• Date Coach Jolene

Dress to Feel Your Best

A good first impression is key to wowing your date and ensuring an invitation for a second date. What better way to do that than dressing to impress? Being confident in your outfit makes the first date jitters no big deal. Make life easier on yourself by stocking your closet with interchangeable pieces that can be your go-to first date (and future date) outfits! Whether you’re young or young at heart – we’ve got you covered.

For the Ladies—

Dress it up! Keep it classy while adding some fun. Don’t be afraid to step out of your comfort zone. When polled, the vast majority of men responded that they prefer their dates to wear a dress and heels on a first date. Play it up with a dress that will fit your figure – a wrap dress can accentuate your feminine curves, where as a sheath or a tunic dress would be better for a thicker waist.

Show a little skin and choose a “sexy” area, but just one and remember you want to leave somethings to the imagination OR leaving their date wanting more. As women age, they tend to want to coverup – this can lead to giving some women a frumpy appearance. You’re still sexy, let them see it! But If you’re showing cleavage, don’t show too much leg or vice versa.

Try tops that follow your body line and avoid anything that has a stretch to it. Anything reminiscent of masculinity is the last thing you want to wear on a date. Men also generally prefer solid colors and clean lines so try and keep away from busy prints and keep it simple!

The Little Things—

When it comes to your perfume, spray and walk through it so the scent is not too overwhelming. You want them to catch of hint of it as they lean in, not from across the table. Most importantly – wear your confidence. Positive body language is the best accessory you can put on! For a first date, make sure to put on a little make up. Doll yourself up a little – if you aren’t makeup savvy, visit the make-up counter at your local department store, they can get you first date ready in no time. Don’t overdo it on jewelry. Keep it simple and wear no more than two pieces – we suggest something loose and a little dangly.

Tips for the Youthful

If you choose to wear jeans, make sure that you pair it with a high heel to dress it up a little, show some effort and keep it classy.

Develop a skin care routine that leaves you feeling confident enough to show some skin.

Tips for the Young at Heart

If you want to cover up your arms or shoulders, we suggest tying a solid colored pashmina in a shrug style to give you a little warmth while not taking away from the lines of your dress or top.

If you’re concerned about showing aging skin, we suggest Revision Skincare’s Nectifirm for firming the appearance of the neck and décolletage.

Flat bottom or clunky shoes are definitely a passé trend. You won’t be walking a marathon (probably) so think of these shoes as “cab to curb”, i.e. you’re only wearing them long enough to walk from the car to the restaurant. So, feel free to dress your outfit up with a stylish heel or strappy sandal.


Put in the effort and pick an outfit that makes you feel good! It’s not hard to find something that makes you feel confident and look good. A woman knows when you’ve gone the extra mile to look nice. First impressions count so take some time before the date to think through what you’re wearing and make sure it is clean, pressed and ready to go.

A nice button up and a dark, slimmer cut denim is a popular choice. This can be paired with a well-cut blazer in cooler months. Stay away from baggy and oversized clothes. They can make you look heavier, shorter and sloppier. Keep it simple and stick with the solids, avoid anything too loud or the dreaded “Hawaiian” print.

Drop the trainers, sandals and scuffed up shoes – women notice! A trendy loafer or stylish boot can set a casual tone but completely tie the look together.

The Little Things–

When it comes to your cologne, spray and walk through it so the scent is not too overwhelming. You want them to catch a hint of it as they lean in, not from across the table. Most importantly – wear your confidence. Positive body language is the best accessory you can put on!


We have all the confidence in you – but know that it’s ok you ask for help to ensure you feel your best. Whether you contact us, and we set you up with a stylist or you go to your local department store and let someone style you there, the main take away is to go on dates being your best self. Create a space where dressing yourself is easy so that you can feel confident, relaxed and have fun on your date!

Jolene Beaton is a nationally renowned matchmaker and dating expert. Her expertise, passion and unique ability to truly understand singles and the complex dating scene have made her a sought-after expert in matchmaking, dating and relationships. Over the past 11 years Jolene has established herself as a leading Dating & Relationship Coach with It's Just Lunch and remains focused on one key goal – helping her clients find love.

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