What To Wear On Date Night

What To Wear On Date Night
Carly Jacobs

‘Um… so I’m kind of seeing this guy and I invited him to the theatre with us on Friday night is that cool?’

This text message from my mate filled with me glee for two reasons.

1. I’m a fucking brilliant wing woman. I have one marriage, one long term relationship and several quite excellent flings under my match-making belt. Social manipulation is one of my greatest gifts so if you have any single friends who are looking for romance, send them my way.

2. I haven’t been on a date in over a decade.

Mr Smaggle and I go on ‘dates’ but there’s no mystery to them. We go out for dinner, see a movie, come home and drink tea on the couch. I never wonder if he’s going to kiss me or whether we have anything in common. I don’t get to experience that moment of realising this guy might be ‘the one’. There’s no calling my girlfriends from the restaurant bathroom or giving them minute by minute run downs of the date over brunch the next day. I know most of the time dating is awful and I’m very grateful I don’t have to play that game however I’m extremely fomo and I love to experience things so I was thrilled at the prospect of witnessing a proper date.

When the big day rolled around, the date in question didn’t disappoint. He was charming and funny. We had heaps in common. He was a total gentleman and very interesting. He loved the show we went to and made sure our wine glasses were always full.

I went home that night and told Mr Smaggle what a brilliant evening I’d had.

‘He was so nice! And he asked me heaps of questions about myself. He was also really thoughtful, like we went to the bathroom and when we got back out he’d already ordered an Uber for us all!’ 

It was a fabulous night, in fact I still talk about it regularly. In the end there was no romantic connection between him and my friend but they still hang out on occasion.

Being the planner that I am, this date got me thinking about how I would prepare for a ‘proper’ date should I ever need to go on one as an adult. Most of my ‘dates’ pre-Mr Smaggle involved begging my brother to lend me his baggy cargo shorts (arguably the coolest date outfit in 1999) and my mum dropping me off at Woden bus interchange so obviously I’d have to make a few changes to my pre-date routine. For a start, my brother doesn’t even own those cargo shorts any more and secondly I would never go on a date with anyone who wanted me to meet them at Woden bus interchange. Gross.

what to wear on date night


Crochet dress made by me – If you want to learn to crochet you can join Crochet Coach here. The pattern for this dress won’t be available for a while because I made it to my measurements and my body shape is almost impossible to scale to other sizes in design so I have to re-write the pattern but I will get it published, I promise!

Shoes by Trippen – I bought these on a whim in Berlin and they’ve turned out to be an amazing purchase. They’re weirdly comfortable, I can walk for hours in them plus I don’t own any bright orange clothing so they go with almost everything.

What To Wear On Date Night

1. Comfortable shoes 

It can be super tempting to go full glam on a date night situation and bust out your stilettos but this is almost always a mistake. The best dates usually end with a lot of walking around aimlessly, hand holding and eating gelato. Or street drinking if you’re really hardcore. High heels will thwart any chance of that happening. You can still wear cute shoes, just make sure you can walk in them. You don’t want to turn down a romantic, late night stroll with the person of your dreams because you wore stupid shoes.

2. Layers 

I honestly don’t know if this applies to everyone but I’m rarely, if ever the perfect temperature. I’m almost always too hot or too cold and if I change climates too quickly, my body freaks out. If I go from a 30 degree street to a highly air conditioned restaurant, I’ll be on the verge of hypothermia in about half an hour. Vice versa, if it’s cold outside and the restaurant is warm I’ll be a sweaty, melting mess. So not hot. The answer is always layers. Personally I love a wrap, you can pop them over your shoulders if you’re chilly or drape it over the back of your chair if it warms up. Summer weight wraps can also double as head scarves if you get into a bit of bother with your hair situation.

3. Clean and nice undies 

You don’t need to go the full Dita Von Teese situation under your clothing but cute, well fitting, clean undies are definitely the way to go. Even if you have no intention of letting your date near your lady garden, it’s always nice to be prepared. I wear hideous undies most of the time because I’m terrified of VPL so when I wear cute undies, Mr Smags always notices and appreciates it.

