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.



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.





Valentine’s Day Gift and Seduction Guide

Ok Gentlemen, it’s that time of the year again.  Although you should be showing the woman in your life how special she is every day, this is the time to really shine (no pressure!).  Fortunately for you, I have spent 13 years of my career working with lingerie brands all over the world styling their ad. campaigns and fashion shows.  I have styled the most beautiful and sexy women in the world, and had the privilege to work with photographers and directors that together have mastered the art of seduction.

Executive styling and lingerie…………..never do these worlds collide as beautifully as they do on Valentine’s Day.

I am going to assume you have already mastered the art of style and being a gentlemen, so let’s focus on the woman in your life!  If you missed this, or need to freshen up your skills, check out my previous article on “Dating and Being a Gentleman.”

Valentine’s Day should be about being together, about stepping away from the routine of everyday life to add a serious infusion of love and romance into your relationship.   Every woman dreams of romance…………her knight in shining armor so to speak.  We all want to be swept off our feet and treated like princesses.  Of course every woman is different, but the basic principals never change.  We all want to be loved, adored, admired, and feel like we are the sexiest woman alive.  We want to be courted.

The perfect Valentines Day date will depend on your woman, but honestly, it can go one of two ways.  You either plan an evening out, or you plan an evening in.  Those are your only 2 choices…………either of which involves planning.  Sorry gentleman, this is a tough holiday to leave till the last minute.  A gift alone is NOT enough!!  An evening out can be as simple or extravagant as you like, but I highly suggest planning something that calls for the two of you to dress up.  This can be dinner, a wine bar, a jazz or supper club, or perhaps a rooftop lounge.  Anything candlelit that requires a cocktail dress and heels is a safe bet.  On the other hand, an evening in requires YOU surprising her with a romantic candlelit dinner.  Make sure to set the mood via candles and music.  Ambiance gentlemen, is very important.  Nothing is sexier than watching a man cook and pay attention to all of the little details that go in to planning a romantic dinner.  To add a little spice to your evening in I highly suggest surprising her (and ultimately gifting yourself) a luxury Box of Grey flight case (which comes complete with sexy lingerie, sexy toys, massage oil candles, and anything else you can think of that would add some serious spice and romance to your evening).  You can purchase one of their curated boxes, or customize one yourself to fit your desires.  I promise…… will thank me later 😉

Now that you have chosen the date, let’s talk about the gift.

No, it’s not a given that you give her something in addition to a romantic evening, but it sure will make her feel special (and that’s the whole point, isn’t it?)  Just like the actual date, the gift can be as simple or extravagant as you wish.  The whole point is to make her feel special, so take the time to think about what it is that would make her smile.

For Valentine’s Day, there are only 4 categories of gifts that are appropriate: lingerie, jewelry, flowers, or chocolate (or a combination thereof).

Whatever you give her it has to have at least one of these elements……………trust me on this one!  Below I have selected some of my favorites.


Just in case you are one of those guys that have left buying a gift till the last minute (as in ordering online is a bit risky), or like shopping in person with a qualified salesperson on hand to help you, I highly suggest you visit either Agent Provocateur or Journelle here in NYC.  Both of these stores provide a very boutique experience, and have very friendly staff on hand to guide you through what can be quite a daunting experience for a guy.


 If you live in NYC, and are going to give jewelry, I HIGHLY suggest taking a trip downtown to Greenwich Jewelers.  Not only do that carry an amazing selection of jewelry, their customer service is outstanding.  A few of my favorite pieces have come from them, and I can’t think of another jewelry store in the city that has such a beautiful and unique collection.   It is a very small boutique style store, so you won’t feel overwhelmed like some of the large chain stores………..and you most definitely will get individual 5 star service.




If you have any questions or are in need of additional suggestions please don’t hesitate to leave a comment below or send me an e-mail at  As worded so perfectly by Box of Grey – “Make your one night outstanding.”