Outfits to Wear on Dates

First dates can be both exhilarating and nerve-wracking at the same time, making a stunning wardrobe even more crucial to feeling as confident as possible. Staples that make you feel your best are a great place to start when creating an outfit, whether it be a T-shirt and jeans, a stunning dress, a matching set, or a jumpsuit. Be it a shirt with a unique cut, jeans with a striking design, vibrant heels, or statement earrings, eye-catching clothing and fun accessories will attract your date’s attention and definitely make a wonderful impression, too.

You can definitely get away with wearing casual clothing, if that’s your style, depending on the date. A pair of pink kitten heels also looks wonderful as a focal point with a T-shirt and jeans, just as white sneakers are the ideal counterpoint to a feminine dress. Speaking of jeans, they are unquestionably appropriate for a first date. For a polished casual look, try a lovely top and colorful mules with straight-leg vintage-washed pants. Alternatively, balance out a billowing crop top with a long pair of cut-off shorts or loose-fitting bottoms.

Guys, we’ve all been there. You’re on a date, and you get one look in your rearview mirror, and you start to feel like a deer caught in headlights. Fortunately, there are lots of outfit options out there! We have a look at some of our favorite outfits that work well with the beach setting and get you ready to go on a date with confidence.Guys like to see a woman who takes care of herself, so make sure you get your hair, skin, and nails looking healthy. Take a few minutes each night to exfoliate and shave your legs, so they look their best in a black dress or skirt. When it comes to nails, I’ve found that clear acrylics are really easy to remove with acetone. Also keep in mind that most fabrics don’t like sweating excessively — be sure to wash them the day before you need them!

Outfits to Wear on Dates

If current trends are the way to your heart, channel that energy on a first date. A bustier-inspired top will read fashion-forward and fresh, as will a pretty puff sleeve. Here for all things ’90s? Anchor your look with sleek leather pants, a minimalist heel, or both. Whatever your taste, keep scrolling for 10 stylish first-date outfits that work for coffee, drinks, dinner, and beyond.

A Pretty Top and Jeans

outfit 1
DESIGN TIANA CRISPINO

If jeans are your comfort zone, dress up your favorite pair with a pretty puff-sleeve top and colorful mules. Great for a picnic or a low-key night on the town, this first date outfit exudes effortless confidence.

A Matching Top and Skirt Set

outfit 2
DESIGN TIANA CRISPINO

A matching set takes the stress out of outfit planning, and is right on trend in 2021. This ribbed top and skirt go well together for drinks or dinner. Wear them with delicate sandals and a modern mini bag.

Leather Pants and a One-Shoulder Top

Pair these sleek leather pants with an asymmetrical, strapped top for a date night look that is reminiscent of the 1990s. Delicate gold earrings are a sleek finish made even better with dewy makeup.

A Frilly Dress and Sneakers

A frilled dress reads feminine but not overly sweet when paired with white canvas sneakers for a daytime date or relaxed meet-up. A polished gold anklet is a chic and unexpected addition to your easygoing first date outfit. It shows that you put thought into it.

A Cropped Blouse and Shorts

Balance out the boldness of a billowing crop top with a pair of long shorts and lace-up sandals.

A Bodysuit and Printed Pants

outfit 6
DESIGN TIANA CRISPINO

You can’t beat a bodysuit for an effortlessly stylish date night outfit—team yours with zebra-print pants and a gold pendant necklace for guaranteed impact.

A Bustier Top and Slip Skirt

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DESIGN TIANA CRISPINO

A slip skirt is fail-safe for any date. Pair yours with a bustier top and lace-up espadrilles for a low-key, summery vibe.

A T-Shirt and Jeans

outfit 8
DESIGN TIANA CRISPINO

Despite being go-to staples, a T-shirt and jeans are anything but boring when modern details like padded shoulders and a corseted waist are part of the equation. Pastel kitten heels steer the date night outfit in a dressier direction while maintaining ease.

A Midi Dress and Sandals

Midi dresses exude easy romance, making them ideal for first date outfits. This style, featuring a peekaboo back, reads decidedly fresh in the heat. Play up the midsummer aesthetic with colorful earrings and flat sandals.

A Jumpsuit and Heels

It doesn’t get easier than a jumpsuit when dressing for a date in a hurry. To make things easier, stick to a timeless neutral palette—you’ll look relaxed yet elevated for dinner or drinks.

