What to Wear on A First Date
Where I live it’s just become Spring, the flowers are blooming, the sun is shining and people are starting to go out into the world and date again. Excitement is in the air. I wanted to write about this topic because people come into my boutique and ask me what to wear on a date.
My clients always tell me that they don’t want to look “too dressy”, but would love to feel composed and put together. As a fashion stylist I feel that it’s all about hitting that perfect mid ground where you feel like the sassy minx that you are while still being comfortable, stylish and confident. It all comes back to confidence and putting our best foot forward.
Some ladies have been in marriages for a long time. One day they find themselves on their own again, outside the known comfort of the former marriage and in a place where they have lost their confidence or personal style (slowly over time). On the one had the dating world looks big, scary and daunting having not had a ‘first date’ for twenty or so years. But then on the other hand it looks appealing and makes us feel free, hopeful and excited.
We know that you are going to have a successful date if you look good because it means that you’ll act yourself and be on your game. Witty, fun, sassy and delightful.
Dates are all about excitement, butterflies in your tummy and counting down the days till you see the person. In a way, the first date is basically like an interview.
I don’t really date because without meaning to I attract men who think it’s normal to date 3 women at the same time. I would rather wear my flannelette pyjamas, clean out the inside of my fridge right after I style you for your date and hear about how it went.
There are so many different dates! The breakfast date, the coffee date, the lunch date, a walk by the river date (followed by cheese platter and wine if you’re lucky) and dinner dates (my favourite!).
Date Outfit One - Breakfast or Brunch
Wear something simple, chic, feminine and fresh. I have opted for this stunning linen cotton maxi dress. I love the idea of throwing on a breathable, light dress for a breakfast or brunch date.
This dress shows the décolletage and covers the legs (a good aesthetic balance), feels effortlessly pretty on and highlights the better assets (the neck and a little bit of cleavage) while also hiding my breakfast food baby.
I love to order a big breakfast and a chai or tea so that last benefit is key. Plus who doesn’t love to feel pretty first thing in the morning?
Fashion Fox Tip: Feel free to show your décolletage/cleavage and then to balance it out have your legs covered. A short dress and cleavage on a first date is a lot of skin. I’m not saying don’t do it, my tip is that, it’s morning time, it’s a breakfast date so ideally we want him to be looking at your face and paying attention to what you have to say. If you’ve got it flaunt it but you might be distracting the poor man with your silky smooth legs and body.
Date Outfit Two - The Coffee Date
The coffee date is not the Fashion Fox’s favourite but some people the coffee date. So I included it.
Mama Dee always use to say, that men who ask us out for coffee are “tight asses” and that I should, “run!”.
Ultimately, it’s not about the money spent, it’s about the effort. It’s short, and generally speaking we don’t get to know the other person properly.
He doesn’t have to book anywhere in advance, or prepare anything, or put any thought into it. All I’m saying is, make sure you order a biscuit and a Danish as well (haha).
I chose this outfit because it’s for you and not for him. This outfit is quick, simple and doesn’t take much effort (just like the coffee date man). Pop on a beautiful shirt with your favourite denim shorts. I love this combo because you feel gorgeous, you float in and float out, and you can pair it with a little white sneaker and keep on going with your day. Running errands after dating that tight ass has never looked and felt better.
Date Outfit Three - Lunch Dates I’ve created two outfit looks for a lunch date. One is for a warm day and the other for a cool day. You can still dress up and look beautiful, no matter the weather.
Cool weather lunch outfit
I chose outfit one because we don't often think of to wear a jumper with a skirt.
I love dresses but it's nice when we don't have to always have to rely on the humble dress. It’s such a lovely, feminine but cosy outfit and you can’t not feel pretty when you wear it. Add a closed in ankle boot. It will make you stand tall, stay warm and feel stylish. It’s the cherry on top of the outfit.
Warm weather lunch outfit
A beautiful maxi which cinches at the waist. The maxi dress is such a winner, it has everything.
It’s breezy and beautiful, feminine and chic and this one shows the shoulders, arms and upper back.
I love wearing it while sitting at a table in the sunshine, sipping a gin and soda or champagne. If you want to order dessert at lunch, absolutely do it, eat it and get it in your mouth. You deserve it!
I love lunch dressing you for lunch dates because it’s not as formal as a dinner date. We get to look at the person more because it’s daytime, we’re awake and relaxed but switched on.
Lunch dates can be really long and go into the evening.
And if things go well you can end up having drinks.
And if things go really, really well you can end up having breakfast. Whoo whoo!
So just in case, ladies, pack your breakfast outfit from the paragraphs above.
Perhaps you could wear his work shirt as a dress like in pretty woman? I approve.
And let’s hope you get breakfast in bed so then you can just wear the doona.
Fashion Fox Top Tip: Have a little travel sized bottle of perfume in your bag. Softly spritz this on in the morning and do one little spray on his pillows. It’s cute, it’s romantic and fragrance feels beautiful to wear. And beautiful to share.
Dinner Date – A table for two please
I love dinner dates so much I could squeal.
