What to wear on a first date: our top tips for looking (and feeling) great!

Woman in alluring red dress with a glass of wine on a date

We all know the cliché movie montage where the girl tries on outfit after outfit in anticipation of her first date, but the truth is that men worry about how they look, too (although, have you noticed how some of the worst offenders seem to be the ones who worry the least?).

But, for those wondering what to wear on a first date – fear not! We’ve compiled a list of things to consider for both men and women to help you choose a first date outfit for any occasion.

What to wear on a first date: tips for women

So you’ve found a date – but picking cute date outfits for a first date can be just as stressful as the date itself. Should you wear heels or flats? Fitted skirt, smart dress, skinny jeans? And how in the world do you even coordinate jewelry anyway? Sometimes it’s understandable to be envious of men. Surely, they’ve got it easy. (We’ll get to why that’s not true later.) The first step to narrowing down what to wear on a first date is to figure out the setting for the date so that you can dress for the occasion, and then it’s just a matter of following a few simple guidelines.

Woman on a casual first date

Casual first date outfits

Meeting for coffee means you’ll be in a more relaxed setting compared to other dates, so go for something casual and stylish. The key is to look effortless, a feat we all know is easier said than done. This date should reflect what you would normally wear on a day-to-day basis, meaning you should definitely stay in your comfort zone. This is not the time to try something new or wear expensive designer brands to show off. Instead, go for the girl-next-door look by letting your hair down and wearing the cute date outfits you know you look good in. It doesn’t matter if that means jeans or a skirt, a swing dress or a sweater, flats or boots, just so long as you’re comfortable and feel confident.

What not to wear – That being said, you don’t want to come across as too confident, and that goes for both extremes. This is not the right time to show off that little black cocktail dress and six-inch heels, nor will it be ok for you to saunter in with pajama pants and flip flops.

Dinner date outfits

An elegant, ritzy date night is the right time for that black cocktail dress that shows off your figure and flashes those sexy legs. But be careful not to show too much skin. Ideally, and this goes for any first date, you’ll want to choose only one asset and highlight that, especially with your dinner date outfit. For example, if you do go for a short dress, you’ll want to keep your arms covered so they won’t compete for attention down below. Or if you want to accentuate your chest, wear a dress that at least reaches your knees or opt instead for form-fitting pants. Finally, add some elegant high heels to complete your ensemble.

What not to wear – Skip the shorts and leave your scuffed-up flats at home. You don’t need sky-high stilettos to look good (in fact, sometimes it can be too much) but a nice pair of kitten heels can add elegance. That said, if you’re not comfortable in heels, opt for some elegant flats – just avoid anything resembling a sneaker!

Outdoor date outfits

Not every date will be at a café or restaurant. Sometimes the best dates happen outside, such as having a picnic in a park or going to a ball game or even strolling through a farmers’ market. Remember though, it’s hard to feel attractive if you’re cold or sunburned, so if you’re going to go for shorts to show off your legs, consider wearing a lightweight cardigan and sun hat. During the winter, you’ll want to keep warm and comfortable, of course, but consider wearing something elegant underneath your layers – you may well want to take your date into a café to warm up afterwards!

What not to wear – Of course, you should dress according to the weather, but that doesn’t mean to don a bikini top and short-shorts during a hot summer’s day (sunburn isn’t a great look on anyone!) or to bundle up so much in the winter that you can’t be seen beneath your torque, parka, and layers of scarves.

Don’t forget: makeup and jewelry

Makeup can be tricky. How much is too much? Some women prefer to go au naturel and others like to make their eyes pop with plenty of eyeliner and mascara, so there are no hard and fast rules here, other than to stay in your comfort zone. If you don’t normally apply a lot of makeup, don’t start now in an effort to impress your date. You’ll want to feel confident, and it’s difficult to do that when you feel the need to run to a mirror every five minutes – instead, wear what makes you feel attractive, and the confidence will follow.

Jewelry can be that little, extra final touch that turns ordinary cute date outfits into stunning ones. Jewelry catches and leads the eye, so use it to bring attention to those assets you want to highlight. If you opted to wear something with a low neckline, wearing a big brooch or ornamental necklace would be the best way to focus all eyes on that part of your anatomy. It is important to match with your carefully chosen first date outfit, though, so be careful to co-ordinate.

What not to wear In our survey of first date deal-breakers, Canadian singles revealed that too much jewelry is a definite no-no. In fact, nearly a third of Canadian men (and one-in five women) think elaborate jewelry is best avoided,1 so it might be best follow in the footsteps of Coco Chanel and take one item off before leaving the house!

ABOVE ALL: Wear what makes you feel relaxed – 84% of Canadians think that the ideal first date is a casual one2 so it’s fine to wear a first date outfit that lets you feel more comfortable (and helps you focus on your date!).

