stay with you forever.

As a woman, I have been on several dates, and have experienced the whole spectrum of male behaviors (unfortunately).  I can say with a lot of clarity what the qualities are that I look for in a man, and what sets a true gentleman apart from the crowd.  This is definitely something that sets the men apart from the boys so to speak.

Let’s start from the beginning………..before you even ask a woman on a date.  Most men these days don’t have the courage to actually ask a woman out, so they do it in a very casual, backhanded way by sending a text msg or asking if they would like to “hang out sometime.”  I don’t want to be asked to “hang out.”  If you would like to take a woman on a date, then ASK HER ON A DATE!!!  A man that is forward, confident, and knows what he wants is incredibly sexy, and she will have so much more respect for you if you have the courage to ask her on a formal date.  She will feel like a lady………and yes, this is part of being a gentleman………..treating your woman like a lady.

Now, let’s assume she says yes.  As a gentleman, it is YOUR job to PLAN A DATE.  Don’t be generic.  Take into account who she is, what would make her smile.   Perhaps this means taking her to a really well designed restaurant or lounge, or to see live music (my favorite dates are at supper clubs where we get to have dinner then listen to live jazz), or perhaps to a museum or special event that is happening in your city.  Every woman is different, and it is your job to plan accordingly.

MANNERS ARE EVERYTHING!!! This should go without saying, but sometimes it is the little things that mean the most to a woman.  Open doors (and let her go through first!), pull out her chair at dinner (and let her choose which seat she wants), be polite and show respect to the waitstaff, make eye contact, and pick up the tab.  At the end of the date make sure she gets home safely.  Either put her into a cab, drive her home, or at the VERY LEAST, call her an hour later to make sure she got home safely and wish her a good night.   To me, this seems so obvious, but by the amount of men that don’t do these things, it clearly is not.  It is amazing the amount of men that take me on a date, do NONE of these things, then call me 2-3 days later telling me that they had an amazing time and they would love to see me again…………seriously?!!!  Ummm, no Sir, you will NOT be getting a second date.

 

 

 

 

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