So you’re getting ready to go on a first date? That’s awesome and exciting! It’s always great to meet new people and even spark a life-long love.
But mushy romance aside, we need to talk about the clothes. While what’s on the inside is the first and foremost important factor when it comes to dating and relationships, there’s no denying that the exterior is important too…if only for your own comfort.
The clothes you choose to wear on a first date can communicate your style, your creativity, and give a little sense of you as a person. Regardless of anyone else’s opinion, your outfit choices should be comfortable, and make you feel like you.
Welcome to our guide for what to wear on a first date, the ladies’ edition!
Note: as COVID-19 has many of us tucked away in isolation, dating is off the cards. These tips are, of course, meant for when the sun shines again and we can go out and make connections in person. Stay safe!
First and foremost, what makes you comfortable?
Feeling physically comfortable in your clothes is the first step to feeling emotionally comfortable and free to be yourself. Sure, those tight jeans may look incredible, but are they cutting off your circulation and making you want to decline those beers and snacks for fear of bloating?
If you look in the mirror before going out and you see someone you don’t recognize, get changed.
The restaurant dinner and movie date
The “dinner and a movie” date, a classic! Make sure you find out where they’re taking you for dinner, or at least get a sense of the dress code. This prevents you from turning up to a food truck in a spangled dress and heels, or a swanky eatery in ripped jeans.
“Jeans and a cute top”
Ah, the ‘jeans and a cute top’ combo, a timeless classic with many variations.
High-waisted, wide-leg jeans are ultra-chic and reminiscent of the 70s while elongating the legs. Wear with a cowl-neck tank tucked into the jeans or a cropped long-sleeved tee. Finish the look with heeled leather boots, a crossbody bag, and gold hoop earrings.
If you’re a skinny-jean gal, pair them with a silk off-the-shoulder top tucked into the front of the jeans (the ‘French tuck’). Wear with pumps or strappy heels, and a studded leather belt for texture.
Wrap knit dress and heeled boots
Wrap dresses are comfy, flattering, and are a perfect midway point between a knit sweater and a fitted dress. Something like this stunning cream wrap dress with tights and heeled knee-high boots and a slouchy jacket (for winter dates) would be stunning.
For summer dates, pick a lighter, shorter wrap dress like this with ankle boots and a denim jacket or blazer (depending on the restaurant).
Skirt, tee, and flats
A simple skirt and tee combo translates to practically any occasion, depending on fabric choice, cut, and shoe choice. For a low-key dinner and movie date, a high-waisted knit skirt, tee, and flats is an understated, cool aesthetic.
For example, picture this for an outfit idea: this ribbed skirt paired with this tee, a cropped biker jacket like this and some clean white chucks or leather loafers. Accessorize with gold hoops and a gold chain necklace, your go-to leather bag and you’re done. If the dinner is a little more fancy-than-food-truck, swap the flats for heels or heeled boots.
The fancy cocktail date
Let’s say you’re finally going on that date with a friend or colleague you’ve known for years and the flame has been growing. They’re pulling out all the stops and taking you to a super high-end bar in the city to start this new chapter off right. Great! Perfect chance to get dressed up.
Midi or mini dress with a blazer and heels:
If you’re a dress and heels type of girl, perfect. Think of light-catching evening fabrics such as silk, satin, velvet, and bead or sequin embellishments. Style it up even more with a satin-lapel blazer and strappy heels.
Or, a long-sleeved mini dress with embellishment such as this ultra-spangled wrap worn with high-heeled ankle booties. It’s equal parts rockstar, vegas glam, and party-ready.
Jumpsuit and pumps or strappy sandals:
A well-fitted jumpsuit can’t be beaten, it’s a harmonious meeting between a going-out dress and a pantsuit. A wide-leg jumpsuit with a detailed top such as this strapless number worn with simple pumps, heeled mules, or strappy sandals would be picture perfect (and comfy). Wear with a cropped leather jacket for warmth to and from the bar.
Pantsuit with silky tank:
A woman wearing a pantsuit is one of the sexiest looks ever. Imagine a pair of slim-line trousers and satin-lapel blazer worn open with a cowl-neck silk tank underneath. For example, let’s turn to trusty Zara once more and look at this bold-toned suit with tapered trousers and a Low-V blazer. You could wear it with a cropped lace bralette underneath, or a low-cut satin tank with the blazer worn open. Polish it off with simple heels and a clutch. Date or no date, that’s an achingly cool look.