What to wear on a first date: tips for men

Men have it easy, right? All that’s needed is a clean button-up shirt, nice slacks, and maybe a sports jacket if you’re going somewhere fancy. And that’s it, isn’t it? Well, not exactly. (For example, did you even notice we didn’t mention shoes yet?) An uncomfortable majority of men think fashion need not apply to them. Yes, your personality should ultimately be the deciding factor in what to wear on a first date, but women do appreciate a man with a personal style. The following tips will help you nail that first date outfit.

Man and woman on an elegant first date

Casual date outfit

You don’t need to do anything overtly fancy here. Be yourself and be comfortable, but by all means, be put together, too. Avoid wrinkled clothes, too-snug shirts or sweaters, and too-short pants. Un-scuffed sneakers are fine, although loafers or chukkas might be better, depending on whether you’re wearing jeans or khakis, respectively. For up top, you can’t go wrong with a clean button-up shirt, but a simple T-shirt and sport coat combo can add a certain flair of sophistication to your casual date outfit, as well.

What not to wear – Flip flops are a no-no. And while a sport coat is good, avoid that sports jersey unless you’re going to a game with your date afterwards. Above all though, leave your comedy slogan t-shirt at home: ‘funny’ shirts are considered the biggest first date outfit no-no there is, putting off 63% of Canadian singles.3

Dinner date outfit

A romantic dinner date is the time to make yourself feel suave but, if you’re going to go for a suit, then make sure it’s a good fit. A jacket that is too big tells your date you can’t dress yourself or that you borrowed it from someone else, neither of which gives a good impression. You can still wear jeans, just so long as they are a uniform, dark color and not faded or torn, but slacks are the better bet. However, do leave the sneakers at home. A pair of Oxfords or wingtip shoes would do you well here, and you may think it doesn’t matter, but ditch the white socks in favor of something that will blend in well with your pants.

What not to wear – You don’t need to wear a tux to a dinner date at a fancy restaurant. In fact, please don’t, not unless it’s a special banquet with a black tie dress code. Still, it’s better to err on the side of formality – so definitely leave your baseball cap and flannel shirts at home.

Outdoor date outfit

Planning a romantic picnic for your date? A light-colored button-up shirt with the sleeves rolled up is pretty much a guaranteed good look for any guy. Consider wearing a casual pair of moccasins that can easily be slipped on and off in case you and your date would like to feel the grass under your bare feet. If you anticipate a chilly evening, wear a jacket over a sweater so that you can be chivalrous and offer up your jacket without getting cold yourself.

What not to wear – Any loose-fitting tank top with the intention of showing off your muscles. Don’t be that guy. Women don’t like that guy. Plus, just as with women, sunburn just isn’t sexy. In the winter, make sure to think about what you’re wearing under your parka – you never know when the cold will mean your date has to switch from an outdoor adventure to a warm, indoor, bar or restaurant evening!

Don’t forget: grooming

A well-maintained look goes beyond the clothes you wear. If you can’t remember the last time you got a haircut, it might be time to consider getting one before your date. Also, while big beards do seem to be ‘in’ these days, that doesn’t mean you should look like you’ve been stranded on an island for months. Get rid of any stray hairs to give it that clean, sophisticated look. And don’t be afraid to do a little trimming or plucking, either. Trust us, the girls will be more appreciative than judgmental if your eyebrows are not pointing in every direction.

ABOVE ALL: If you want your first date to turn into a second, it’s ok to keep your outfit casual. Just remember to keep it on the put-together side – so t-shirts are fine (but not one with slogans), jeans are ok (but avoid ripped ones), and it’s just fine to wear casual footwear (as long as it’s neat!).

What to wear on a first date: advice for everyone

Choosing what to wear on a first date doesn’t need to be difficult, although it’s worth putting some thought into the matter. After all, clothes don’t define who you are, but they do say something about you, so don’t try to fit in to something that’s not you.

Ultimately, the goal is to find a first date outfit that will help you feel poised, confident, and attractive. So here are three things that can help you do just that:

1. Wear something that fits
If you’re constantly pulling down your skirt or sucking in your gut, you’ll have a hard time focusing on your date. And that’s no fun for anyone.

2. Dress to the occasion
A ball gown in a cafe looks just as silly as hiking boots in a fine restaurant. If possible, find out the date location in advance so you can dress accordingly.

3. Pay attention to your accessories
Whether it’s earrings that make your eyes sparkle or polished brogues that streamline your look from top to toe, the right accessories can be the flourish that perfects your first date outfit.

EliteSingles editorial January 2016

If you have any insight into what to wear on a first date, let us know in the comment section or get in touch with us at [email protected]


1,2,3 EliteSingles ‘Dating Dealbreakers’ survey 2016. Sample size: 1,000 Canadian men and women.

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