Whether you’re going on a first date or your regular date night, you’ll want to look and feel great. Putting together a stylish outfit is a sure way of giving you that extra bit of confidence. The right clothes will make you walk and talk with conviction.

But deciding what to wear on a date can be difficult. Firstly, it depends on what you’re doing – and what stage of the relationship you’re at.



What to wear on a first date

Scenario: Going for a meal or drinks


One of the first things you’ll notice about an individual is their outfit. It’s a bit like personal branding – you can tell a lot about a person by what they’re wearing and they’ll be having a close look at your outfit choices too. Indeed, there are few other occasions where such first impressions matter as much as a first date. So take your time and choose carefully.



If you’ve arranged to go for a meal or drinks, you’ll want to look smart – but not like you’ve rushed straight from work. For guys, putting on a shirt shows you’ve made a bit more effort, but don’t worry about a tie or jacket. When choosing what to wear on a date, you’re looking to bridge the gap between smart and casual.

But it’s not as hard as it sounds. A shirt with some colour or a pattern to show your personality will be the right balance. We love a plain shirt but with a patterned placket to show a bit of your personality like this Claudio Lugli Light Pink Botanical Shirt.

If it’s cold, consider taking a jumper with you instead of your work jacket – Luke 1977 have a great range to suit all tastes.

You’ll want to impress from head to toe too, so don’t neglect what you’re going to wear on your feet. We always find that quality and ever-lasting style trumps trends when it comes to men’s shoes. You can’t get much better than the range from Hudson Footwear – Chelsea boots are so hot right now, check them out for all their quality leather shoes, loafers and boots.



"A man should look as if he had bought his clothes with intelligence, put them on with care and then forgotten all about them."
Hardy Amies


For girls, it’s hard to go wrong with a great dress on a first date. Lavish Alice has some that will definitely create a lasting impression – this yellow wrap front dress, for example. Feeling indecisive? It also comes in white, so you have options.

If the weather isn’t looking great, Lavish Alice have some trendy capes to cover up with. Choose a timeless colour such as black and you’ll wear it time and time again – so even if that first date doesn’t work out well, you’ll still have a great jacket.

Alternatively, you could go for jeans and heeled boots teamed with a stylish top. Don’t think it’s a boring look – yes, it’s a go-to outfit choice for many but it works for a reason. This Bellfield Twist Front top is a great option for a smart casual look which you will comfortable and confident in.

Don’t forget accessories either. A nice scarf could complement your outfit for example. But always bear in mind the saying ‘less is more’ – don’t overload on accessories just because you’re not sure what works.





What to wear on a second date

Scenario: Taking on a fun date activity


You shouldn’t be so nervous on the second date. But that doesn’t mean you can take your eye off the ball. You’ll still need to impress when deciding what to wear on a date, even if the first went well. If you’re doing an activity – like bowling or crazy golf – your outfit needs to be more casual, but you’ve got to keep up the same effort.



Guys should think about jeans or chinos with a polo shirt. It’s a classic look that’s versatile and flexible. For example, a long sleeved polo such as this solid colour one from Luke 1977 would look great with a pair of darker jeans like these Luke 1977 Vacuum Indigo jeans which also have elastic in them so they are easy to move around in!

It’s less about what brand, and more about how well the clothes fit you. Make sure you get a cut of jean that suits you. They’re a wardrobe staple so it’s worth spending a bit of time and money getting the right pair.



Do you go for an A-line skirt or skinny jeans with a relaxed fitting jumper? It’s most important to feel like yourself and comfortablein your outfit – so that will help you eliminate a few options.

There are a few ideas that suit most shapes, though. We love this shirt and cardigan combination from Bellfield. Wear them with a high waisted skirt or blue jeans – whatever complements your style best.

The same principle goes for what you wear to keep warm. It’s got to suit you. Depending on how you’re feeling, you might stick to the cardigan, or go for an on-trend satin bomber or a timeless denim jacket.


"Today everybody can look chic in inexpensive clothes (the rich buy them too). There is good clothing design on every level today. You can be the chicest thing in the world in a T-shirt and jeans – it’s up to you."
Karl Lagerfeld




What to wear on a regular date night

Scenario: Date night


Just because you’ve been together a while, this doesn’t mean you should neglect dates. Inject a bit of excitement into your week and plan some time away from Netflix. With the right date night outfit, you’ll be ready to turn up looking amazing and have a great time with your partner – even if you’ve been on 48 before.