You only get one chance to make a first impression. Perhaps you’ve been out of the dating game for a while and are heading off on your first date in a long time. Or maybe you’re going out for a long-awaited date with your significant other. Either way, you’ll find plenty of inspiration in this article on how to dress on first date.

What to Wear on a Casual First Date Female?

First what should you consider when putting together your first date outfit?

#1 Wear What You’re Comfortable In

How to dress for a first date - Abi in a jumpsuit | 40plusstyle.com

While you’ll want to choose something special, you’ll want to make sure you feel comfortable. You don’t want to be fidgeting with a neckline or feeling that your waist is digging in.

#2 Stay True To Your Style Personality

Not only do you want to be comfortable, you’ll also want to express yourself as you really are. After all, you’ll want to the other person to like you for YOU. Stay true to your unique style personality.

So if natural is normally your style personality, stay true to that and just glam it up a bit.

Of course it’s perfectly fine to show up as the best version of you or the most sexy version of you, but stay true to yourself.

#3 Add An On Trend Piece

You want to look current on your first date. Even if your style is classic. In that case, make sure your classic style is current. Adding just one new item to your outfit can make all the difference.

#4 Mix And Match Formal And Casual

Patricia in a skirt and denim jacket | 40plusstyle.com

To look great yet as if you haven’t tried too hard, mixing formal and casual pieces is a good formula.

#5 Think About Where The Date Is

For example, if you’re having dinner, you’ll want to concentrate on your top half. But if you’re having a picnic, you’ll want to make sure you can sit down comfortably.

#6 Wear Tactile Fabrics

If you want to give your outfit a romantic feel, then wearing tactile fabrics like silk, satin or leather is perfect.

#7 Show Off Whatever You’re Most Confident About

What to wear on a first date - Nikki in a black dress | 40plusstyle.com

If there’s anytime you want to feel confident, it’s on a date. So, if you want to add some subtle sex appeal to your outfit, think about showing off the area of your body you like the most, whether that’s your shoulders, your legs or your decolletage.

How To Dress For A First Date A First Date

Now, let’s look at how to dress for a first date and some specific outfits you could put together. You’ll find a first date outfit capsule at the end so you can look at how you can mix and match all the different clothes, shoes and accessories.

Dresses And Skirts Are Perfect For First Dates

What to wear on a first date to feel confident and look amazing | 40plusstyle.com

Dresses or skirts would be a natural choice if you want to create an impact. 

A red dress is ideal if you want to create a big impression, and a little black dress will, of course, always be appropriate.

Skirts and dresses for a dinner date | 40plusstyle.com

Fraiche by J Wrap Front Long Sleeve Dress – Kay Unger Raven Draped Sheath Midi Dress – Ted Baker London Kiylie Floral Satin Asymmetric Skirt – Careste Georgia Silk Skirt

Shoes For A First Date

Karen Millen Compact Stretch Single Breasted Jacket – VICI Collection Satin Halter Neck Blouse – Wit & Wisdom ‘Ab’Solution Itty Bitty Bootcut Jeans – Calvin Klein Beeta Pointy Toe Flat – Reiss Arden Basket Weave Clutch – Open Edit Twisted Link Collar Necklace –

Your shoe choice can make a big difference to the look of your outfit. You could choose a classic option like a pair of pumps or block heel sandals, or opt for an edgier look with a pair of ankle boots or pointed toe flats.

Shoes for a dinner date | 40plusstyle.com

Calvin Klein Beeta Pointy Toe Flat – Cushionaire Alba Block Heel Sandal – Nina 60 Pointy Toe Pump – 27 EDIT Naturalizer Florentine Bootie

Accessories

Karen Millen Compact Stretch Single Breasted Jacket – Kay Unger Raven Draped Sheath Midi Dress – Cushionaire Alba Block Heel Sandal – Chrysansmile Leather Quilted Crossbody Bag – Open Edit Twisted Link Collar Necklace – Jennider Helena Chain Drop Earrings

Choose clutch bags and statement jewelry. If you want to add extra warmth, you can always add a pashmina over your shoulders.

Clutch bags and statement jewelry | 40plusstyle.com

Reiss Arden Basket Weave Clutch – Open Edit Twisted Link Collar Necklace – Jennider Chrysansmile Leather Quilted Crossbody Bag QBSM Helena Chain Drop Earrings Pashmina Wra

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