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5 Classy Date Night Outfit Ideas

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When it comes to fashion rules, I am generally a fan of throwing out the rule book and wearing what you want. However, dating can be stressful enough without wondering what we should wear.

For this reason, I’ll break down some of the best date night outfit ideas, how to customize them to show off personality, and why some outfits might be best avoided. 

Best Date Night Outfits

Because StitchFix puts together whole outfits, I’ve included them here. However, I should specify that these ideas are meant as inspiration.

While you can certainly utilize the talents of StitchFix’s personal shoppers, you can also use it as inspiration and find these pieces as thrift stores, online retailers, or at your nearest department store.

Of course, keep in mind that you’ll want to figure out exactly where you’re going and what you’re doing for this date night.

It’ll help you determine how casual or dressed up you should be for the occasion. It also matters how well you know this person. If this is a first date, I’ll add in a few caveats as we go.

Outfit 1: Boho Chic 

I’m a huge fan of boho chic. If this isn’t your style, you can customize it by removing the kimono shrug and adding a cardigan or leather jacket instead. In truth, this outfit is for casual date nights — especially the ones where you’ll be doing an activity.

Mini golf, bowling, an escape room, axe throwing, or even just a night out bar hopping can make a casual choice the right one. Pair your favorite jeans with a flattering top and shoes. 

If this is a first date, I’ll always recommend flats over heels simply because, as women, we’re not always sure of our safety. It’s important to meet in safe and public locations and to let other people know where we are.

We can even turn on trackers on our phones to report our location. With all that being said, it’s not unrealistic to have shoes that are comfortable enough for a fast getaway.

This might be a buzz kill when planning for your date night, but it doesn’t take a fan of true crime to recognize that dating is fraught with actual danger for women. Forego the shoes that make you teeter totter for the pair that are sexy but functional. 

Outfit 2: Body Suit, Faux Leather Pants, and Booties

If you want to turn up the heat and wow your date, consider faux leather trousers with a body suit and heeled booties. It’s a smoking hot look that manages to be casual with an edge. It doesn’t matter if you’re going out for drinks, dinner, or dancing, you’ll likely be all set to impress. 

You can add splashes of personality with a statement purse or jewelry. You can add splashes of color or go for a more neutral look.

Just remember that confidence is going to come through no matter what you’re wearing. If you’re going to be uncomfortable in outfit like this, opt for something else instead. 

Outfit 3: LBD + Color Pop

date night outfit lbd and pink blazer

I will always recommend having at least one little black dress (LBD) in your closet. It’s so versatile. And it’s classy. You can wear it anywhere and dress it up or down as needed. I’m a fan of adding a color pop when wearing the LBD.

In this case, the hot pink blazer adds a fun constrast to the all black ensemble and understated jewelry. You can also switch it up and make the shoes the statement piece or simply add a bag that gives it more personality. 

Not only is the LBD sexy, but it can work with nearly any date night outing. It’s perfect for a first date, but it can also be worn when your date night is with a long-term partner.

Keep in mind that makeup can also be where you add that color pop. Pair with bright lipstick or a smoky eye to create a flattering, memorable look.

Outfit 4: Maxi Dress and Sandals

In the northern hemisphere, Spring is coming and warmer weather is ahead. A maxi dress with sandals and a salty bag could be a fun date night outfit.

It gives off casual vibes, but it also shows that you made an effort. If “salty as a beach” doesn’t quite fit your personality, find another fun bag or statement jewelry piece to add to this ensemble. 

This is a flirty look. Don’t overthink it. Keep the makeup to a minimum, add an ankle bracelet to the sandal pairing, and go for the extra glossy lipgloss.

This is a fun summer night outing dress, a casual dinner out dress, or a loves-long-walks-on-the-beach dress. It’s feminine and just a touch understated but makes a real impression when accessorized. 

Outfit 5: Jumpsuit with Sandals

I’ve been informed that some men hate jumpsuits. That’s their perogative. Some women might hate them, too. But I’m not one of them. Jumpsuits are comfortable and almost universally flattering.

They’re especially great if they have pockets. This one is bright, flattering, adorable and perfect to pair with bright sandals. It’s a joyful outfit meant for having a fun night out on a date. If you don’t love bright colors or patterns, you’ll find plenty of jumpsuits in every style and color. 

If jumpsuits aren’t for you, ignore this entirely. Not every outfit is going to suit you. What’s most important is that you like what you’re wearing and feel good in it.

So, skip the outfit in the closet you keep promising yourself you’ll wear “one day” and go for the outfit you favor that always makes you smile. Trust me: you’ll be glad when that confidence is projected during your date night. 

Bonus: Outfits to Avoid

I generally suggest wearing whatever makes you comfortable, but I’ll add just a couple of outfits you might want to avoid for date night. Take it with a grain of salt — and perhaps a shot of tequila — but this is what I’d avoid if I was planning a date night out. 

Outfit 1: Bridesmaid’s Dress

Whatever former friend told you that you could wear that bridesmaid’s dress again lied. Most bridesmaid dresses look more like prom-wear than date night appropriate.

There are some exceptions, of course, but you don’t want to show up in formal wear for the majority of date nights — unless it’s been specified that it’s a formal occasion.

Even then, you might want to make sure that the bridesmaid’s dress in the back of your closet fits the bill. If it’s lime green and hideously ugly, a date night might not be the best time to give it a second chance. 

You might want to get more wear out of the dress you’ve only worn once, but this is not the time to say yes to that dress. Say no and find something more suitable instead. If all else fails, say yes to the little black dress.  

Outfit 2: Your Birthday Suit, Or Near Enough

I want to point out that, unfortunately, double standards exist. I loathe them and frequently complain about them, but I’m also going to say that for safety reasons, it’s a good idea not to wear clothes that are too revealing for date night.

If it’s with a long-term partner, that’s different. If it’s someone you don’t know well, beware of them thinking you owe them something for taking you out.

It’s an antiquated and offensive, misogynistic way of thinking, but we all know that there are men out there that think that way.

With that being said, if you’re meeting up to swim laps or hang out at the beach, wear your swimsuit with confidence. If, however, you’re going out for a night on the town, maybe opt for something a little less revealing until you’ve had time to assess their character in greater detail.

It’s a safety consideration that I really wish I didn’t need to recommend. Stay safe out there, ladies. 

Also, listen to the way they speak about and judge other women. There are red flags imbedded in any negative judgments about how other women look or dress.

Pay attention to that because while they might not talk that way about you, it tells you how they think — and you don’t need that kind of negativity in your life. 

When the Date Night Arrives

What’s most important for date night is that you feel comfortable and confident about how you look. If your date isn’t into you, that’s their problem. The right person is going to be attracted to you and think you’re wonderful. Does the wrong person’s opinion really matter?

Of course, it does. It hurts our feelings when someone doesn’t think we’re awesome. But what matters most is how we feel about ourselves.

Insecurities will absolutely be broadcase in how you carry yourself on this date night. So, leave those worries at home, and just show up as your wonderful, fabulous, sexy self. 

To shop the looks above or to browse the other options on StitchFix, visit their website. Otherwise, feel free to use this as inspiration.

Go out and buy something new or pull out that LBD at the back of your closet and see if you can’t assemble what you need from what you have already. Be safe, and have fun!

The Truly Charming