On your first few dates, it’s probably not the best time to experiment with a new style. But now you’re comfortable with each other and can happily discuss what you’re wearing, it’s a great time to try something new and get an honest opinion from someone you trust.

There are some relatively easy ways to test your comfort zone. For example, you could try some patterned shirts like this floral Claudio Lugli Shirt or try a cut and sew grandad collar from Luke 1977.

On the date, take a smart coat or jacket with you and treat your date to some cocktails in a nearby bar. This camel coat from one of our favourite brands, Luke 1977, for instance, will add a refined touch to any look. Every guy needs a go-to coat in their wardrobe that they can return to each year when the colder weather returns.




For girls, the ever-popular jumpsuit is a way of being a bit more adventurous. Now that you know each other better, it won’t matter if you take that little bit longer in the loo getting it on and off (great style isn’t always convenient).

This Lavish Alice jumpsuit will catch his eye with an abstract print. Chuck an easy-to-wear duster coat over the top and you’ll be sure to impress. This cream Bellfield one would look fantastic with the Lavish Alice jumpsuit– and the rest of your wardrobe.

You could also consider adding a bit of statement jewellery to your outfit. It’s an easy but effective way of dressing up something simple. A great necklace, for example, can also refresh outfits you’ve worn before. Again, our go-to brand is ICHI who have this gorgeous gunmetal necklace.




The essential dos and don’ts for what to wear on a date



- Above all, do make sure you feel comfortable and confident in what you’re wearing

- Do try your outfit on before the day, especially if you’re buying something new

- Do have a back-up outfit in mind

- If you’re in doubt, do ask someone for a second opinion (it helps if you like their style)

- Do check out the venue online beforehand to get a feel of the vibe

- Do make sure your outfit is clean and fresh



- Don’t be afraid to show some personality

- Don’t ignore the occasion – you’ll look like a muppet if you turn up for a walk in the park dressed for a dinner date

- Keep the mystery and don’t show off too much skin – this goes equally for men and women, low V-necks don’t look good on anyone

- Don’t panic – if you’re in doubt, just wear your favourite things

- Don’t overdo the make-up or styling products

If you’re having any problems deciding what to wear, or just want another opinion before your date, you can pop into our store in West Malling. We’ll be there to offer some friendly advice on what looks great on you.



FAQs on what to wear for a date


For the meantime, here are some of the questions we get asked the most – and how we typically respond.



Are there any styles I should avoid?

Yes – these include: slogan t-shirts, overly tight shirts, and anything that’s seen better days. Scruffy, worn-out clothes are never a good look.

What shoes should I wear?

The same goes for shoes – ones that are a bit dishevelled will just ruin the rest of your outfit. But then it depends on what you’re doing. If you’re going out to a fancy restaurant, put on your suit shoes or a pair of smart brogues.

Desert boots are also great – they could easily take you from a walk in the park to a quick drink afterwards. For casual activities, smart trainers will look best. Whatever the activity, just remember to make sure your shoes are clean and smart.

Where can I easily pick up style tips?

Even if it doesn’t come naturally to you, don’t worry – you can easily pick up style tips from other guys. Take a look at their outfits and how they have put the different elements together. If you like the look, there’s no crime in trying something similar.

Who knows – if the first date goes well, your date might be taking you shopping and giving you tips before long.


"I've been quite a late developer on the clothes front, but I've suddenly realised it is one of life's joys."
Benedict Cumberbatch




What advice do you have for tall girls? Heels or no heels?

If you’re someone who always wears heels, whatever your height, you’re probably going to feel more comfortable wearing them. So go for that. However, if you’re just as happy in a pair of stylish flats, think about the date activity more and make a decision on that.

Activities where it’s better to wear flats include: a walk in the park, bowling (otherwise they’ll give you those ugly bowling shoes), and casual brunch.

How do I plan what to wear for a day date?

As if dates weren’t a minefield enough, those in the daytime are full of confusion. You could just meet for two hours for lunch. Or it could be an all-day exploration of galleries, coffee shops, bars and whatever other shenanigans.

The best advice we have is to wear comfortable shoes that are smart enough for a fancy bar and to wear layers – that way, you can adapt depending on where you end up.

What make-up tips do you have?

Generally, guys don’t really seem to get make-up. So keep it simple – if you’re going for a statement lipstick, don’t also go overboard on eye make-up and vice versa. Take a few essentials in your bag so you can re-apply in the toilets if you need.


Have you got more questions? Come in and speak to us, not an automated service, and we’ll help you with all of your fashion queries.