j Hilburn buttons

A first date is exciting! There is a little tremor of anticipation… Maybe this will be your match!?  

Let’s start with the basics

  • Wearing the proper “level of formality” in clothing says you care
  • Choosing garments that highlight the positive makes you feel confident!


Yikes – don’t Google search what to wear: 

Maybe you Google “How to Dress for a First Date” and get information like this – which literally is what I got when I did that search choosing the above phrase. 

  • Always wear a black bra and panties — even under a white tee.  (NOT) 
  • White jeans with a black blouse or sweater and your black belt are always memorable. (especially if your backside is as broad as the Canadian Shield) 
  • A slogan tee under a fitted blazer (please don’t wear slogan tees!) 
  • Leather biker jacket with a bow blouse (Dear God, NO!)

If you are reading this, I am concerned for you DIY’ers that there is not a dependable place to go for information on this subject. 

“What to wear” specifics are tough because YOU are a unique individual and the personality you wish to convey are specific to you.   There are a hundred variables in play all of which deserve  consideration. Cookie-cutter suggestions will likely be more wrong (see above) than right.


General tips 

What I can offer are 5 easy and general tips that will help you to show up with a confident smile on your face and a sexy swing in your step, which mylove, are the most attractive features you can wield.   

Detail #1 –  Start real.  You want your date to say “wow – you look better than in your pictures!” and this is best accomplished by not posting glamour or he-man, or 10/years and 30 pounds ago pictures on your online profile.  

Detail #2 – Dress up (a little).  Assuming your first date is not outdoorsy, don’t dress too casually. If in doubt, go one notch higher in formality.  Men- if you own a “casual sport coat” (see me for details) enter wearing it over a polo and jeans.  Women- wear some kind of heeled shoe or boot with dark denim and carry a good bag. 

Detail #3 – Give extra attention to your hands and your feet.  Pedicures should be considered basic maintenance for both genders.  Climate appropriate sandals are sexy for women, not for men.  Don’t forget a fresh manicure for women – Men LOVE nail color – not talons, but manicures. .   

Detail #4 – Wear a color – people remember color – and wear a color that looks well on you (curious? Book a color analysis). Do you know how many guys actually remember what their wife wore on a first date – seriously!  This is because color evokes emotional responses that the viewer is not even aware of – lets leverage that to your benefit!   

Detail #5 –  Smell good.  Olfactory triggers (scent) are the strongest we have – who knew?  So it’s worth a little effort.   If you are inexperienced with perfumes and colognes, don’t be afraid to admit to the “lady at the counter” you need help. She’ll likely be very pleased to and quite knowledgeable.  Identify about 3, then take a break – go to another store, and then circle back – if you still like it go for it!  Note: apply your scent lightly as you are getting dressed – at least an hour before your arrival.

Specific tip

Let’s do this together.  I want you to feel like a million bucks on your date, and if something as simple as what I know can help you please let me!  Check out my three Styling Tiers to see if one is right for you, or just CLICK here to get more information about working together one on one and creating a transformation!

Ann Lindsay is Suited for Love 

Making you look effortlessly confident. 

Image Consulting      —       Personal Styling

Concierge Shopping        —       J.Hilburn Menswear Stylist

I bring confidence, organization, efficiency and FUN into your life!

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