What to wear on a first date (and why these outfits will help get you a second one)

Stuck on what to wear on a first date? These tried and tested looks will work like a charm

What to wear on a first date: holding hands
(Image credit: Getty)

What to wear on a first date can be a sartorial nightmare for single people.

As a single woman who also happens to be a fashion editor, I’ve had plenty of practice in dating and style and, after some hits and misses, I’ve finally managed to master what to wear on a first date. So if you’re about to embark on a first date and are having a wardrobe meltdown, I’ve got a few tips and tricks to help you nail that first date look.

Whether it’s your best jeans or the best dresses, whatever you decide to wear on a first date, there’s one key thing I’ve learned - be comfortable. If you’re comfortable in what you’re wearing, you’ll be more relaxed and confident, which is the winning formula for feeling your best self on a first date. 

From clingy tops to shoes that rub, avoid anything ill-fitting otherwise, you’ll be spending the whole date dashing to the restroom to re-adjust yourself, which in turn, could raise a few eyebrows.

What to wear on a casual first date

Of course, what to wear on a first date also depends on where you are going. Daytime dates tend to be more casual than evening dates, so jeans and a nice top is a fail-safe option. It's a good idea to wear flat shoes too, just in case there are any impromptu romantic strolls. If you need an extra layer, a blazer or trench coat will keep you warm and smarten up the look in case it runs into the evening, which is definitely a good sign!

When it comes to accessories, you can allow yourself to be a bit more daring. Accessories are a good way of injecting some personality into your look without going overboard. A statement earring or a color-popping shoe will jazz up that simple jeans and tee combo or add a bit of pizzazz to a more pared-back dress.

What to wear on a first date in the evening 

Evening dates require a little more sartorial work. A printed midi dress is my go-to, especially if I’m dashing straight from work to the date. A swankier venue may require a pair of heels too, but if I’m just hitting the pub, a pair of box-fresh sneakers will give a dress that laidback ‘I didn’t make too much effort’ edge.

If dresses aren't your thing, you can also smarten jeans up with a blouse and a pair of mules or strappy sandals. Avoid distressed detailing on your denim, and opt for darker shades if you want a dressier take. Mom jeans are flattering on all shapes, sitting high on the waist and tapering at the leg. They are super easy to dress up and down without appearing too ‘done up.’ Plus, they have a cool, vintage aesthetic that will give you a few extra fashion points.

What is the best color to wear on a first date?

There are lots of so-called rules about color when it comes to what to wear on a first date. There has even been some research that suggests men are more attracted to red, but what if that’s not your color? 

I wear a lot of green as it compliments my skin tone and matches my eyes. Smooth, I know! But the point is you know yourself best and what colors suit you. If you never wear yellow, don’t suddenly decide to wear a yellow dress. Now is not the time for experimenting! 

You might feel more comfortable in a more muted color palette. Black is a popular choice, and you can always give it a lift by adding a bright accessory or a statement shoe.

What to wear on a first date: five outfit formulas to fall in love with

I’ve rounded up the best outfit combinations that will work whatever date you’re having. So even if your date doesn’t turn out to be ‘the one,’ your outfit will be.

Blouse + Mom Jeans + Heels

Black silk Anne Bing Taylor camisole with lace trim

(Image credit: 24s)

Annie Bing Taylor Camisole

Specifications
RRP: $189/£171

Sponsored

This sexy camisole blouse will catch anyone's attention on the first date. The soft draping and strap sleeves offer a flattering and comfy fit. We love the delicate silhouette this creates but you can wear this tucked into your jeans to show off your waist. You can even get this half price in the 24s sale event that offers selected items at 50% off.

What to wear on a first date: Zara Mom Jeans

(Image credit: Zara)

Zara Mom Jeans

Specifications
RRP: $39.90/£27.99

Mom jeans are a great choice for everybody, sitting high on the waist and loose on the leg for a flattering fit. Their relaxed style makes them easy to dress up or down and comfy enough for all day wear. You’ll get plenty of wear out of these beauties from date number one to date number 100.

What to wear on a first date: & Other Stories Chunky Strap Heeled Leather Sandals

(Image credit: & Other Stories)

Specifications
RRP: $129/£85

You can’t go wrong with tan sandals, and these are guaranteed to go with everything. The block heel makes them comfy, too, so you won’t have to worry about your shoes hurting if you’re lucky enough for the date to go on for hours. Available in yellow and black, you’re probably going to want one in every color.

Shirt Dress + Trainers

What to wear on a first date: Zara Ruffled Print Dress

(Image credit: Zara)

Zara Ruffled Print Dress

Specifications
RRP: $69.90/£49.99

A shirt dress is another winner for your wardrobe, and the chic blue and white color combo on this number gives it extra style points. The flounced hem and puff sleeves add a dose of romance. Wear with white sneakers for a sporty twist that works well for more casual daytime dates.

What to wear on a first date: Veja V-10 Leather White Black Sneakers

(Image credit: Veja)

Veja V-10 Leather White Black Sneakers

Specifications
RRP: $150/£115

These sleek kicks are a smart choice that will effortlessly work with any look without stealing the attention away. The monochrome palette keeps them timeless too. As an added bonus, they are made from sustainable materials, ticking that eco-friendly box. You won’t regret investing in these.

