The eternal question for those playing the dating game: what should you wear the first time you go out with someone? If you dress too formal, you’ll end up looking like you’re at a job interview. If you dress too casually, you might look like you’re taking the date very seriously — plus, everyone wants to look their best. There is clearly a lot to consider when it comes to picking the perfect first date ‘fit.

The best first date outfits will take into consideration each unique body, accentuating its strengths, while still being modest enough to let personality shine. For women, good choices include knits, simple dresses, eye-catching tops, and even elevated basics. Go with whatever provides confidence.

Of course, as much as we all wish it were true, you can’t just pop on any old number and head out for your date. The entire outfit must be considered, from season to setting, there is a lot to factor in. Stay with us as we go over all the details you need to know to look like a star on your first date — paparazzi not included. 

Choosing What to Wear on a First Date

Picking out an outfit can seem like an impossible task, where should you even begin? Well, a good place to start is in front of your closet. What do you already have and what does it say about your sense of style? You’ll want to capture your essence so that you’re able to give your date a true portrait of your style. Plus, you don’t want your date feeling catfished on a more casual date. You should also investigate where your date will be taking place so that you can be sure that your outfit will match the atmosphere. To elaborate, if there is a dress code, be sure to match it. Additionally, if you are going to a trampoline park, you are obviously won’t go with the cocktail dress option. Assess where you are going and make the best decision for the date activity.


Once you know what vibe you’re trying to achieve, it’s time to look in the mirror. This part can be scary, but we’re only looking for the positives. Have great shoulders from all that extra yoga? Wear a nice off-the-shoulder top to show them off. Proud of your new bike routine and the resulting toned thighs? A ruffled romper can be a great way to show off those gams. Long story short, wear clothing that shows off your best attributes and gives you confidence.

Structured Tops

Never overlook the power of a good top. Based on versatility alone, a good top can be the right choice for many types of dates. Keep the following in mind when deciding on a top for your first date: 


  • Avoid Busy Patterns: You want your date’s attention to be on you, not on the pattern of your shirt. You can help by avoiding any overly crazy patterns. While your screen-printed cat shirt is truly eye-catching, and could be a good way to get a good laugh in, it isn’t very date-appropriate;
  • Modest Cut: How far is too far when it comes to a top’s plunge? Well, take a look at Zoe Kravitz in this Oscar de la Renta gown and you’ll get a good idea of what to avoid. After all, you want your date to be focus on you – not your assets;
  • Pair Appropriately: Don’t forget that you will need an appropriate bottom to match your top. These bottoms could be anything from a pencil skirt to a nice pair of jeans. 


Whether it is sweater weather or not, when it comes to knits, don’t hold back! Not only are knits comfy and cute, but they are also versatile and great for a wide range of body types or occasions. A neutral-colored sweater will be suitable for most dinner dates, and when paired with the right accessories, can be a casual-chic choice of apparel. 


Don’t underestimate the power of a cute dress. The right dress can be a powerful signifier of your style and taste, along with being traditionally feminine. Modest dresses are a great way to be sure that you’ll match the atmosphere of almost any occasion. If the more recent revival of the prairie dress has proved anything, it’s that being covered can be cool! 

Elevated Basics

When in doubt, go simple. Tried and true combos, such as jeans and a t-shirt, are a great basic option. If you’re meeting up for coffee in a park, throw on a blazer and you have a simple and comfortable outfit that matches the casual surroundings. Even something as simple as a low-backed camisole can look elegant when paired with the right accessories. Keep patterns simple, such as polka dots, to avoid looking too over-the-top. 

Last Tip

Still staring at your wardrobe and feeling lost? We have one final tip. Choose an outfit you remember receiving a compliment the last time you wore it, this is a sure-fire way to pick something that will give you confidence when you wear it—and that is what really matters!