Sooooo it’s been a while since I’ve been on a First Date, The Boy and I have been together for almost 6 years, and we still go on dates, but the pressure to look perfect has lessened. (I mean he’s seen me first thing in the morning. Before coffee…..)

Saying that, it doesn’t matter if you’ve been together for 5 minutes, or 50 years – the person you love deserves the best side of you every now and then. Dressing up for them is just one little way to show them you still care.

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So I’ve come up with three options for you, for three different date scenarios. First date or not, the pressure to look nice, AND appropriate for the situation can be stressful so hopefully this takes some of the hard work away, and encourages you to dress up for your next date, no matter what it may be!

Movie DateSHOP THE LOOK: Witchery spliced bib front top $49.90 | Colette by Colette Hayman bib necklace $9.95 | Asos slim fit blazer $73.57 | Country Road low rise jeans $139.99 | Nude shoes from $47.98 | Colette by Colette Hayman bag $49.95

A relaxed date calls for a relaxed outfit, but you still want to add a little sass – these cool printed heels have a small heel and the print shows you’ve got a little bit of spunk (without going full print!)

A blazer (rather than a cardigan) lifts your look just that tiny bit, and will keep you warm in the movies! And the big bag lets you sneak your lolly stash into the movies hee hee!


date night

SHOP THIS LOOK. Sacha Drake convertible ‘Catelyn Dress’ $279 | Colette by Colette Hayman ‘Cage’ clutch $44.95 | Colette by Colette Hayman ‘Special Effects’ earrings $4.95 | Ko Fashion by Boston Babe ‘Crystal’ heels from $59.95

Ok so you want to look nice, but the NUMBER ONE RULE when frocking up for a date is to make sure you are still comfortable! I have it from very knowledgable sources (I polled all my single, guy friends on FB) that their number one pet hate on a date is when the girl cannot walk in her shoes.

This dress is a great fancy dinner-date option – it’s classic, yet convertible, so you can wear it in different ways, so pick the style that you feel most comfortable in. Black is always classic, although if you feel like rocking a colour – go for it – or add it with a shoe, like I have here.


Active Date

SHOP THIS LOOK.  Decjuba “cindy in capri” dress on sale. Was $109.95, now $65.95 | Blue Bungalow denim jacket $75.00 |  Portmans “Maisy tote” $49.95Witchery soft checked scarf on sale $39.90 | Rubi Shoes low rise sneaker $29.95

The Boy and I went ten-pin bowling on our second date, it was such a great, relaxed date and we got some healthy competition going too! An active date is always a great way to get to know someone, but be prepared! No heels and short dresses here!

You can still wear a frock, but practical shoes are super-important! Trainers are always a practical, yet stylish option. Throw on a scarf in case it’s an outside activity and make sure you dress has some stretch in it! And most importantly, have fun!!

So go on, plan a date night soon! And tell me what you plan to wear! I’d love to know, tell me in the comments below.

Until next time,
In Love & Style Always
Cait xoxo


Would you like more one-on-one help planning outfits for different occasions? Why not book me for a Style Coaching session? You don’t even have to be in Auckland! CLICK HERE FOR MORE INFORMATION[line]