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5 Best First Date Outfit Ideas

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First dates should be easy — in theory. We’re just meeting someone to see if we click. We’re looking for elements of chemistry and compatibility. If those don’t exist, no harm, no foul, right?

But that’s not how dating works. We’re all sensitive to rejection. We’re nervous about meeting new people — rightfully so for women whose risks on a first date are far higher than a man’s when our physical safety cannot be guaranteed.

There’s plenty to worry about, and many precautions that we can, and do, take prior to that first date from light social media stalking to telling friends and family where we’ll be and when we expect to be home. 

The Best First Date Outfit Ideas

With all the anxiety around first dates, what to wear shouldn’t be that big of a deal. Yet, it is. It creates that first in-person impression, and we want to feel good about how we look.

We want the other person to like how we look, too. Let’s take the stress out of first date outfits by talking about some of the best , classiest and simplest ones to go with for that first true introduction.

Outfit 1: Jumpsuit with Wedge Sandals, Purse, and Cardigan

Jumpsuit with Wedge Sandals, Purse, and Cardigan
Outfit via Stitchfix

Many first dates start with a drink. That might be coffee or cocktails. A jumpsuit is versatile. We can dress it up for a fancier location or dress it down if we want to appear more casual. 

Our main concern for the first date should be combining comfort with style. We want to look good but feel good, too. While jumpsuits can be uncomfortable when we have to strip completely down to use the restroom, they have the benefit of being comfortable, flattering, and stylish, too.

Pair it with a statement purse and a cardigan or jacket. If we want to convey a more professional look, we can add a blazer.

For a casual but cool vibe, add a leather (or faux leather) or jean jacket. If we want a more bohemian look, we can add dangly earrings and a kimono. Pair with wedge sandals, and we’re all set for a first date delight (or disaster)!

Outfit 2: Halter Top with Trousers, Hoops, and Flats

Outfit 2: Halter Top with Trousers, Hoops, and Flats
Outfit via Stitchfix

This next outfit choice can be easily customized for individual comfort. A halter top with trousers, hoops, and flats is a simple but chic choice. In the winter, we can swap the halter top for a sweater.

We can easily swap out the trousers for jeans if that’s more comfortable or pair it with a skirt or shorts. These items are perfect for a capsule wardrobe because they can mix and match to create many different looks.

It’s casual, comfortable, and — yes — hot! The flats are a great choice for comfort during a first date. We really don’t need to overthink this (more than we already are).

Simply pairing a favorite shirt with a favorite pair of pants and dressing it up with jewelry should be plenty. They’ll like us or they won’t, but we should feel good about what we’re wearing because confidence is key. 

Outfit 3: Midi Dress, Wedge Sandals, and Bracelets

Outfit via Stitchfix

Another great first date outfit is the sun dress! Combine this midi dress with some wedge sandals for a casual but sexy vibe. We can add a jacket or cardigan, dress it up with jewelry, and make a strong and flattering first impression. 

Any sun dress will do, but a midi, wrap, or shift dress can all be flattering depending on our body type and comfort.

Pair with bracelets and earrings, and we’re ready. It shows that we made an effort for the date without going overboard or being too formal for the occasion. 

Outfit 4: Body Suit, Ripped Jeans, and Sandals

Outfit via Stitchfix

I never thought I would be a person to rock a bodysuit. I am short and curvy and conscious of looking like a dumpling depending on what I’m wearing. I wasn’t sure this look would be flattering. And then I tried on my first long-sleeved black bodysuit and paired it with jeans. Holy wow!

Yes, I’ve got some curves, but this look seems universally flattering. Just pair it with a favorite pair of ripped jeans for that casual look and find a comfortable but cute pair of sandals to go with it. Or boots for an added kick of confidence.

It’s another versatile look that we can customize to suit our personal style. My closet looks like I have several personalities, but I tend to mood shop.

Depending on my vibe for a first date, I might want to throw on a boho kimono-style cardigan and dangly earrings to create a particular look with this, or I might pair it with a blazer and statement necklace.