It’s all about the excitement in your belly, the night air, how it feels to do our hair, apply a beautiful lipstick, the part where we calling our friends and talk about him and the looming date night. And of course, choosing our outfit.
I love night-time because there are fairy lights everywhere.
The waiter comes out and you share an entrée and sip a glass of wine.
For my favourite type of date I’ve selected this gorgeous Magali Pascal dress and paired it with a stunning gold Valentino heel. This is perfect for a restaurant. Take an overcoat or trench coat if it’s a cool evening. I chose this combo because it’s not fitted, except for at the top. It’s romantic because it’s flowy and swishy at the bottom (yes, I said swishy).
It’s backless with thin straps, which is glam and chic.
Simply pair with your favourite clutch to finish.
Casual Dinner Date – Movies and Ice-cream
I could just throw on a tee and jeans but I’m not going to.
What I want for you is to be comfortable, feel pretty and casual but still express your identity in way that is thoughtful and subtle.
For tis outfit you can do either black jeans or a lovely leather pants.
I wore a detailed gold belt because the gold really pops against the black and sets the outfit off. I popped on a beautiful silk shirt and my favourite handbag.
Layer a beautiful detailed bralette under the silk shirt.
It looks like (and takes the place of) a necklace.
It is really important that you wear studs and not dangly earrings with this outfit otherwise too much is going on.
Button up the shirt to just cover the end hem of the bralette and just leave the first two buttons undone so the texture of the layers sits beautifully together.
If ‘Bad Sandy’ from Grease the movie was going on a date in 2020, this is what she’d wear ladies. Ah-oh those summerrrr nights!
Walking date – Let’s Get Physical
It’s nice because this date usually happens on a Sunday afternoon.
Go for a chic Italian sneaker, it’s a dressier shoe with a netted top.
I chose these over a pair of commercial/branded sneakers because it can sometimes look like you’re just rocking up in your workout gear. There’s nothing wrong with that, and you absolutely can, but the chic sneaker can take you into the evening if the date goes well. You’ll transition seamlessly from day to night should the two of you stop for a cheese platter or wine a the wine bar after your walk.
I like the walking date because you’re out in the fresh air, there’s endorphins and there might be hand holding action.
I added a chic little cap because it depends on what time of day you’re going for the walk. It can be sunny when you leave so put a cap on because it’ll make you look cute and it’s also great to be sun smart. Opt for a gorgeous black or white cap. Something plain, simple, chic and softly branded or not at all.
The Fashion Fox Tips for Re-Entering the Dating World:
· Always be yourself
· Start how you want to finish
· Dress for you, and your personal self expression and confidence, rather than for him
· Following on from this, don’t not wear something because “he might not like it” because you’ve got to be true to you.
If you’ve left a marriage and you feel ready to date again but you’re trying to get your confidence back and haven’t been on a first date for years, try this:
· Get a gorgeous new lipstick, ask a makeup artist to match you with your perfect shade
· Treat yourself to a pre-date mani and pedi
· Book in for a luxurious wash and blow wave
· Pick up an empowering, sexy fragrance such as Opium Black
TOP TIP: If a stylist, such as myself, put your outfit together for you, try not to make the mistake of innocently telling him you were styled for the date. If he compliments your outfit say, “thank you” and move the conversation along. My clients have told me that a couple of different things can eventuate.
The guy might think you bought a whole outfit just for him and then get an ego boost while thinking that you’re desperate. Some might assume that if you hire a fashion stylist for a date that you’re high maintenance in a negative way. You don’t have to take any of these tips onboard, and please always do it your way, but this is just based off of feedback I’ve received.
The Fashion Fox Personal First Date Safety Tips:
· Remember that people are on their best behaviour on the first date
· If the man isn’t nice to you or constantly makes jokes at your expense don’t see them again
· If you’re online dating, no judgement here, just let a friend know where you’re going and where you will be an when (for safety)
· Meet someone at a busy, public location, don’t meet anywhere secluded. It’s a different world now than 20 years ago. Don’t invite him to your home and then get in his car.
· Turn on your location settings and share it with someone you trust
It’s not my intention to put you off and be negative but let’s remember the things we love about dating.
It’s all about what did he smell like when he leant over and kissed you on the cheek to say hello, what did he say, debriefing the date with our girlfriends, the butterflies, the wondering when you’ll chat on the phone next, anticipating the moment you both kiss. It’s so exciting and I genuinely believe the perfect person is out there for everyone. Meanwhile, while you look fab and soak up the romance, the Fashion Fox is cleaning the inside of her pantry, trying to grow her digital foot print, labelling the jars in her cupboards, defrosting her freezer and growing her leg hair (because she can!).
If I really like a man, I will shave my legs for him.
Thank you so much for spending this Tuesday night with me. I hope that you feel inspired for your next date or first date, confident venturing out into the dating world for the first time in years or feel like dressing up for the next date with your husband or partner.
I can’t wait to show you what I’ve put together for next week’s blog. Your support, likes, comments and feedback mean so much. Love, your friend in fashion, Nicole Aka The Fashion Fox