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

wondering what to wear on a first date, use these street style shots as inspiration
(Image credit: Getty)

Aa situation that can make you nervous, nailing what to wear on a first date can help with your confidence. An opportunity to show off your personality and to make that all important first impression, we've compiled some first date outfit formulas that won't let you down.

In an age of technology, a first date is often the very first meeting between you and a potential love match, thanks to the explosion of dating apps, meaning what to wear on a first date carries a lot of pressure. But don't fear, chances are you have a capsule wardrobe full of items that can easily be styled for a first date. From your best jeans to the best dresses, whatever you decide to wear on a first date, there’s one key thing to remember, 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. 

Avoid anything ill-fitting, from clingy tops that you always end up fidgeting with to shoes that rub, as you'll spend the whole evening feeling self-conscious and fiddling with your outfit, which is never a good look. If you want to ensure your clothes sit properly, you might want to invest in the best shapewear or a new bra as the right foundations ensure your clothes will fit better and you'll feel your best too. 

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 a stylish top to wear with jeans is a fail-safe option. It's a good idea to wear comfortable flats too, just in case there are any impromptu romantic strolls. If you need an extra layer, a blazer or your best 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 from any of the best jewelry brands or a color-popping shoe will jazz up that simple jeans and best t-shirt 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 effort. A printed midi dress is great, especially if you're heading to your date straight from the office. A swankier venue may require a pair of heels too - check out the best designer heels for some inspo, but if you're just hitting the pub or a local bar, box-fresh sneakers will give a dress that laidback, ‘I didn’t make too much effort’ finish.

If dresses aren't your thing, try darker washed jeans without any distressed details, with a pretty blouse and a pair of mules or strappy sandals. The best mom jeans are flattering on all shapes, sitting high on the waist and tapering at the leg. They are super easy to dress up or 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? 

The spring/summer fashion trends 2023 have dished up a lot of great trends, with color still being a key player when it comes to the season ahead. Opt for mood-boosting brights if you want to really make a splash, or at the very least add a pop of bold color to your outfit through an accessory. Wearing color suggest confidence and that's key for what to wear on a first date. Some of the fashion color trends 2023 include blue and orange hues, as well as all shades of pink.

Wondering what colors suit me? When it comes to selecting the best color for you, it's all about the proximity to your face. If you don't think red is your hue, but really want to wear the color, opt for red skirt, pants or shoes as this is far enough away from your face to still work for you. 

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

We’ve rounded up the best first date outfit combinations that will look great, wherever the night takes you. So even if your date doesn’t turn out to be ‘the one,’ at least your outfit will be.

1. Blazer + Jeans

what to wear on a first date street style blazer and jeans

(Image credit: Getty)

What you need…

When a suit feels too stuffy for a date, opt for a blazer and jeans combo instead. The blazer will add instant polish to denim whilst the jeans will keep the look feeling more lowkey. You can keep the shoes casual and opt for a pair of the best white trainers for a daytime stroll or switch to a sleek sandal for a dressier date.

A styling tip…

Inject some personality into this look and add a fun accessory such as a chic scarf or statement bag. Or opt for a bright colored blazer to lift the look.

Our fashion editor recommends…

2. Dress + Casual Flats

what to wear on a first date street style dress and flats

(Image credit: Getty)

What you need…

  • Statement dress
  • White trainers
  • Cute clutch

This look is perfect for a springtime date. A statement dress is an instant outfit maker and the casual shoes give it an effortless edge. Perfect if you’re getting ready in a hurry, it needs minimal styling, just add a fun clutch and some delicate jewelry. You can always add the best leather jacket for an extra layer.

A styling tip…

Stick to longer-length dresses that are easy to sit down in. Floaty, A-line styles work best, offering a flattering and feminine silhouette that’s comfortable too.

Our fashion editor recommends…

3. Blouse + Jeans

what to wear on a first date street style jeans and a blouse

(Image credit: Getty)

What you need…

  • Your best jeans
  • A fancy blouse
  • Comfortable heels

If dresses aren’t your thing, this is another easy look that has maximum impact, with minimum effort. You can keep it sleek and understated in a classic striped shirt, or be more daring in a bolder print or fancy embellishments. Keeping the focus firmly on your top half, it’s a great one for dinner dates where the rest of your look may be hidden under the table!

A styling tip…

Wondering how to style high waisted jeans? Tuck in your top or opt for a cropped blouse to show off the waist.

Our fashion editor recommends…

4. Skirt + Cute Knit

what to wear on a first date street style knit and skirt

(Image credit: Getty)

What you need…

Mixing a more casual item with something dressier is a fail-safe formula for a pulled-together look that doesn’t scream “I spent hours getting ready”. A pleated or A-line skirt is super flattering and feminine. Pair with the best cashmere sweater for an extra luxe touch and finish with an elegant accessory.

A styling tip…

Both heels and flats look great with this look so it’s up to you how dressy you want to go. Comfortable flats, such as a sleek loafer - a big shoe trend for 2023, is a stylish choice, for keeping the look smart.

Our fashion editor recommends…

5. Dress + Mid Heel

what to wear on a first date street style dress and heel

(Image credit: Getty)

What you need…

Some dates, such as evening cocktails or dinner may require something a little dressier, which is when this combo steps in. Stick to classic cuts such as a wrap or shirt dress that nip in at the waist for a flattering silhouette.

A styling tip…

Comfort is key so unless you’re used to wearing sky-high heels, look to a block heel or low kitten heel instead. They look just as smart but can be a lot more wearable.

Our fashion editor recommends…

What should you not wear on a first date

When it comes to first date outfits, avoid anything with holes or stains. Opt for clothing you're comfortable in, as you don't want to be tugging at your outfit all night, or stumbling in a pair of heels that are too high. Remember confidence is key and if you wear a tried and tested outfit formula, you'll be able to think more about your date and enjoying yourself, and less about whether your outfit works in that given moment. 

Is it ok to wear jeans on a first date

Of course, the answer to this question lies in what the activity of your first date is. For casual day dates, or dates at laidback venues such as a bowling alley, then jeans and a nice top is the perfect outfit combination. You can choose any shade of jean too. 

However, if you're going on a dinner date, to a smart venue or bar, it might be best to swap jeans for smart trousers, or a pretty midi dress to better fit the location. In some instances, depending on the venue, you can wear black jeans, as these provide added polish to a look. 

In all instances, it is probably best to err on the side of caution and not wear jeans that have too much in the way of distressed detailing, as opting for a slightly more polished finish will always ensure you look more put together.

Charlie Bell

Charlie is the Deputy Fashion Editor at Future plc across multiple women’s magazines including Woman & Home, Woman and Woman's Own.

She bagged her first magazine job in 2009 and has previously written for titles including Stylist, 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.