A Woman's Guide to How to Dress for a Casual First Date

How to Dress Casually to Impress

Image courtesy of 31 Outfit Ideas First Dates

Imagine this; you just got asked out on a date to a local coffee shop, now what? All sorts of thoughts begin to run through your head. What should I wear? Do I have anything cute? Do I need to go out and buy a new outfit? These thoughts, among many others, may cross your mind.

If you find yourself guilty of having had these thoughts before, take a deep breath and now exhale, you have come to the right place. As you read on, you will learn different tips on how to best dress to impress your date casually without going out and buying a whole new wardrobe. For some, it is easy to find something cute yet casual to wear. While others, despite having multiple outfits to choose from, still struggle to find the “right” thing to wear.

Guess it’s time to throw in the rag and cancel your date. After all, you can’t go out in public naked, can you? But, of course, you can; you just wouldn’t want to deal with its consequences.

If the previously mentioned thoughts have crossed your mind, the first thing you need to do is take a step back. But unfortunately, going on a first date with this kind of mindset is one of the best ways to cause a disaster before an event has occurred.

Before you continue reading, get up, grab yourself some water, coffee, or tea, and find somewhere cozy to sit. Comfortable? Good, because in this how-to article, we’re going to discuss:

• How to dress for a casual first date
• Ways you can dress simply and cute at the same time!
• How your outfit (and first impression) can help lead you to a second date

 After all, you may as well make yourself comfortable as you continue reading about how to dress for a casual first date. You should continue reading to see the various possibilities of dressing simple yet cute, making such a great first impression that your date will want to see you again.

What Do I Already Own?

Time to see what you already have waiting for you in your closet!

As butterflies fly around in your stomach, you make your way into your room to take inventory of what you have hanging in your closet. Sifting through your clothes, you find shirts and dresses that you had completely forgotten that you owned. It’s crazy to realize just how many things we just shove into the back of our closets and forget that we own. 

Since you already know that the date will be casual, you can automatically skip over all formal attire. However, this should still leave you with a handful of options. After taking inventory of what you have to choose from, the next step of getting ready for your date is determining what you want to wear. If you find yourself in a pinch and can’t find anything that you like, then you can go ahead and shop around a store that sells casual clothing, such as Target, Kohls, and H&M, to name a few. 

What to Wear? 

When in doubt, recruit friends for help!

Whether in person or via video calls, your friends got your back, and you can count on them to give the brutally honest truth about what they think of an outfit before you decide what it is that you want to wear. Of course, any good friend would like you to feel good about what you wear when going out with someone new for the first time.

When picking out an outfit for your date, you need to consider what you and your date will be doing and what the weather will permit you to wear. For example, is your date outdoors or indoors? Are you doing something physical like playing a sport or riding rides at an amusement park; or meeting up for dinner at a nearby restaurant?  These are a few essential questions to ask yourself as you prepare for your date. Below you will find a guide on the various clothing items to consider depending on the season and the colors individuals often wear during that particular time.

Clothing Items and Colors Based on the Seasons

Spring Outfits for a Casual First Date

Although warmer weather, bringing a sweater for late-night dates never hurts. Warm days often lead to cool nights. Spring clothing colors include Reds, Pink, Yellows, Greens, Blues, Purples, Whites, and Blacks.

• Dresses (floral patterns)
• T-shirts
• Quarter length shirts
• Jeans
• Sweaters
• Skirts
• Sandals
• Flats
• Converse/Vans
• Blouse
• Camisole etc.

Summer Outfits for a Casual First Date

‍ It is time to say goodbye to long-sleeve items and hello to short-sleeves! After months of cooler weather, you can now bring out your tank tops, skirts, and shorts. Summer clothing colors: Whites, Yellows, Reds, Oranges, Pinks, Blues, Turquoise, and Fuchsia.

• Tank Tops
• T-shirts
• Jeans
• Jean Shorts
• Crop tops
• Skirts
• Romper/Jumpsuits
• Summer Dresses
• Sandals
• Converse/Vans etc.

Fall Outfits for a Casual First Date

Depending on where you live, you may have to layer the clothing you have decided to wear. Fall clothing colors include Burgundy, Tans, Whites, Purples, Greys, Blacks, Oranges, and Reds.

• Sweaters
• T-shirts
• Quarter Sleeve Shirts
• Lightweight Long Sleeve
• Jeans
• Leggings
• Heeled Boots
• Converse/Vans
• Tennis Shoes etc.

Winter Outfits for a Casual First Date

Keep in mind that you will likely be layering the items of clothing that you are wearing on your date. Winter clothing colors include Whites, Creams, Browns, Blacks, Medium/Dark Greys, Dark Reds, Dark Purples, Emerald Green, and Sapphire Blue.

• Jumpsuits
• Pants
• Jeans
• Long Sleeve Tops
• Quarter Sleeve Shirts
• Boots ( they can be for rain, snow, or even just for style and comfort)
• Converse/Vans
• Scarves
• Beanies etc.

Choosing an Outfit that Gives you Confidence

This is by far an essential part of getting ready. Choosing an outfit that makes you feel confident will show that confidence outwardly to the rest of the world. And will make you appear that much more attractive to your date.

Now that you have looked at what you own and bought the items you need to complete the potential look you are going for, it is time to choose what outfit gives you the most confidence. Confidence is vital when it comes to meeting someone for the first time. You don’t want to feel so uncomfortable with what you are wearing that it causes you to pull at what you have on. Feeling uncomfortable will automatically bring down your confidence level, which will be noticeable to whoever you meet. 

Topping Off Your Outfit

Accessories accessories accessories galore! Time to top off your look and go out on your date!

The fun part is picking accessories to go along with your outfit. You may find this final step to dressing casually for a first date more effortless than others. Before even beginning, what do we mean when we will accessorize an outfit? To accessorize means adding a complementary garment with an accessory. When in doubt, it is better to under-accessorize than it is to over-accessorize.

Now when choosing what type of accessory, keep in mind that there are several options, including:

• Bags
• Shoes
• Jewelry
• Scarves
• Watches
• Wraps, Shawls, or Cardigans
• Hats
• Sunglasses and Eyewear
• Belts
• Tights/Leggings etc.

Just like it is when trying to find an outfit where you may pour all your jewelry, bags, and shoes out of your closet to try on different variations with your outfit of choice. After all, you want to dress to impress.

In the end, try not to stress. Dressing up for casual first dates allows you and your date to have fun without the added stress of dressing in your finest and permits flexibility in the activities you can go out and do together.