What To Wear on a First Date: 6 Outfit Ideas

What To Wear on a First Date: 6 Outfit Ideas

Don’t worry… we’ve all been there. I can picture it now:

Clothes scattered all over the bedroom floor, rushing to get out the door and still with “nothing to wear.” You’re going on a first date with a new person; you are no longer excited but rushed and stressed about what to wear. Well, that’s where I come in. 

I’m here to dish out the style tips that help you feel like your best self. 

First impressions are a big deal. In the case of a first date, a first impression is crucial. I have compiled the ultimate list of the best first-date outfits for any occasion or season.

Ultimately, the best thing to wear on a first date is whatever is going to make you feel fully confident and at your best… but if you need a little help figuring out what exactly that is, look no further! I’ve got you.

Here are six outfit ideas for your next first date to really make a fabulous impression. 


Spring/Summer Date Outfit Ideas

If you are playing the dating field in the springtime or the summertime, it’s good to have a frame of reference for the different activities and outfit trends of the sunny seasons. There is so much to do, and most of it will be outside in the sunshine.

It’s a good idea to have outfits that are both functional and fashionable. I’ve got you covered. Here are three quick and easy spring and summer date outfit ideas to take on your next sunny adventure. 


The Picnic Date Outfit

What To Wear on a First Date: 6 Outfit Ideas

If you are going on a first date and you decide to have a picnic (first of all, cute!) but it’s probably a good idea to wear something fashionable AND functional.

My top pick? A long simple flowy maxi dress and some strappy sandals that you can easily kick off to lounge on the grass. Bring a denim jacket or cardigan in case the weather is chillier than you expected. 

If dresses aren’t your style, you can never go wrong with a low-key, ruffle blouse and shorts combo to finish off the look and high-fashion sandals as well. Enjoy the summer breeze and the warm rays of the sun, and look amazing while you do it. 


The Sightseeing Date Outfit

If you live in a big city or close to it, sightseeing is always a fab first date to get to know each other better and the city you live in. For this date, you’re going to want to find some chic yet supportive walking shoes. 

I personally recommend a clean pair of white sneakers paired with a romper or linen jumpsuit with a fitted bodice. It’s flirty and comfy and will let you explore with ease. Rompers or jumpsuits are easy because they are all one piece. They give your look an effortless, classic look for any activity. 


The Farmer’s Market Date Outfit

Cameron Cotton Dress


One of the best casual first dates is the Farmer’s Market, especially when flaunting a breezy sundress (mini dress or midi dress — your choice). Having pockets is also a bright idea to hold your money for spending on local goodies.

If you can’t find a sundress with pockets, you can never go wrong with a big tote bag to store all your new local treasures in. I recommend finding one from somewhere local to support local businesses and reduce waste.

Finally, slip on some comfy shoes that match your personal style. Or, you can always go for a block heel if you feel inclined to dress up. 


Fall/ Winter Date Outfit Ideas 

It’s time to get cozy. Fall or winter first dates are one of the best times to bundle and layer up for whatever comes next. There’s something so romantic about the changing of the seasons and about a lot of the fashion that emerges around this time. This is also a perfect opportunity to accessorize for warmth and fashion.

Here are three of my top picks for fall or winter date outfit ideas: 

The Holiday Light Gazing Date Outfit

What To Wear on a First Date: 6 Outfit Ideas


A great and easy first date to prepare for is just simply going and looking at all the pretty festive lights — it’s one of the many classic holiday dates. You can either make it part of a coffee date or grab a casual dinner afterward if you are having a good time. 

Whether you’re walking around or driving, it’s important to stay warm from the elements. Layering is your best friend in the colder months; you can do a lot fashionably to stay warm.

For this date, try a fuzzy coat, tights, and some of your favorite booties to complete the look. And yes, even though it’s wintertime, you should totally still rock a skirt.

 If it’s really chilly, you can never go wrong with a merino wool hat. Bonus points if you can match it to your coat! 

The Movie Night Date Outfit

The ultimate chance to be cozy and cute is easily a movie night. Whether you are out to the theaters or on an easy date night at home, this is the perfect chance to wear something to cuddle up in. Matching loungewear or even matching pajama sets are always welcome!

Pajamas are the ultimate chill ensemble and can help make a date feel more casual. You may not need to accessorize too much with this look since the goal is to be comfy and relaxed.

Another flawless option is a pair of sleek biker shorts and a favorite oversized sweatshirt. It’s chic and low effort so that you can enjoy your time in comfort and style. 

The Pumpkin Patch Date Outfit

What To Wear on a First Date: 6 Outfit Ideas

There is no better fall first date than a good old-fashioned pumpkin patch. Yummy food, a slight chill in the air, and just plain fun. For a pumpkin patch date, you probably want to leave the high heels and dry-clean only blazer at home. 

Instead, opt for a classic pair of jeans, a chunky woven turtleneck sweater with brown or black suede boots.

Some subtle jewelry like gold hoops or pearls can be the right finishing touch. If you still need a little something else to add, a hat or beanie can help complete this look as well. Stay warm with a leather jacket — autumn daytime dates can prove just chilly as winter dinner dates. 

Should I Accessorize for a First Date? 

In my humble opinion, accessories are the secret ingredient for a first-date look. Looking to add some styles to your closet?

Consider jewelry items like a nice solid pair of statement earrings, necklaces, rings, etc. These pieces can work with a casual dinner or a black-tie gala. 

It’s better to have one or two quality accessory items than a bunch of cheap, unsustainable ones. Check out this statement jewelry for more accessory inspo to add to your date night outfits for all seasons and activities.

Functional Fashionista: First Date Outfit Ideas

No matter where your date or life may take you, it’s important to look and feel your best, especially on a first date. Nerves and excitement may be high, so it’s crucial to wear something that lets the real you shine through, no matter what. Whether it’s exploring the city in the sun or sipping tea up by the fireplace, an outfit can really help you feel confident on your next date.

Whether you love wearing dresses, pants, or a little bit of both… the best part of an outfit is always going to be you. Make sure that you find something that you feel great in — because you are. Happy Dating! 



​​12 fun date ideas for spring | Insider 

35 Winter Date Ideas to Cozy Up to Your Significant Other In 2022 | Brides 

7 Fall Date Ideas That Put The "Spicy" In Pumpkin Spice | Elite Daily

Unique Holiday Date Ideas in California | California.com

More Posts

Blog posts

Freedome of Movment: How to style a Kimono this Spring Season

Freedome of Movment: How to style a Kimono this Spring Season

Dive into the world of kimono fashion and discover expert tips on how to style this timeless garment for the spring season. Show oriental elegance and grace.
Balance Between Freshness and Style: Wear Jumpsuits this Spring Season

Balance Between Freshness and Style: Wear Jumpsuits this Spring Season

Discover the ultimate fashion guide for spring as we delve into the versatile world of jumpsuits. Elevate your wardrobe with expert tips on styling jumpsuits for every occasion this season.
What to Wear with Oversize Shirts this Spring Season

What to Wear with Oversize Shirts this Spring Season

Discover the art of styling oversize shirts this spring! From casual brunches to chic evenings out. Elevate your look with versatile pairings.