What to Wear on A First Date



So, you’ve got a first date lined up. Cue the stomach-churning, jelly legs, a little perspiration, and — let’s face it — a momentary influx of panic. In the lead-up to a first date, you’ll probably find yourself viewing the items in your wardrobe in a whole new light; read: through the eyes of your date. Is that dress too much? Is it just me or is my favourite shirt actually insanely unflattering? What possessed me to buy those jeans in the first place? Finding the balance between effortlessly cool and polished can feel impossible in the midst of an ‘I have nothing to wear’ pre-date breakdown. If you’re not sure where to start, we’ve got you covered. Take a few deep breaths and read on to for our top tips on what to wear on a first date, depending on where you’re headed. 

Things To Remember

When it comes to picking an outfit for a first date, taking these three things into consideration will guarantee a head-turning look (no matter what you’re actually wearing).

Confidence Is Key

It’s a bit cliche, but that’s because it’s true. No matter what you’ve got on, wearing it with confidence is really what brings a look together. That means absolutely no negative self-talk — talk to yourself like you would to a friend heading out on a first date. Would you tell your friend they look terrible and undateable? We didn’t think so.

Confidence is also largely communicated through body language, so think about how you’re holding yourself. Start by rolling your shoulders up and back, and keeping your gaze up and forward. The bonus? Even though you might be feeling some first-date jitters, you can actually trick your brain and body into feeling calm and controlled by assuming a confident stance. 

Stick To Silhouettes You’re Comfortable In

Comfort is key on a first date, and by that, we don’t mean slipping into an old hoodie and leggings — although, if the location calls for it, why not? On a first date, we recommend opting for a silhouette you feel comfortable in. Perhaps you feel your best in all things oversized, or you’re at your most confident in a form-fitting mini dress. Whatever your style, stick to tried and true silhouettes that you’ve felt great in before.

Go For Practical Accessories

While mini bags and strappy stilettos are always a crowd-pleaser, they may not be the most practical accessories for a first date. If you’re comfortable in stilettos and they’re your usual go-to then definitely stick with them, but if wearing sky-high heels leads to an awkward stumble (or five) and aching feet, step out in something else. Mules are a great substitute for a more formal date, while chic white sneakers, leather loafers, or classic sandals are perfect for casual settings. As for a bag, make sure you have enough space for everything you need. A crossbody bag is effortlessly wearable and most styles will fit all the essentials. 

What Not To Wear On A First Date

We don’t really prescribe to the idea that there are any absolute ‘don’ts’ when you’re putting together a first-date outfit. As long as you feel comfortable, confident, and you’ve got everything you need with you, you can’t really go wrong. However, we do recommend avoiding the following on a first date.

Don’t Wear Brand New Items 

A first date is probably not the ideal time to experiment with any items you haven’t worn before. To eliminate any risk of any last-minute outfit disasters, it’s best to opt for pieces that have been worn in, even if you’ve just put them on around the house. You definitely don’t want to be settling into a dinner date before realising your rigid denim jeans have absolutely no give, or that those brand new leather boots are blister-breeders. Stick to items you’ve worn at least once so that you know exactly how they fit and feel. 

Don’t Wear Something That Doesn’t Feel Like You 

Before the first date, you may find yourself scrambling to pull together an outfit you think your date will like, even if it doesn’t make you feel like yourself. Or, you might feel tempted to emulate the style of someone you think is desirable. While sourcing inspiration from others is a great way to refresh your wardrobe and feel on-trend, it’s important that your outfit still speaks to who you are and what you’re about. Remember, your date wants to get to know you — if you’re trying to be someone else, the experience will probably be disappointing for both of you. 

What To Wear On A First Date

Below, we break down our recommendations for what to wear on a first date depending on what the plan is. 

A Casual Date

So, you’re heading out on a casual date. Think coffee, a picnic, a movie, or an activity, like mini-golf. When it comes to what to wear on a casual first date, you’ll want to find something that feels comfortable but looks put together. During warmer months, wrap-style mini dresses and smock dresses are ideal. Team your dress with sandals for a breezy feminine look, or opt for runners to style the dress down a bit.

If dresses aren’t your thing or if there’s a chill in the air, look to wide-leg jeans and an oversized tee or shirt. To elevate your look and make it date-ready, team this classic combo with loafers, some timeless gold jewellery, and perhaps a simple shoulder or crossbody bag. This will create a chic yet understated look, perfect for more relaxed date locations.

A Lunch Date

For lunch dates, we love a printed midi dress or a floaty skirt with a plain white tee. If it’s warm, bright colours and prints work best for daytime dates. In cooler months, you can swap out your colourful midi dress or skirt for one in an earthy tone. Knit fabrications also work well when it’s cold, and pair back easily with boots or sneakers.

For those who prefer to wear pants, a lunch date calls for relaxed trousers and a tee or chunky knit, depending on the weather. Full-length, oversized trousers paired with sneakers makes for an on-trend outfit, while tapered cropped pants and loafers deliver a classic look.

A Drinks Date

If you’re making your way out to a bar for drinks on your first date, you can afford to go with something a little more ‘dressed up’. A mini dress with balloon sleeves or a bold print works well for drinks dates. If the bar is particularly sophisticated, a sleek pants-and-crop set will be ideal. Throw an oversized blazer over your shoulders for extra style points (and warmth!).

For your drinks date, a pair of comfy heels are a go-to. We love mules or low strappy heels in bold colours. If your outfit is colourful or printed, opt for neutral accessories and vice versa. While contrast colour blocking is effective, combining too many different prints and clashing colours tends to look messy. If you’re more comfortable in flats, leather-look slides or sandals are perfect for a bar setting.

A Dinner Date

A dinner date is arguably the most formal date option, although the choice of venue will determine which way to go with your outfit. Dinner dates at formal restaurants will require something a bit more refined. For an elevated contemporary look, look to a blazer and pants combo. If you’re after something with a traditionally feminine flair, a slip dress is a timeless and foolproof option. Jewel and neutral tones work well for evening dates, but you could also mix up your outfit by having a statement pop of colour somewhere.

As for what to wear to a more informal dinner date venue like a pub, we suggest going for structured styles that can be easily dressed down. We’re loving jumpsuits, which can look a little more laidback than a dress while still offering a streamlined, sophisticated silhouette. Jumpsuits are also particularly good choices for dinner dates in winter. The head-to-toe design will keep you comfy and warm, and they tend to pair back well with a classic leather jacket.


 Struggling to make the items in your wardrobe work for you? You can hire all of the pieces featured in this guide here. If you do opt to hire an outfit for your date, remember to wear it around the house for a bit before you head out. Hiring an outfit is a much more sustainable way to shop, and your purse will thank you too.

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