What to Wear on a First Date?

Just as work attire can make or break a day in the office, selecting what to wear on a first date might just turn a good date into a great one, making a world of difference to your confidence and possibly the opportunity for a second date.

Every detail – from the cut of a jacket to the choice of accessories – can speak volumes about your personality and style. Dressing for a first date is less about adhering to rigid norms and more about showcasing your best self. 

Let us guide you through some style tips and outfit ideas for selecting the perfect ensemble that boosts your confidence and charm, making every first impression count.

What to Wear on Different Date Settings

Since the pandemic our approach to dating has changed – a time when virtual dates became a new norm – gone are the days of dinner dates being the only date idea. Now, a virtual date is often a precursor to the first in-person meeting, and with rising living costs affecting how some choose to date, activities like walks or a quick drink are becoming more common.

However you choose to meet someone for the first time, it can be useful to have a few options in mind for what to wear to make a good first impression. Below are some of our recommendations for different date settings:

What to Wear on a Coffee Date

A coffee date is a great option for a relaxed, casual first introduction. And, with London not short of cosy, ambient cafes, a coffee shop date is easily accessible for those of us with a packed schedule. Attire should be comfortable for you personally, erring on the side of causal. 

• For men, a merino wool sweater or a casual button-down from brands such as Fred Perry, coupled with some dark jeans from Reiss, offers a polished yet approachable look.
• For women, a casual, chic ensemble can portray the best image, such as a luxury knit top paired with premium jeans from Frame, finished with ankle boots from L.K. Bennet.

What to Wear on a Date for Drinks

The first date activity most recommended by our matchmakers is heading to a bar or lounge for a drink or two. This allows for a casual, time-defined meetup while still offering the chance to put your best foot forward and get a good sense of who your date is. In these cases, an outfit that blends comfort with an edge of refinement is best. 

• For women, a chic silk blouse paired with high-waisted trousers offers a smart yet relaxed look. Brands like Max Mara and Armani offer options for both. 
• For men, an up-and-coming brand like Percival, or a classic label such as Paul Smith, are reliable choices to strike a balance between relaxed and refined.

What to Wear on a Lunch Date

A lunch date – or even a weekend brunch – is arguably one step forward from meeting for coffee, when you’re feeling more confident to spend a little more time with your date. The vibe will likely be as relaxed as a coffee date, with a touch more formality.

• For women, a dress from Reiss or a chic blouse from Hobbs, paired with some white jeans, for example, offer contemporary elegance.
• For men, a smart-casual ensemble, such as a blazer and trousers from Burberry or Paul Smith, paired with a soft patterned shirt from Charles Tyrwhitt, can work wonders. 

What to Wear on a First Date for a Walk

Outdoor dates, such as a simple walk through your nearest green space (think St James’, Holland Park or even a canalside stroll) are an excellent option for a relaxed first introduction. Out in the open air, and with no pressure to sit face-to-face like at a dinner table, a short, casual amble is also easy to fit into your busy weekday diary. Of course, dates in the great outdoors call for attire which is stylish, comfortable and, above all, suitable for the weather. 

• For men, a Barbour jacket paired with comfortable chinos from Oliver Spencer is a good option. For practical footwear, opt for some Hunter wellies for wetter weather or stylish Veja trainers for dry conditions.
• For women, a waterproof Barbour or Burberry jacket will keep you dry whatever the weather. For a casual, comfort-first look for a walk in the park, some sports leggings from Lululemon will offer ease of movement. 

What to Wear on a Date to Dinner

If you do choose to go on a dinner date for your first meeting, it can offer a chance to really impress with your chosen outfit. Depending on where you opt to dine, tailor the formality of your outfit accordingly – and don’t forget the power of your signature perfume or aftershave to communicate who you are.

• For women, there is a whole range of brands to be inspired by, from Temperley London to Self Portrait. Accessories also tie an outfit together, with brands such as Mulberry and Jimmy Choo adding a touch of glamour.
• For men, fine dining establishments offer an excellent opportunity to don a well-tailored suit from Savile Row. Colours like navy or grey are timeless, but choose the shade you feel most yourself in. A pair of Oxfords are perfect to complete your look, suited and booted.

