25 First Date Outfit Ideas

If there’s ever a time when you want to make a great first impression, it would be on a first date. Whether it’s dinner and a movie, dining at a fine restaurant or being someone’s plus one at a wedding or business event, it’s important that you wear something that is truly memorable—something that says “You will not regret one moment that you spent with me.”

So, how do you go about finding that perfect outfit? Consider the occasion. Consider your personal style. And also consider your desired comfortable level. After all, looking good is one thing. But if you can find something that you also feel good in, you’re sure to have a truly amazing time!

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Pretty in pink

Pretty in pink
Pretty in pink/via

Pink is always a nice option because it’s soft and romantic. What’s really great about this particular look is that pink is modernized with the help of some sequins. Plus, there is an element of surprise, thanks to a pair of leopard pumps.

Fashionably casual

Fashionably casual
Fashionably casual/via

If you know that you’re going to the movies, you can showcase so many sides of your personality by going the casual route. A graphic tee, some jeans and a printed blazer will give your date some insight into the person you are.

Wonderful for a wedding

Wonderful for a wedding
Wonderful for a wedding/via

If your first date a wedding? If so, wow your date, the guests and the bridal party with a dress just like this!

From work to drinks

From work to drinks
From work to drinks/via

If you’re a professional who is drawn to guys who have a lot of ambition, scheduling might be hard. But if you wear a flirty top along with some fitted flare pants to work, you can easily meet him for drinks afterwards.

Outdoor concert in boyfriend jeans

Outdoor concert in boyfriend jeans
Outdoor concert in boyfriend jeans/via

Are you both planning to check out one of your favorite bands at a local amphitheatre? What this look proves is that you can be super comfortable and super stylish at the same time. Plus, the boyfriend jeans send a hint that you might be taking applications for one. (The right one!)

Perfect date night dress

Perfect date night dress
Perfect date night dress/via

Looking for a date night dress? If so, this one is super-flattering. The color is easy on the eyes and the cut is very figure flattering. Plus, with the right kind of accessories, you can either dress it up or down.

Versatile jumpsuit

Versatile jumpsuit
Versatile jumpsuit/via

We are totally in love with this jumpsuit! There are so many reasons why, but the main one is virtually any body type can wear it and look unforgettable in it.

Rocker chic

Rocker chic
Rocker chic/via

Are you a rocker at heart? If so, this kind of outfit will convey the message without a ton of overkill. (We love the messy bun and boots!)

Perfect black dress

Perfect black dress
Perfect black dress/via

Every woman needs a little black dress. If you’re in the market for one, this style is perfect. It’s innocent and sensual—a great message to convey on a first date.

Modestly sexy

Modestly sexy
Modestly sexy/via

If you want to look sexy without being too sexy, try this look. The jean leggings will show off your shape while the top and colorful blazer will still keep some secrets concealed.

Sweet in lace and polka dots

Sweet in lace and polka dots
Sweet in lace and polka dots/via

Polka dots make a statement. That’s because whether they are technically in style or not, they send the message that you don’t care. You just love ’em! And individuality is always a plus when making a first impression. Plus, if you add to it some lace, that makes your look super sweet.

A look for all seasons

A look for all seasons
A look for all seasons/via

If you want something that’s casual and eye-catching that you can basically wear any time of the year, this look will meet your needs. Plus, it’s attractive with or without accessories.

Graphic tee and tulle

Graphic tee and tulle
Graphic tee and tulle/via

If you’re going out for dinner and your date informs you that it’s an occasion to dress up, a tulle skirt and graphic tee is a way to look appropriate for the occasion while being youthful and modern too.

Great shorts and sequins for summer

Great shorts and sequins for summer
Great shorts and sequins for summer/via

During the summer, it’s time to dress for the heat. The temperature, yes. Also the potential of where your first date might lead. A pair of shorts along with some sequin items, lets your date know that you’re ready for just about anything!

Feminine in white cotton

Feminine in white cotton
Feminine in white cotton/via

This white cotton dress is effortlessly beautiful. There is really nothing more that needs to be said.

Cute in colored jeans

Cute in colored jeans
Cute in colored jeans/via

If you like the way your body looks in fitted jeans, spice things up a bit by wearing some colored ones instead of denim. If you add to it a pair of pumps, your legs will look long and your backside will look even more appealing.

Short ‘n sweet

Short 'n sweet
Short ‘n sweet/via

We’re not sure what we like more. The color combo or the style of this mini-dress. And what if you’re not comfortable wearing something this short? No worries. Just add some leggings or shorts and you’re (still) good to go.

Camouflage and killer heels

Camouflage and killer heels
Camouflage and killer heels/via

Another great casual look are some drawstring camouflage pants and killer heels. If you add to it a blue jean vest, you will convey “There’s more than meets the eye” and “I have a bit of a wild side” without actually saying a word.

Great no matter where you go

Great no matter where you go
Great no matter where you go/via

A romantic guy may want to surprise you on the first date. With this beaded shirt, solid top and great accessories, you’ll be dressed appropriately no matter where you go.

Movie in a maxi skirt

Movie in a maxi shirt
Movie in a maxi shirt/via

If you’re headed to a movie but you don’t really feel like wearing jeans, substitute it for a maxi shirt. It’s casual, feminine and comfortable. Plus, you can still wear your favorite graphic T-shirt.

Fashion with flare

Fashion with flare
Fashion with flare/via

Flare pants are back. So, if you’re going on a picnic or to a wine tasting, give this look a try. (Don’t forget the hat!)

Twist to a jean shirt

Twist to a jean shirt
Twist to a jean shirt/via

If you absolutely love your denim shirt but you’re going someplace where jeans wouldn’t really fit the bill, a long and colorful pleated skirt will add a new twist it to. Beautifully so.

Rock a Fedora

Rock a Fedora
Rock a Fedora/via

Yep. One accessory can go a really look way. Take this Fedora, for example. It’s super stylish. Especially on those days when you can’t seem to get your hair to look quite right.

An updated way to wear a pencil skirt

An updated way to wear a pencil skirt
An updated way to wear a pencil skirt/via

If you love your pencil skirt, but you’d rather not look too dressy, let this look serve as some inspiration. A fitted tank and your jean jacket will give it an updated feel.

Warm in winter

Warm in winter
Warm in winter/via

We thought it would be a good idea to mention something for winter. The color combination is perfect for any skin tone and the boots are sexy in their own special way. Enjoy your first date!

1 thought on “25 First Date Outfit Ideas”

  1. Sienna says:

    Great, thank you!

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