What to Wear on a First Date for Any Occasion

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

Feminine, Sexy and Smart

Picking cute date outfits for a first date can be just as stressful as the date itself. Should you wear heels or flats? Pleated skirt, shorts, or 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.

Casual date outfit

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 booties, 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 appreciated for you to saunter in with pajama pants and flip flops.

Dinner date outfit

Now this 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 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 flats at home. You don’t need sky-high stilettos to look good. In fact, sometimes it can be too much. However, classy two-inch heels will give you more elegance than any pair of flats can hope to accomplish.

Outdoor date outfit

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 to highlight just one asset, 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 want to keep warm and comfortable, but try to wear something form-fitting that accentuates your figure, and if it’s too cold for any outdoor date outfit that requires no less than three layers and that oversized jacket, consider taking the date indoors.

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 or to bundle up so much in the winter that you look like the marshmallow man.

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. Again, it bears repeating: 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.

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 them 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 not only match with your cute date outfits, though, but also to choose the accessories that illuminate your natural tones. For example, maybe turquoise earrings would go better with your eyes instead of ruby earrings. And be careful not to overdo it and go crazy with too many accessories!

Looking for singles in your area? Visit our local dating page to locate professional singles near you today!

Masculine, Sophisticated and Charming

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, but women do appreciate a man with a personal style. The following tips will help you nail that first date outfit.

Casual date outfit

You don’t need to do anything 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. 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 (and even then, maybe consider dialing it down for one day).

Dinner date outfit

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. 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 – Leave the loud, witty T-shirts at home. You’re not an aging rock star clinging to his youth. And please put the baseball caps away.

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.

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.

And that’s it!

Be practical. Choosing what to wear on a first date doesn’t need to be difficult. 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. The goal is to be confident being your best self in order to focus more on making the date engaging and fun. And for goodness sake, if you need to suck in your gut to keep your outfit from ripping apart, don’t wear it. Ever.