4. Something you feel totally hot in

Even if it’s super old and you’ve worn it 100 times, wear the thing you feel super hot in. This dress is my favourite for almost any occasion. It’s fun, it’s flattering and it’s super comfortable. Yes, I’ve worn it once a week for almost two years but who cares? Everyone has seen this dress twenty times and it certainly doesn’t make it less fabulous.

5. Your regular, every day makeup 

I used to make this mistake constantly. I’d get all gussied up and ready for a date and for some reason I’d think it was a rad idea to try out a new smoky eye technique I’d seen some lithe and youthful teenager do on YouTube. This is a bad idea. Just do what you usually do make-up wise. You know how to maintain it over the course of an evening and you won’t end up in the bathroom with mascara smeared all over your eyes or blinking like a moron because you’re not used to wearing false lashes. By all means, experiment with your make-up, it’s super fun, but do it when you’re going out with the girls so at least you can wash your damn face half way through the evening when it all turns to shit.

This outfit was worn for date night in our new hood. When I say new hood, I actually mean old hood as I’ve moved back to Brunswick which is where I lived when I first moved to Melbourne. I’ve always loved Brunny and I’m loving being back amongst all the amazing European supermarkets and cheap pubs. I’ve also found an awesome new F45 studio and it’s ENORMOUS! My last studio (which I loved) was tiny and when the classes were packed I’d have to do these controlled little burpees so I wouldn’t kick anyone in the face. I could do full on cartwheels in the place and it would be totally fine. Winner.

This is also the introduction of the new outfit wall! I’ve wanted a plain white outfit since I stared my blog ten damn years ago and now I have it! So happy right now.

What’s your favourite date night outfit? Any tips you think I missed?

P.S Also you should totally sign up for my newsletter. It’s full of cool stuff.
P.P.S Don’t forget Crochet Coach has a free trial offer period at the moment so make sure you sign up!


  1. Rebekah Jaunty 5 years ago

    That custom dress suits you beautifully. Good thing you have a white wall to set it off now!

  2. Steph 5 years ago

    I just need to say, you look super amazing in this outfit! The crochet dress is actually amazing (and I’m not generally a massive crochet fan), the shoes pop and your figure looks banging!
    Love the date story too. I feel the same way about dating. I met my now husband at 16 so I’ve never done it either!

  3. Leigh 5 years ago

    Gorgeous dress! I’m so jealous that you made it! Well done…

  4. Melimum Po 5 years ago

    Hello Carly. First time ever leaving a comment ANYWHERE, but was compelled to say that you look lovely!!!! Go me, entering cyberworld. I listen to Straight and Curly with much enjoyment and just thought I’d browse your blog today while drinking my morning coffee before heading off to school teacher land. Have a lovely day xx

  5. Missy D 5 years ago

    I’m so glad I don’t have to date in today’s world with Tinder and all these apps… seems confusing. You nailed it – second that people should wear what they feel good in, then they will look good. 🙂

  6. Vanessa Bowen 5 years ago

    Aaah, dating. I thought I was past the dating phase but when my 10-year relationship ended I got suddenly chucked back into the dating pool. And it’s been a fun, sometimes cringy, experience.

    Getting ready for the first couple of dates I went on was an scene of panic and anxiety. I would spend ages agonizing over what to wear, how to style my hair, what makeup to put on and so forth. I spent ages trying to figure out the perfect costume to make myself seem like the kind of person my date would want to be with. And then I had an epiphany: I shouldn’t be wearing a costume, I can just go as myself. I was so much more comfortable wearing my favourite items and my normal makeup than trying to do the ultra-deluxe version of myself. Plus, any person who I’m going to go on more than one date with needs to like me as I am, not the super hotted-up model.

    When in doubt, go as yourself. Trust me, it works.

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