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Introduction

Planning an outfit for a date night can be stressful, especially if you have no idea where to start. You might be going on a casual date night and need something that screams cute but casual, or you might need an outfit that’s perfect for a fancy dinner date.

In this post we’ll be giving you some fun and versatile outfit ideas and pieces you might want to incorporate into your date night outfit. Hopefully you’ll put together a look that has you feeling confident, beautiful, and ready to have fun!

Some of these are perfect for upcoming holidays, like Valentine’s Day, while others are more suited for a casual date night, an outdoorsy date activity, or even a cozy night in!

No matter what type of date you’re going on, picking a good outfit is crucial. You want to not only look good but feel your best too. Before we dive in, here’s some key things to take into consideration when putting together your date night outfit.

Things to Consider: 

1. Weather

Many times we easily overlook the weather conditions for the sake of a good outfit. However, you’ll want to be feeling your best and be able to focus on your date, so make sure the outfit is suitable for the weather.

Now in the winter, you may want to consider having a nice coat or jacket to pair with your look. You could also make the outfit interesting with layers and remove them if you get too hot.

As the warmer months come along, make it more versatile and bring along a light sweater in case you get cold or forego it entirely if you tend to get hot more easily.

2. Date Activity

Your date location and what you’ll be doing are the two biggest indicators for what kind of outfit you should put together, as there’s often an unspoken dress code.

If you’re going to happy hour, take it into consideration when making your outfit. What you wear on a coffee date will be different from a nice dinner date. What you wear ice skating will be different than what you might wear to a concert venue.

Same thing if you plan to stay in for a cozy movie night versus go out. Don’t disregard the date activity for the sake of a cute outfit! You want to look cute but also be on theme.

If it’s a first date you definitely want to take that into a consideration since it’s the first time you might be meeting. You’ll get to make a first impression and you want your outfit to be well put together.

3. Your Comfort

​Ladies, we all know the phrase, “beauty hurts” and we love to toss it around especially when picking outfits. We’ll wear heels or an uncomfortable pair of jeans cause they’re cute even if they hurt.

But trust me, your comfort should take precedent. You want to put together an outfit that not only looks good but feels good on you and makes you look your best.

Whether you’re going for casual looks or a feminine look, style it for you. Pick some of your favorite brands to wear and take into account your personal style. The best thing you can do when picking a date outfit is put your own comfort first and stay true to yourself.

If you feel good, you’ll look good and you’ll be able to enjoy the date even more. Now that we’ve covered some things to consider for your outfit, here are twenty outfit pieces and ideas that make for perfect date looks.

1. Leather Is Always A Great Choice

First, we have leather. Some are opposed to leather, but personally, I’m a huge fan. I think it’s versatile and there’s so many great pieces you can add to your outfit to elevate it.

2. Classic Sneakers

The power of a good sneaker cannot be understated. If you want to feel incredibly comfortable on your date, wear some comfortable shoes.

Wear a pair of sneakers, white sneakers are always a great choice, and there’s so many different kinds to choose from. Whether you’re going out in the evening or doing a casual date during the day, a classic sneaker can be dressed up or down.

3. The Little Black Dress

Every woman knows the little black dress is a closet staple. If you don’t have one, it’s time to get one. The power of a little black dress cannot be ignored!

It’ll also make your life so much easier when you’re trying to pick an outfit and can’t figure out what to wear. You can probably make the classic little black dress work.

What’s great about it is that, if you have the right style, you can dress it up or dress it down making it perfect for all kind of outings.

4. Sweaters

As it’s winter, sweaters had to be included on the list. A great sweater can go a long way for date outfits.

Consider:

• cozy sweater
• sweater dress
• chunky sweater
• printed cardigan

There are so many sweater options to pick from nowadays, from classic colors, fisherman style, fun prints, etc. the world is your oyster. If you’re going on a coffee date, an oversized sweater is always a great choice paired with some simple jewelry.

If you’re going on a nicer evening date, a sweater dress is a great option, especially one that’s off the shoulder. A sweater as the base for your outfit is perfect if you’re someone who prioritizes their comfort.

5. A Slip Dress

I’ve recently become a huge fan of the slip dress. I think it’s not only incredibly cute but such a versatile option. It’s a great choice for your date night ensemble.

If you like to keep it simple, a slip dress is a great way to go. Much like the little black dress, I feel it’s an option that can be dressed up or dressed down and adjusted for any occasion.

You can pair it with a chunky sweater, leather jacket, heels, classic white sneakers, fun boots, etc. Whether you’re going on a date to the farmers market or having a classy evening dinner, a slip dress is the perfect choice.

6. Boots, Boots, And More Boots

As someone who always reaches for boots when putting together a look, I always recommend a good pair of boots. It can easily take your look from an okay outfit to a very cute outfit.

Consider:

• tall boots
• knee-high boots
• thigh-high boots
• chelsea boots
• platform boots

There’s plenty of different styles when it comes to boots that you’re sure to find something you like. I personally love platform boots and think that they put together any outfit.

Sometimes you can have a great look, but something is missing. Consider adding a pair of boots from your closet as it might bring together the whole look.

7. Fun Mini Skirt

Mini skirts never went out of style, but they’re definitely on the rise again with the resurgence of early 2000s looks.

