Dressing For A First Date

Whether it's a blind date, a set-up or you have a history with this person, it's important to acknowledge that the first date could be a start of something new. Check out our tips to help you feel and look your best on your first date!
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Call us old fashioned, but the first date is crucial and can set the tone for the potential future of the relationship. Whether it's a blind date, a set-up or you have a history with this person, it's important to acknowledge that the first date could be a start of something new. Check out our tips to help you feel and look your best on your first date!


Last summer while I was doing some work in Paris and attending a few fashion shows, I met an inspiring woman, a force in the fashion industry. We had a wonderful connection; as we were discussing our lives and careers, we discovered that our missions were the same -- to help women feel confident and empowered through style. She told me to check out a documentary called "Miss Representation" that shows how the media, controlled by men, sets the standards of what is sexy. This standard has a tendency to cause young girls and grown women to believe that if you are not hot as the standard dictates "hot," then you're not interesting or desirable. She also brought up the fact that a few of her friends and clients (some of them post 50) are finding themselves single and having to compete with younger women.

I have always believed and said two things: "Goodness is glamorous and healthy is hot" and "The party is never over, no matter what age you are." Girl power stuff is great, but you're probably being realistic and asking yourself: "Now, what party am I going to? And what the hell am I going to wear?"

Newsflash: It's not a short, stretchy dress, nor is it letting it all hang out. A client once said to me that once you're in your 50's, a game change happens and things that used to work for you don't work anymore. To feel desirable and sexy, you shouldn't look like you're trying too hard. Yes, most men are attracted to the obvious, so I'm not telling you to belt a burka and run out the door. Let's discuss where you are going before I give you tips and inspiration on what to wear. Think of your looks as flattering uniforms that are assigned for different occasions.


Isabel Toledo once said that shoes are a woman's pedestal. A shoe can make or break a look, so it's a good idea to build your looks starting with a comfortable, modern and sexy shoe. And it doesn't have to be a 5-inch stand-and-pose stiletto.

Here are some ideas for your date looks. The gorgeous model shown from our latest book "Work It!" is our fabulous friend from Chicago, Lynn McMahan. Lynn is known as the "Green Glamazon" because of her work as a "green" developer.

Daytime Date / Coffee Date / Museum Look: Wear a knit and a coat and go for a warm flattering color to create a soft tonal look. Add a pair of well-fitted jeans, a heel bootie, a bag and you're ready to go!

This look: Loro Piana coat and turtle neck, J. Brand jeans, Hermes Bag, Prada booties with rubber soles. This type of look can also be found at Banana Republic for a sweater and coat, Levi's for jeans, and Stuart Weitzman for booties.

Movie Date / Casual Dinner: Go for a comfortable dress (so that you can sit through the movie!) that shows the waist and looks sexy without trying too hard. Keep the look clean and follow the rule of one embellished piece: in this case, the accent is on the boots. Add a denim jacket or a VT Luxe Convertible Loop and a shoulder bag.


This look: Azzedine Alaia dress, Oscar de la Renta boots.
Get the look for less with this version: Calvin Klein dress, Ellen Tracy boots at Macy's, VT Luxe Convertible Loop.


Dinner Date Look: Every person has a shade of blue that looks flattering on them (for more info on how to pick your perfect palette see our book "Life in Color"), so you can't go wrong with a beautiful blue ladylike dress. Here, we paired it with metallic platform heels for a modern look. Throw on our VT Luxe Soft Flutter Wrap to stay warm.

This look: Yves Saint Laurent dress, Jimmy Choo peep toe platform heels
Get the look for less: Lauren by Ralph Lauren satin dress, Nina "Fonda" Sandal from Nordstrom, VT Luxe Soft Flutter Wrap.



Skin is in. The more natural and fresh you look, the better for a day date. Keep the palette soft and warm, and the lines clean. For a dinner date, choose to emphasize either the eyes (see Lynn's makeup) or the lip, but not both at once.


Run, don't walk to your underwear drawer and get rid of your granties and anything tired looking! It's always good to refit your bras by an expert and sex them up a little from time to time. Each one of our clients doesn't start her look without modern shapewear -- it guarantees smooth clean lines and is the finishing touch to "feelin' it" on your date! -Jesse


There are a few key factors to consider when dressing for the first date: for starters, where are you going? You want to be sure that you are appropriate for the setting.


Extremely Casual: If you are meeting for a casual coffee, I would suggest a nice sweater over a shirt and your most modern fit, darker denim jeans with a nice shoe.

Semi Casual: If you are meeting for lunch or a low-key dinner, I would suggest your best fitting jeans or casual pants and a casual blazer or jacket over a pressed shirt with a great pair of shoes.


Dinner: Always wear a jacket paired with a nice shirt or shirt with a sweater combo to dinner. Even if the restaurant is more casual, you can remove the jacket once you sit down. The jacket will show that you put forth the effort to look special.


Photo: Corneliani / Bloomingdales Catalog
If you remove your jacket, you will still look put together with the shirt and sweater combo. The pocket square is a nice touch that will make you look like you put a little extra effort into getting ready. This is perfect with jeans as well.
Photo: Paul Stuart

Your shoes should be clean and polished. Get inspired by these Alden for J. Crew cap toe boots. They will look great with jeans and a blazer.
Photo: J. Crew

Wear something that is flattering to your skin tone. If you are unsure, the blue trick we mentioned for the ladies always works -- most people look good in and respond well to different shades of blue.


Grooming is one of the most important details in preparing for your first date. Rule number one -- don't overdo it with the cologne. Fragrance is something that should only be detectable when you are in an intimate situation, it shouldn't be the first thing one notices about you. Be sure your hair is freshly cut or styled and your nails are clean and manicured. If you wear a beard, be sure it's neatly trimmed, or if you normally are clean-shaven, keep it fresh. Fresh breath is important, but chewing gum can be a turn-off. If you are picking up your date in a car, be sure it's clean and smells fresh.


Be sure that whatever you decide to wear, it represents you and your personality. Even if you are a jeans and t-shirt guy, you should step it up, but maybe go for an unstructured jacket or one that translates from outdoor to indoor paired with a really nice shirt or sweater/knit. If you are typically more of a button-up kind of guy, take it a step further, wear a pocket square or a modern necktie with a tie bar. Whatever you choose, you have to wear it and not let it wear you. You have to feel comfortable and on your game but let the extra effort empower you rather than burden you. -Joe

Now that you're inspired and putting together the best version of yourself, remember to have fun! The more comfortable and confident you feel, the better the date will go.

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