How we give it that extra flair doesn’t matter nearly as much as how good about ourselves we feel when we’re done. 

Outfit 5: The Little Black Dress (LBD)

Outfit via Stitchfix

The little black dress is a classic for a reason. It can be dressed up or down. It works for weddings or funerals. There’s nowhere the little black dress can’t go and manage to look AH-mazing!

It’s definitely a great option for a first date, and I have to say that I love these particular wedge sandals and now desperately want a pair!

We can take the LBD out to coffee or for cocktails and still manage to convey a casual, first date appeal. The color is universally appealing, and if we want to shake things up, we can add a pop of color with our accessories.

For instance, I have a LBD that I like to dress up with a mustard yellow cardigan and matching shoes, or I’ll skip the cardi and add my bright red ballet flats and a favorite pair of earrings. 

classy beautiful woman with a little black dress, park in the background
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Bonus: Outfits to Avoid

In truth, there are a few outfits we might want to avoid for a first date. I’ll give a couple of examples to illustrate the point. Maybe consider shelving these for another time (or never, depending). 

Outfit 1: Loungewear

Outfit via Stitchfix

Not all loungewear is created equal. Some items sold as loungewear look like pajamas, and no amount of dressing them up will magically transform them into a date-worthy outfit.

Trust me: If your loungewear doesn’t truly pass as regular clothes, you will feel uncomfortable the whole time you’re wearing it, which will be reflected in how you interact on your date. Just say no to loungewear and opt for an outfit you don’t regularly sleep in — at least for the first date.

Unless we’ve agreed upon a breakfast date where the theme is pajama-casual, loungewear is probably not the right choice.

Although, I did once have a first date at a gym, which definitely sounds weird but was really enjoyable. In that case, loungewear or activewear works and is appropriate to the activity.

If you really feel strongly about wearing loungewear out, ask a friend if it looks like you rolled out of bed in your pajamas or if your loungewear can pass for casual outdoor wear, too. 

Outfit 2: Tight-Fitting Clothes and High Heels

Outfit via Stitchfix

If you feel sexy in tight-fitting clothes, go for it. But don’t wear that dress you know you’re going to be tugging into place the entire date.

Confidence matters, so the most important thing you can do is pick out an outfit you feel good in. Trust me: If you feel good, you’ll look good, too.

The outfit above is sexy, but nothing is sexy about tugging clothes up or down self-consciously or wobbling in high heels. 

And girl, you cannot run in those shoes. Even if you’re one of those magical people who can, it’s not the safest footwear until you’ve verified whether you’re meeting up with Prince Charming or Hannibal Lecter.

Skip the heels that’ll hurt your feet and opt for more comfortable shoes. It’ll help you focus on your date and whether or not they pass the vibe check rather than your poor hurting feet.

Plus, if you need to make a quick escape, you’ll certainly be faster in other shoes. 

Once again, if you feel sexy and comfortable in your heels, wear them. All first date decisions need to pass our own vibe check first. If it feels good to us, that’s what matters.

After all, if the first date completely fizzles, we can always make the most of the evening by meeting up with friends or enjoying our drink on our own while looking hot doing it. 

First Date Potential

If a first date is magical, it won’t really matter what we wear.

For example, I can’t even remember what I was wearing that one time my date melted down over margaritas and interrogated me over my bathroom habits, but I absolutely remember what I was wearing that time I met a handsome man for coffee and had a wonderful time getting to know him better.

Dates can go either way, and all we can do is try to make an effort to look our best and make a good first impression — or better, an honest one. 

Throw out all the fashion rules. Wear what makes you smile. If it doesn’t make your date smile, maybe they just aren’t the one for you.

The above outfits are from StitchFix because I love how they combine and customize styles to fit the individual. However, these same ideas can easily be cobbled together from your favorite department store or even local thrift store.

It’s not about the price tag but about the look and feel of an outfit. The best outfits should convey a little of your personality while making you feel wonderful. 

The Truly Charming