Dos and Don’ts For First Date Outfits


First impressions are everything so what you wear says a lot about you and so we’ve asked stylist Miss Vee to help us out. 

My rule is dress to be happy! If you’re happy you will feel comfortable and natural and it’ll also help your date feel comfortable – that way you are totally approachable & can just get on with conversation.

Some Dos and Don’ts

1. Do not wear massive heels!

Wear small kitten heels, pumps or stilettos – cute and sweet – closed toe or peep toe are nice – Guys like to feel tall too – let them!

2. Do not wear mini skirts – nothing too short or you risk sending the wrong message – not to say you can’t ever wear a mini on a date – just not the first one.

3. Do not show too much off – there’s a fine line between sexy and slutty – here’s a good general applied rule to fashion: accentuate only one part of your body e.g. your killer legs = wear a skirt (not too short) and balance out by covering up the torso and arms by wearing long sleeves or really nice slacks and a strappy silk blouse that shows off your arms and your décolletage. Always dress to flatter your best feature be that shoulders, back, legs or arms.

4. Please – avoid jeans on your first date. Jeans are for informal and casual events –you could get away with skinny black jeans if they have a designer feature – e.g. a wet look

5. Accessorise – Quality is key – choose your best and match shoes to bag. Take a nice bag – Clutch oversized or beaded – no bulky bags that get in the way

6. Shoes – Cute kitten heels  – or small stilettos – nothing too high or bulky or loud

7. Jacket –cinched waits or little tailored jackets are perfect

8. Jewellry – Apply the Coco Chanel Rule – Always take one thing off before you leave – we ladies can tend to go overboard so if you are in doubt show some restraint. Have fun but choose where your statement piece is, earrings, bangles/ cuffs or a necklace. I wouldn’t go OTT with rings – great for a night out with the girls, but not on your first date.

9. Always try to wear a dress or skirt and top if weather permits

Touching lightly on the topic of Make up – keep it simple – Choose between Eyes or Lips. For dinner go with a classic smokey eye, nothing too heavy, head for earthy tones. Then pop a nice tinted gloss – that way no problem with embarrassing lippy on your teeth or needing a top up.

About Miss Vee aka. Veronica Ostro

The Fine Art and fashion graduate from National Art School and former designer, visual merchandiser & stylist to international commercial fashion houses says that she specializes in building peoples personal brands by visually translating their brand into their personal & professional image.

Her service is for clients around the world in business from CEO’s, coachers; speakers & entrepreneurs that need help to enhance their image and branding.  Veronica’s true passion is to help people portray their very best image congruent with their message. She also offers her styling services to everyday people that need wardrobe cleansing, seasonal wardrobes, shop for trends, dates, events or to dress to land that promotion.

Veronica would love to help you look and feel your best so give her a call to set up a consultation now. You can reach her at 0405 368 488.

Photo Credit: Geneva Vanderzeil


Iona is a Wellness Coach specialising in relationships and dating. She works with single women to write their own love stories.