Tips for Professionals from Stylist Deni Kiro

While we all have our favourite brands which make us feel fantastic, styling yourself for a date is also about knowing what really suits you, your body and your personality. Deni shared some of her pillars for timeless style that will carry you through any first date.

Your Style Personality

Start with understating what your style personality is and what sort of image you want to portray on your date. It’s important that the clothes you wear make you feel like the best version of yourself. To express yourself with clothes, think what style you want to portray, whether it’s modern, romantic, classic or creative.

‘If you want to appear modern on your first date, I advise you to go for a sleek minimalistic look. For an effortless look, mix & match structured tailoring with a soft jumper. Tonal dressing is a great idea for petite ladies, to elongate the silhouette. Dress head-to-toe in one colour and pick wide-leg high-waisted trousers styled with block heels to make your legs appear extra long.

 

‘When I consult clients on discovering or elevating their style personality, I always consider the client’s natural energy – for example, if you have a girly or lady-like natural energy, I recommend choosing clothes that bring opposing contrast such as minimalist or contemporary style. Remember that fashion is a tool and it has an influence on both the wearer and the observer. It’s all about creating the right first impression that reflects your true self and style.’

Dress for Your Body Shape & Complexion

When getting ready for a first date it’s important to consider what fit suits your body shape and what colours flatter your skin complexion. Start by answering the question ‘Which parts of your body do you love the most? Is it your legs, waist or neckline?’ Decide on which part of your body makes you feel confident and select pieces that accentuate it. 

‘Avoid oversized clothes or too-tight pieces and instead opt for that one piece that fits you immaculately. Using a tailor to alter the length of your trousers and waist will take your look from good to great.

 

‘When deciding on colours, think about the shades that make your face shine. Picking the right shades for you is important as it can help brighten up your face, whereas the wrong colours may bring darkness to your face and make you look tired. A quick test to check if a colour suits you is to look in the mirror and check if people first notice your face or the colour is too strong and overpowers your features.’

Dress for the Date Venue

An important aspect of a first date is the venue you will be going to before your date, it’s important to always check the venue location online to pick your outfit accordingly. 

‘My advice is to check the venue on Instagram and coordinate your outfit with the environment to avoid looking overdressed or underdressed.

‘For a dressy dinner, pick intricate fabrics and smart cuts. If you want to come across as creative, opt for intricate prints and play with colours. Nothing beats a killer dress in a feminine print and elegant heels. Everyone looks more elegant in heels and finding a comfortable pair is important so you feel relaxed on your first date. I recommend exploring heeled boots as they offer more support in comparison to the stilettos.’

 

Transforming Your Work Look to Your Date Look

For those who need to go from work to their date, Deni has just the right tips for you. Many of our clients make this transition when meeting a match and we always recommend changing from work clothes if possible, prompting your mindset to shift from work to leisure. 

‘You can transform your work look into a dating look for the evening with a few key elements. If your workwear is more formal it can be softened by switching your trousers for smart jeans and chandelier earrings. Adding a few statement accessories or changing your shoes is also a great way of transitioning your workwear to your date wear.

‘To make an impactful impression opt for original colours and statement details and show some personality through your look on your first date.’

 

Dress for First Date Success

When choosing what to wear – and what not to wear – on a first date, focus on selecting the right fit, quality fabrics, and interesting accessories. Find the right balance in your look, whether it’s a smart-casual mix & match or a minimalistic look with a colour accent, it’s important to reflect on your natural self, channelling your professional energy but tailoring it to the occasion: an exciting time to connect with someone exceptional.

Take the first step towards truly compatible dating by contacting our exclusive, high-end matchmaking specialists today.

If you are interested in booking a personal styling consultation to get ready for your first date you can do so by visiting www.denikiro.com. You can book a ‘define my style’ online consultation to evaluate your style personality or get styled in-store or online from any part of the world. For those who are looking for a complete wardrobe revamp we also do style makeovers.