The active date
Going for a long walk in a city park, or a stroll down the beach is a great way to get to know someone without sitting in front of each other, trying to fill every silence. Plus, it means you can wear your comfy activewear (aka the next step up from pyjamas).
Full-length gym leggings, tank, cropped hoodie, sneakers, and sunglasses
The perfect walking outfit, with enough layers to remain comfy should it get cold or turn out to be a warm day. Maintain your style flair by picking bright colours, or accessorizing with sunglasses, jewellery, and your go-to daywear makeup.
Tip: avoid cotton leggings (the type designed to wear under dresses and skirts) and stick to gym leggings with robust fabric and a fashion-activewear aesthetic. For example, these high-waisted leggings are ultra-comfy, offer substantial coverage, and are stylish while still being firmly in the activewear camp.
Joggers, bodysuit, and trainers
Joggers or slim-fit track pants such as these are the perfect combination of slouchy track pants and tights. Wear over a bodysuit such as this t-shirt style bodysuit as it will prevent the top from bunching, riding, or requiring constant adjustment as you walk.
The daytime coffee date
This is the type of date that fits in during a busy weekend day or even during the workweek. It’s the kind that you go to on the way to or from another commitment whether it’s work, a gym class, or going out with friends. This means you can simply wear what you’re wearing that day.
Outfit ideas for the casual coffee date:
- Ripped blue skinny or straight-leg jeans with a linen shirt rolled at the sleeves and half-tucked into the jeans. A pair of tan ankle boots, layered necklaces, and a crossbody bag (a perfect weekend date outfit that could easily take you to dinner afterwards)
- Tights, heeled ankle boots, a high-waisted wrap mini skirt, and an oversized tee tucked into the skirt band (this is a great work-to-date outfit)
- Linen playsuit or overalls with a grey marle crew neck tee or long-sleeved top underneath, and chucks or trainers (super-casual weekend outfit)
Hair and makeup
Ladies, there’s a stereotype out there that men only like “natural” beauty and are put off by heavy (or their idea of heavy) makeup. Don’t pay heed to this. If you love wearing makeup, even heavy makeup, in your “real life”, then wear it on your date. And if he judges you based on your makeup? See ya later, buddy.
By the same token, if you don’t wear makeup, don’t start now unless you want to. The most beautiful and attractive version of you is the version that makes you feel most like your authentic self. That may involve nothing but a slick of mascara and a clear balm. Or, it might be a full face complete with highlighter and a smokey eye.
The exception to this rule concerns the matter of lipstick. Let’s say he’s a great friend and you two have finally come to your senses and have taken the next step out of the friend zone. You’re anticipating an end-of-date kiss at the door. Opaque red lipstick probably isn’t going to work for this, unless you want him walking away looking like a clown. Go with a moisturizing balm, sheer lipstick, or non-sticky gloss. Hey, there’s nothing wrong with a strategic lipstick choice to facilitate a magical first kiss.
Top tip: do your hair and makeup as though you’re going out for a fun drink or night out with your best friends. You don’t dress up to impress them or try to influence their opinion of you, do you? No, you dress up to have fun and be yourself, knowing your friends don’t judge you but love you for you (the true you).
If you’re not really a makeup wearer but you want to get into it for dates, work, and social life, here’s a great look to start with:
- Tinted moisturizer or sheer foundation
- A little concealer under the eyes and over any redness
- A long-wear cream eyeshadow in a satin-finish taupe, bronze, or bone shade to match your skin tone
- Plenty of mascara
- A dust of peachy-pink blush over the apples of the cheeks
- A little bronzer just under the cheekbones and along the lower lash line for warmth
- A sheer lipstick or balm
What not to do
- Don’t dress according to what you suspect he or she would like. They’re there to date you, and your style is a part of that
- Don’t wear something that looks great but is uncomfortable as you’ll be tugging, pulling, and wriggling all night. The comfier the clothes, the more you can focus on getting to know your date.
Good luck! We hope the date goes awesomely.