What to wear on a first date - or on any date night!
What to wear for a first date
As a Personal stylist in London, helping my clients dress for a first date is always a top priority. As a recent (ish) new member to the single gals gang, I feel it is my duty as a stylist in London to share my best tips for how to dress for a first date (although this obvs doesn't limit you luckily married and in relationships gang... promise)
Dating can be phenomenal… It can also suck. I’d say that as positive as I am as a London stylist, most of my single clients and friends hate it. It is overwhelming, nerve-wracking, tends to be underwhelming, it’s a lot of effort and then ends in disappointment or a classic case of ghosting, the ‘it's me, not you’ I have even heard ‘Let's put this on ice for a bit…’ gross.
But before we even get to the first date, we have to go through the ‘What do I wear’ saga. It usually starts with staring blankly at your wardrobe, then texting your girls, and then all of a sudden your entire wardrobe is on the floor… a ‘floordrobe’ I like to call it. And you have still made no decision and now have to tidy up… lose lose situation.
All dates are different, this is down to obvs who you are going on a first date with, where you are going, the time of year, and what you are doing so it adds another level of confusion and decision-making before you even get there. So, as a London-based Stylist, let me talk you through my top dating outfit tips and each dating scenario I can think of!
My Top tip for stress-free date dressing
For you to enjoy your first date, it's crucial that what you wear makes you feel amazing and also reflects that incredible personality of yours. Not to stress you out but you want to reflect who you are by how you dress… fear not, as a Personal Stylist this is where I can help you. It takes 1/10th of a second for someone to decide on their first impression of you… so what you wear is a form of nonverbal communication to let the world know who you are.
My dating checklist before you go on a first date;
Check the weather, wind (no Marilyn moments - this is from experience lol), and temperature
Google where you are going for a vibe check
Suss out where you are in your menstrual cycle
Tip - only text one or two friends for help - the more people the more opinions and you don't need that.
Checklist when getting ready
Pick your outfit the night before based on the above checklist
Have one… or maybe 2 max drinks when getting ready - preferably the same as what you think you will drink during the date (if you want to drink)
Make sure you can’t see your bra straps or through your top (unless it is planned and works)
Make sure you are wearing matching undies OR have no VPL knickers on that ruin stunning outfits.
Make sure your straps don't fall and that you don't have to pull your skirt/dress down when you stand - all instant outfit ruiners.
Bonus checklist to help you feel more confident when getting dressed for a date
Understand which colours suit you - outfit and make up (find out how here)
Know how to dress for your body shape (read my body shape blog here)
Suss out your dating style and personality (read my style personality blog here)
Create a dating capsule wardrobe (see below)
Create a dating clothing routine (see below)
What is a dating capsule wardrobe and how to design one
A dating capsule wardrobe is a small and curated collection of pieces that all harmoniously work together, creating endless variations of looks that can be dressed up or down with no stress involved whatsoever… sounds like heaven right? But how do you create one?
What do you need in a dating capsule wardrobe?
As a London based Personal Stylist, I believe your dating wardrobe should look a little like this;
3/4 tops and blouses
1 insane jean
1 jean alternative
½ skirts eg one mini and one maxi or leather/denim shorts
½ dresses or jumpsuits again 1 mini and one maxi
2 jackets - eg leather and denim/suede/trench
1 boot
1 trainer
1 flat shoe
Belt
Necklace/earring/headband
Of course, you must tweak it to fit your colouring, body shape and style personality as well as reflect your personal taste and the items that make you feel great. For example, if you hate dresses, don't bother adding one into your dating collection, add in another skirt and top combo. You can read more on capsule wardrobe creation here
Also, your dating capsule wardrobe does not have to be separate from your day-to-day and work wardrobe - it can be picked from your existing closet. Next up is to create your dating clothing routine.
What is a dating clothing routine and how to build one?
Another huge focus I have when working with my personal styling clients on first date looks and general dating wardrobes is making what I call a ‘dating clothing routine’ Essentially we create a look for date 1 that is worn on every first date so that you know what to wear and you know it works, you know you’ll look and feel great and it’s one less thing to stress about.
Style tip; The dating outfits will be created from your dating capsule wardrobe
I would also do it for date 2 and date three. Now it’s pretty fail proof however, the only setback with this system is it depends on where you are going/what you are doing and the weather. You may want to go as far as curating 1st date looks for different types of dates… I thought I’d share options for a variety of different dates with you so that you can start to piece together your dating capsule wardrobe and dating routine.
I suggest checking out my ‘ How to put an outfit together’ blog before which you can find here and also my ‘how to style shoes’ here.
Example of a dating clothing routine;
Date 1 - Red maxi dress, gold boots and necklace and leather jacket
Date 2 - Mini skirt with long sleeve printed blouse, boots, necklace and denim jacket
Date 3 - Mini dress, boots, leather jacket and chunky necklace
Style Tip; If you aren't feeling your usual 1st date look its absolutely fine - follow a similar look but in something that feels right at the time. If nothing feels right… stick to your dating clothing routine.
My Dating makeup and hair advice plus how far can you push your look
As a clothing stylist in London I cant claim any credit for how to apply make-up or style your hair, however, my usual advice for make-up and hair is that if its a daytime or casual date, keep makeup more natural and neutral lips.
If nighttime and dark, or at a fancier location, go a bit heavier or smokier on the eyes and a brighter lip so that it can be seen.
Hairwise - follow the same advice, less styled for casual/daytime and more considered for nighttime/fancier places.
You can apply this to how far you push your outfit style wise too. It’s so hard to advise as it’s so personal and depends on the location and time of your date too.
As a general rule, if you have a dating style of the natural, boho, or urban, I suggest keeping your looks more relaxed like your style and less intense. If you are a classic, dramatic, creative or edgy - you can afford to push your looks as far as you like. If you aret sure of your style you can read my full style personality blog here.
What to wear on a coffee date
What to wear on a park walk date
What to wear for a pub drink date
What to wear on a date night at a bar
What to wear to a low key dinner date night
What to wear to a posh dinner date
What to wear on an activity date night
What to wear when speed dating or on a mingling night
What to wear on a picnic date
What to wear from your desk to date night
Now you have an action plan, focus and my blog to follow to get you creating a dating wardrobe and clothing routine to follow to get excited about your outfits, take any decision-making away and feel super confident with.
Thanks so much for taking the time to read my blog - you have no idea how much it helps me and supports my business. Id love it if you could share it with your pals too!
BIG love,
Sian
Personal Stylist, London