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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.

By Nicola Gabriella One Shoulder Midi Dress

The By Nicola Gabriella One Shoulder Midi Dress is a beautiful linen maxi dress. This dress is super versatile as it can be dressed up or down. As a casual linen style, this dress makes the perfect effortless look for a casual date over coffee. This style is available in colours pink grapefruit and sunkissed orange.

Alemais Songbird Mini Dress

The Alemais Songbird Mini Dress is a gorgeous button up mini dress in a stunning floral print. This dress features balloon sleeves, accent lace detailing and an ivory cotton rope to cinch at the waist. This romantic style can be dressed up or down, which if made more casual paired with sandals or sneakers, is perfect for a casual first date. This comfortable style brings playful and flirty vibes which nails the first date outfit brief.

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.

Sir The Label Rei Knot Dress

The Sir The Label Rei Knot Dress is a gorgeous linen style that features an on trend cut out at the waist with a knotted tie on the waist and shoulder. In a beautiful beige with rusted orange floral print, this dress looks gorgeous on all skin tones and hair colours. Linen styles are great for daytime, more casual events such as going out for lunch on a first date.

Aje Caliente Tiered Cut Out Dress

The Aje Caliente Tiered Cut Out Dress is an asymmetric midi dress in a beautiful daisy yellow colour. This linen dress is perfect for a more casual event as it is as formal yet still makes you look put-together. The daisy yellow is perfect for the summer season and this dress exudes elegance and sophistication. Although this style is dressier, this stunning dress makes the perfect daytime event outfit, that suits a cocktail dress code. If your date is taking you to a fancier place for lunch, this dress is your go-to.

Rebecca Vallance Catania Mini Dress

The Rebecca Vallance Catania Mini Dress is made from a linen blend and features a floral print, puff sleeves, side pockets and an open back. This mini dress is perfect for the spring/summer season as it is easy to wear and makes the perfect outdoor dress. Wear this number to a daytime event such as a lunch date, with heels to make it semi-formal or sandals to tone it down.

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.

L'idee Theatre Mini Dress

The L'idee Theatre Mini Dress is a super unique, fun and playful style especially for if you are needing a dress for a drinks date. This dress features a fitted waist and flared umbrella skirt which gives a flattering silhouette, as well as a rounded neckline and soft flared sleeves for a touch of elegance. This dress is sure to turn heads, especially with its stunning midnight blue colour, which is exactly what you want in making a good impression on a first date!

Sir The Label Ambroise Knot Dress

The Sir The Label Ambroise Knot Dress is a sleeveless midi dress featuring a cut out at the waist and a knotted tie at the waist and shoulder. In a gorgeous floral print, this dress is the perfect first date outfit during the warmer seasons. With colourful florals, your date will have all eyes on you, especially with the fun and flirty cut-outs at the waist. A stunning dress suitable for all bars and restaurants.

Aje Gracious Cut Out Dress

The Aje Gracious Cut Out Dress is a stunning mini that exudes elegance and femininity. This dress features a frill skirt and voluminous shoulders which are offset by a cut-out and back tie. In a beautiful bright orange, this dress makes the perfect summer outfit for a drinks date. Pair this gorgeous mini dress with some sandals or wedge heels to elevate the look.

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.

Arcina Ori Aston Dress

The Arcina Ori Aston Dress is a gorgeous long sleeve dress that is perfect for events on a cooler night. Featuring a wrap around design with cut outs, this dress is extremely flattering and unique. The Aston Dress is made from a thick ribbed material that provides extra warmth. This gorgeous long sleeve dress is sexy and elegant, which makes it the perfect dinner date outfit for if your wanting to make a good first impression.

Zimmermann Aliane Ruffle Midi Dress

The Zimmermann Aliane Ruffle Midi Dress is crafted from linen and cotton. The dress features a self tie bow detail at the front and ruffled trimming alongside the shoulders, leading to a racerback with cut-out details. In the warm orange colour, this dress is perfect for night-time and day-time events in the warmer seasons. We love this linen fabric as it adds a sense of luxury, yet still perfect for a dinner date. This dress will have you feeling comfortable and confident which is all you need in a first date outfit.

House Of CB Isabella Corset & Lila Skirt

The Isabella Corset & Lila Skirt is a gorgeous mermaid inspired two piece formal outfit. In this beautiful bright jade colour, this style is guaranteed to suit all skin tones and hair colours. This elegant two piece set features a corseted bodice to accentuate an hourglass figure, floaty ruffled sleeves and a dreamy flowing skirt. This two piece set is extremely versatile as it can be worn to plenty of events such as date nights, birthdays, fancy lunches, cocktail parties and formals.
We love this style for fancy dinner dates, as you are guaranteed to make a great first impression.

Nookie Eleganza Midi Dress

The Nookie Eleganza Midi Dress is a beautiful off the shoulder style with puff sleeves. This dress is perfect for dinner dates as it is simple and elegant but still unique with the sleeve feature. This form fitting dress is extremely flattering on the figure and will definitely make a statement on a first date. Simple, but sexy, this style is suitable for all skin tones, hair colours and age groups.

Finding Your Fit

Struggling to make the items in your wardrobe work for you? You can hire all of the pieces featured in this guide here. With our convenient hiring system, you'll never have to outfit repeat again, and you will have a much wider range of styles to choose from within your budget.

Hiring an outfit is a much more sustainable way to shop, and your purse will thank you too.


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