Midi skirt + Tee + Flats

what to wear on a first date, MATCHESFASHION Toogood Bellringer Gingham Cotton-Blend Gauze Midi Skirt

(Image credit: MATCHESFASHION)

Toogood Bellringer Gingham Cotton-Blend Gauze Midi Skirt

Specifications
RRP: $1,001/£770

Sponsored

This floaty and feminine midi skirt will make dressing a breeze. A classic gingham print in a neutral color palette, it’s a strong addition to your capsule wardrobe. Stick to the pared-back palette and team with creams and browns for a chic getup. Minimal styling is needed with this standout skirt.

What to wear on a first date: J Crew Linen Crewneck T-shirt

(Image credit: J Crew)

J Crew Linen Crewneck T-shirt

Specifications
RRP: $39.50-$49-50/£44-£55

You can’t beat a crewneck t-shirt, and this linen number is a fresh take on classic cotton. An ideal layering tool, every wardrobe needs a decent white tee, and this one’s the top of our wish list. Available in 11 different colors and prints, you’re probably going to want to stock up on a few!

What to wear on a first date: Dune London Grange Snaffle Trip Loafers

(Image credit: Dune)

Dune London Grange Snaffle Trip Loafers

Specifications
RRP: $99/£75

When it comes to fancy flats, loafers are having a fashion moment. This camel pair is elegant and smart and a good choice to take you from the office to a hot date. Their low heel makes them comfy, and the gold detailing gives them a luxe touch. Stick to neutral colors, and they’ll never go out of style. 

Jeans + Tee + Blazer + Flats

What to wear on a first date: Levi’s 501 Original Fit Women’s Jeans

(Image credit: Levi's)

Levi’s 501 Original Fit Women’s Jeans

Specifications
RRP: $98/£100

Levi’s iconic 501’s still deserve a spot in your wardrobe rotation. They have a straight leg fit, giving them a more relaxed shape than figure-hugging skinnies, so they are great for dressing up or down. Crafted from 100% cotton, they have a vintage vibe that will add a cool edge to your look. Opt for darker washes for a smarter take. 

What to wear on a first date: H&M Double-breasted Jacket

(Image credit: H&M)

H&M Double-Breasted Jacket

Specifications
RRP: $49.99/£34.99

If you’ve yet to invest in a chic blazer, this one has lots of top reviews from its customers for its quality and fit. The soft pink hue gives it a feminine spring-like finish that can easily be thrown on over jeans or a dress. Perfect for smartening up your look, the lining is made from partly recycled polyester too.

What to wear on a first date: Boden Elisa Rib Top

(Image credit: Boden)

Boden Elisa Rib Top

Specifications
RRP: $65/£42

Your wardrobe may already contain a collection of stripy tops, but there’s always room for one more, and this one has some stylish elements for a modern update. The frill detailing on the neckline and the cuffs add a fun finish, and the fitted-stretch fabric makes it the perfect layering tool.

What to wear on a first date: Kurt Geiger London Otter Flat Slip on

(Image credit: Kurt Geiger)

Kurt Geiger London Otter Flat Slip On

Specifications
RRP: $165/£139

There’s nothing like some fun footwear to add a dose of personality to your look without going OTT. How adorable are these rainbow lobster mules? Perfect for jazzing up a simple jeans and top combo, the crystal embellishments and rainbow hues are sure to add an extra spring to your step.

Dress + Mid Heel

What to wear on a first date: Omnes FSC Viscose Portobello Wrap Midi Dress in Purple Animal Print

(Image credit: Omnes)

Omnes FSC Viscose Portobello Wrap Midi Dress in Purple Animal Print

Specifications
RRP: $103.50/£75

The classic wrap dress is universally flattering and easy-to-wear. The purple hue gives the animal print a fresh update as well as adding a pop of color. Crafted from Viscose, it’s super soft on the skin as well as being sustainable. Keep accessories simple when styling this statement frock.

What to wear on a first date: Iris & Ink Lucy Leather Mules

(Image credit: The Outnet)

Iris & Ink Lucy Leather Mules

Specifications
RRP: $145/£125

If you happen to be hitting a swanky bar or restaurant and need to elevate your look, then these super sleek mules are the one. The square-toe and thong design give them a contemporary edge, and their minimalist style will go with everything. Made from leather and with a block heel, they’re comfy too. 

Charlie Bell

Charlie is the Acting Deputy Fashion Editor across multiple women’s magazines and also a freelance fashion, beauty and lifestyle editor. 


She bagged her first magazine job in 2009 and has previously written for titles including Woman & Home, Closer and Dare. Over the years Charlie has embraced anything that was thrown at her from styling celebrities to testing out the best jeans on the high street to writing about must-have beauty buys. 


With a weakness for a printed midi dress, Charlie is on a mission to shop more sustainably and loves finding new ethical brands and second-hand buys. You can follow her on Instagram @fashionabell_