What To Wear on a Date: A Guide for Women

What To Wear on a Date: A Guide for Women

Dating can be exciting, but sometimes it can also be nerve-wracking! There’s a lot to think about and look forward to, but having the right outfit can help alleviate some of that stress so you can focus on having a good time and getting to know this new person. We’ve all been there, trust me. 

Don’t fret. I am here to give you the ultimate guide on things you can wear on a first date that will help you look and feel your best. I have the answers to some fashion questions that you may be trying to answer right now as you have your closet scattered all over your bedroom floor.

I got you: Let’s dive into some date night outfit ideas that make a strong first impression.

Should I Accessorize for a First Date? 

Yes, but less is more, even when it comes to trendy accessories. Accessorizing can really bring a cute outfit together and help give some subtle personal details to your clothing as well. First-date looks might not be the best fit for trying out something new.

They are trying to get to know you. Pick accessories that you wear on a normal basis that highlight what you are all about. Don’t go overboard for a casual coffee date, but keep it personal.

Dress or Pants? Which Is Better for a First Date? 

I think this all depends on, of course, you and your personal preference, but also make sure to note the venue. If your first date activity is going to be a walk in the park and a picnic, you may not want to wear your most luxurious black dress and high heels.

Or if you are eating out at a fancy restaurant with an explicit dress code, jeans and a shirt may not fly. Basically, note if a venue has a specific dress code and plan accordingly.

Aside from that, it also depends on the date itself and whatever you feel best in. Both dresses and pants can be great options for a first date when styled correctly. This same question can apply to what shoes you wear on a first date.

Again, keep in mind what activities or events are going to be happening and plan accordingly always. Remember to wear whatever makes you feel best, whether that's a dress or pants. 

How To Style a Pair of Pants for a First Date 

There are a few ways you can go about this that are equally as chic and fashionable. My go-to (if dress code appropriate) for a low-key, casual date is a simple but stylish pair of straight-legged jeans.

Straight-legged jeans are the perfect combo of the “boyfriend” jeans and a classic pair of skinny jeans. These go perfectly with a ton of tops, from button-downs to t-shirts, and are great for lots of different occasions too. 


What To Wear on a Date: A Guide for Women

Shirts with big collars, chunky sweaters, bodysuits, or even a loose shirt look flawless on straight-legged jeans. Straight-legged jeans are considered a “universal” style, meaning they look chic on everybody and every body type!

If you want to go for this look for a chill dinner date, keep the outfit simple and use this opportunity to add in some of those personal accessories like statement earrings or classic loafers. Pair this look with an oversized coat or blazer, and you’ve got yourself a first-date outfit idea that is versatile as it is fashionable. 

How To Style a Dress for a First Date 

How to style your dress will all come down again to the venue and the activity, but I’ve got some tips that will work for whatever your date has planned.

Dresses are a fan favorite for a variety of reasons. They are comfortable and cute and can instantly make you look and feel like you are dressed up and ready to go, even without accessories or a nice leather jacket. 

Styling Dresses for Spring/Summer


What To Wear on a Date: A Guide for Women

Styling dresses for a spring or summertime outdoor date might feel nerve-wracking, but creating a new outfit for this occasion is more simple than you may think. You will want to avoid heavy articles of clothing or shoes and focus on keeping your clothes lightweight and breathable.

With the sun shining down, you don’t want to be weighed down by your outfit in the spring and summer months. I prefer a flowy sundress with a plunging neckline, a wide-brimmed hat, and a cute pair of booties or sandals that you can easily kick-off for some fun in the sun. Keep your accessories dainty so as not to overpower your outfit. 

Focus on lighter or neutral colors as well when you are planning this outfit. Have your pop of color be the lightweight, bright denim jacket you add in case of wind. Or, add in some sparkling eye shadow or dramatic makeup for a glimmer. 

If you want to have a pattern highlighted in this outfit, stick to something simple like stripes or small dots, or even find a dress with some patterned texture. Your spring or summer first date will be a breeze when you style yourself this way. 

Styling Dresses for Fall/Winter

Layering is your friend when it comes to styling dresses in the fall or winter. This is the perfect opportunity to add some clothing accessories like a jacket or coat, scarf, tights or leggings, and high boots.

There are lots of different ways that you can add some warmth and style to your dress for the fall or winter. One of my favorite ways to do this is by adding a turtleneck under a babydoll-style dress or a maxi slip dress. It instantly helps add warmth to your outfit but also can help give your dress a retro vibe that is cute and approachable. 

If turtlenecks aren't your thing, consider adding a chunky sweater over either of these dresses for a comfy and cute look that is as functional as it is fashionable. This incorporates a pattern or pop of color that may not have been present before.

You can never go wrong with a pop of color, especially in the wintertime when most outfits are neutrals or dark. Add a splash of purple, red, or even dark green with this outfit in the form of a sweater or cardigan. 

Show Off You

No matter what you end up wearing on your first date, the most important thing is to just be yourself. Wear clothes that help you look and feel like YOU. Remember that you wear the clothes, not the other way around. Don’t get so hung up on your outfit that you forget that the best part of your outfit will always be you.

Your date is excited to get to know you and your personality, not the clothes you wear. Bottom line, wear whatever makes you feel beautiful and confident because you are! Whether that is a pair of jeans or a fitted dress, pick an outfit that highlights and shows off all the best parts of you. Happy dating!


What to Wear on a First Date? We Asked the Experts! | The Every Girl 

15 Makeup Looks That Are Perfect For Your Next Date Night | Glam

The 20 best first date ideas, according to relationship experts | Today

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