If you love mini skirts, picking one from your closet can be a great start for building your outfit. Pick one that is both cute and comfortable as your starting point.

Then pick the top based on the date activity and the weather conditions. This will ensure your look is attuned with your own comfort but also suitable for the date itself.

8. Play With Color

Never underestimate the power of a pop of color. Sometimes all an outfit needs is the right amount of color to make it both fun and very cute.

Don’t be afraid to mix patterns or colors. Experiment a bit. If you put together an outfit that has you standing in front of the mirror questioning if it’s super cute or actually incredibly ugly, then you’re on the right track.

If you’re feeling less daring, but want some color, select a piece from your closet that has the pop of color or the look you’re going for and build the outfit around that.

9. The Oversized Blazer

For a classier look, go with an oversized blazer. The oversized blazer can immediately take the most casual look to the next level. You’ll be giving Sofia Richie Grainge with an oversized blazer.

If you want that very minimalist or clean girl aesthetic than this is a great choice for you. There’s also endless styles and colors to pick from!

10. Denim Is Your Best Friend

Denim will always be your best friend and will always make a cute date outfit. Incorporate denim with a pair of jeans, in a top, or a jacket.

You can’t go wrong with your favorite denim jeans. They’ll make you feel great and you can dress them up or dress them down depending on the top and what pair of shoes you wear.

For dressing it up, consider tall boots or heels and for dressing it down, some cool sneakers are perfect. Of course, if it’s cold out and you want to wear denim, go with a denim jacket!

11. Dressy Heels

If you’re dressing up for your date, a pair of heels is always a great option. There’s so many different high heel options that you’re sure to find a pair that feel comfortable and look good.

You can spice up a more causal outfit of jeans and a cute top with heels or take a nice dress to the next level.

12. Accessories Are Your Ally

You can make a simple outfit the perfect outfit with some accessories. Accessories go a long way when it comes to putting together an outfit.

Consider:

• jewlery
• bags
• hats
• scarves
• belts

Simple accessories can carry an entire look and change the tone of it as well. If you want something light and feminine go with a delicate necklace. Pick interesting earrings or a statement accessory to add a bold touch to your look.

Don’t dismiss what purse you pick or if it’s cold out what hat or scarf you wear. It can tie your whole outfit together. Always take into account if gold jewelry or silver jewelry works best with your skin tone!

13. Matching Sets

For the lazy girls who just don’t have the energy to brainstorm an outfit, no worries. Matching sets are your new best friend.

Whether you want to wear pants or a skirt, a matching set is a great option to consider. There’s so many cute styles out there, and it’s perfect for those who don’t want to overthink their look.

14. Dress Pants

Dress pants are often overlooked, but they’re a perfect balance for when you want to dress up your outfit without making your top or shoes fancier. The key here is the material.

Consider a material that’s much nicer like velvet, linen, suede, etc. The right material can make your pants much fancier and make it easier for you to keep the rest of the outfit fairly simple without compromising its quality.

15. Simple Tops Go A Long Way 

A simple top can carry your look. What’s important to consider, much like dress pants, is the material. Think silk, satin, and sultry textures.

A favorite of mine is silk tanks or something lacy. Romantic tops are a great choice and can be paired with any style bottom. If you have a top you definitely want to wear, build the look around that.

16. Comfortable Shoes

If you want to wear comfortable shoes but not sneakers, don’t worry you have options!

Consider:

• strappy sandals
• ballet flats
• mary janes
• uggs

Depending on your date you might be able to wear a cute pair of uggs. But if it’s something nicer or a day date consider some cute strappy sandals or ballet flats with a pair of frilly socks!

17. Skirts

I’m a skirt girl through and through so I always reach for a skirt when going on a date. Again, you have so many options. Start with the length. Do you want a a maxi, midi, or mini?

Then pick the style. Do you want a denim skirt? Something flowy and loose? Something whimsigothic or cottagecore? There’s so many options.

Narrow down your choices by answering some of these questions and then build the whole outfit around it!

​18. Long Coat

For the winter girlies, a long coat can truly add to your look! Go with a trench coat or an edgy leather duster or a nice wool coat.

No matter what you pick, it can change the mood of your outfit so make sure it pairs well with what you’re wearing!

19. The Casual Look

Sometimes a date might be super casual as in tshirt and leggings casual which makes picking an outfit all the easier, but still put some thought into it!

A graphic t-shirt is always a great option or some kind off the off shoulder shirt. Pair it with nice leggings or comfy sweats and you’ll look effortlessly cute and cozy.

Don’t forget some fun socks!

20. Cute Mini Dress 

Finally, a mini dress is always a great choice. Come Spring, start pulling out your mini dresses!

It’s an easy and simple way to pick an outfit. If there’s a dress that makes you feel pretty and comfortable pick that one for your date!

Have Fun!

A date at the end of the day is about quality time. You’re there to spend time with the other person and get to know one another. Whether it’s a special occasion or a casual date night, you want to make a good impression and have the perfect outfit for the occasion.

You want to feel the best version of yourself especially if you’re feeling out of your comfort zone. So don’t forget to take into account your own style and comfort. We hope you put together a cute date outfit with our help and have so much fun!

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