What to Wear on a First Date

Welcome to your ultimate guide for what to wear on a first date for men and women.

For men, it’s best not to take too many risks. Just wear something well-fitted and well-ironed. For women, it’s all about finding the gap between glamorous and casual without overdoing it in any of these two categories.  

Below, you’ll find a short summary of what makes a good first date outfit for men and women. There’s also recommendations for purchases you can make to spice up your outfit for your next first date. Simply, click the links for an affordable example of each item, listed for sale on Amazon.  

The Number One Rule for First Date Outfits

The number one rule for first date outfits is to wear something suitable for your environment.

If you’re outdoors, you’ll need to wear something suitable for the temperature. If you’re heading somewhere formal, you’ll surely want to dress somewhat formally. If you’re doing some sort of sporting activity, you’ll need suitable clothes and footwear for that.

There are plenty of cultures who prioritise looking good over being comfortable on first dates or big nights out – but that really is dumb. 

If your outfit makes you uncomfortable in any way, that’s going to affect your ability to enjoy the date and show off your best self to the other person on the date.

Showing your best self is far more important than what you wear, if you’re looking to impress your date and make them want to see you again. That’s why wearing something suitable for the environment is your number one rule.

What Should Men Wear On A First Date?

This guide is going to assume that the date venue is some sort of casual cafe or bar. It’s not too formal, nor is it particularly cold.

This is the type of first date venue recommended in our beginner’s guide to dating. These venues create a low-pressure environment likely to convince nervous men and women that it’s worth turning up and giving this other person a shot. 

So, what type of outfit should a man wear to blow this woman away?

Well, honestly, the best bet for a man is not to take too many risks.

A lot of women are quick to disqualify men for polarising style choices that they decide they don’t like. So. it’s best not to be polarising with your outfit.

Instead, you’re better off going with timeless classics that aren’t going to put anyone off. 

On top of that make sure your shoes are clean, your clothes are well-ironed and that your grooming is on point. If you turn up looking scruffy, a woman is going to sense you don’t know (or care) enough to be able to take care of yourself – and that can be a real turn-off.

With that said, here are some reliable wardrobe items that’ll serve you well.     

1. A Well-Fitted Dress Shirt and Jeans

The original and arguably still the best choice for a first date. A well-ironed and well-fitted dress shirt will never look out of place. Add a trusty pair of Chelsea boots and you’re ready to rock. Check out this sky blue checked short-sleeved shirt from Pierre Cardin, as an example.  

2. Leather Jacket With White Tee and Jeans

This outfit is somehow as popular now, as it was when John Travolta rocked it in Grease all those years ago. There’s just something about leather jackets that scream ‘fun bad boy’. How about this black jacket paired with a plain white t-shirt and jeans?  

3. Blazer Jacket with Jeans

Pair a blazer jacket for a plain white t-shirt, jeans and sneakers for instant smart-casual success. You’ll look classy, sophisticated yet relaxed at the same time. This checked navy blazer from Joe Browns could blow her away. 

4. Textured Trousers and Suede Bomber

A suede bomber and textured trousers are another combination that will bring instant smart-casual success. Pair it with a button down shirt and you’ll be dressed to impress wherever you decide to invite your beau. It’ll come off like you’ve made an effort without overdoing it, and that’s exactly the vibe you want to portray. 

5. Denim Shirts, White T-shirt and Dark-Washed Jeans

Denim shirts have been in style for a long time and that doesn’t look like changing any time soon. Add a white t-shirt, your favorite pair of dark-washed jeans and Chelsea boots and you’ll be ready to sweep any lady off her feet. 

6. Popular Indie Band T-Shirt and Ripped Jeans

It’s a look that will always attract that alternative Indie girl and plenty of others too, so embrace it. Stick with universally popular indie bands like The Strokes or The Arctic Monkeys. Ripped jeans can be a risky choice, but not if you’re going for the dreamy indie frontman look. 

What Should Women Wear On A First Date?

Stereotypically, women are more likely to stress over a first date outfit compared to men. Perhaps, rightly so.

Men are more visually-motivated when it comes to attraction, after all. Plus, a lot of women are prone to feeling more confident when they think they look beautiful.

So, how much effort should a woman put into her appearance on a first date? 

Well, as already explained, it’s important to consider where your date is going to be. Instead of feeling like an absolute bombshell, you might feel a bit uncomfortable and embarrassed if you consider yourself overdressed for the venue.

A lot of guys might not find it a huge turn-on if you show as much skin as you would in a nightclub on Friday night either, especially if he’s invited you to a cafe on a Tuesday afternoon.

Below are half a dozen reliable wardrobe items that will impress a man on a casual first date.

1. Simple White Dress Paired With Edgy Leather Jacket 

If a white dress on its own feels like a bit much for a first date, slip on a badass leather jacket for some added edginess. 

Monochrome is a timeless classic, which will seemingly never go out of style, and it seems like leather jackets are going to be the same way. 

This black faux-leather jacket provides an affordable yet stylish edition to your wardrobe, if you don’t already have a real one.  

2. Full-Length Pleated Summer Dress With Sleeves And Pockets 

A party dress on its own might seem like a bit much for a first date, but if you take a look at this full-length summer dress with sleeves and pockets, you might change your mind. It’s effortlessly feminine and oozes class while remaining relatively affordable. 

3. Floral Trousers And Black Tank

Similar to the first two editions on the list, this combo matches a simple item with a statement item, all while remaining classy and feminine. These floral trousers are suave, sophisticated and suitable for any casual first date that you’re invited on. 

4. Off-The-Shoulder Dress and Ripped Jeans

Ripped jeans are another item that are casual, edy and a tiny bit revealing without being trashy. This royal blue off-the shoulder dress will go fantastically well with any pair of ripped-jeans.

5. Blue Lacy Floral Dress 

Floral dresses always look fantastically feminine, either when worn on their own in summer, or paired with tights or jeans in colder months. This blue button-down floral dress is a personal favorite, which will surely go fantastically well with pumps or high heels. 

6. Satin Midi Dress

Satin Midi Dresses are always a great choice for a first date, either on warm weekend afternoons or paired with jeans for cooler evenings at the bar. How about this bright red number paired with your favorite lipstick and chunky jewellery? Does this scream bombshell or what? 

What If It’s Going To Be Cold? 

If it’s going to be cold in your home city and you’re likely to be outside for even a short while, you might want to consider the outfits suggested in our guides on fall date outfits and winter date outfits

Final Thoughts  

Ultimately, the best outfit you can wear on a first date is one that makes you feel confident. Confidence is regarded as one of the sexiest personality traits, after all.

With that said, following the guidelines and the outfit suggestions listed above will help you make a sensible outfit selection the majority of the time. 

Remember, the links in the article above will all lead you to an affordable example of each item. So, why not splash out on a new purchase today?