Perfect 'Fit
From classic LBDs to flirty cocktail dresses, get ready to slay.
By Tianna Soto
Choosing the ideal date night outfit can be tough. If you’re anything like me, you scour your closet looking for the perfect thing to wear only to be left with anxious anticipation (and clothes strewn across the bed). As an avid traveler and city-dweller, my minimal, athleisure-centered wardrobe usually works for hanging out with friends and being on the go. But when it’s time to get glam for a romantic night out, not so much. To avoid last-minute shopping (and stress), I eventually discovered the ultimate solution to all of my fashion woes: having a rotation of go-to date night dresses.
I know, I know — dress shopping can be a drag. I’ve scurried around the mall enough times to know that it can feel impossible to lock in a date night ‘fit that looks amazing and feels comfy. When you’re meeting someone for a date, the goal should be to feel confident, fun, and sexy in your own skin no matter what you’re wearing. However, the last thing you want to worry about is a wardrobe malfunction or your dress riding up in odd places while you’re sipping on your spicy marg.
Whether you’re looking for a classic little black dress, flirty cutout silhouette, or a casual, low-key ensemble that’ll hold you down throughout a night of bar-hopping, I’ve got you covered. Here are 25 date night dresses under $40 for your next evening out. I promise you’ll never have to tear your closet apart again.
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Black Date Night Dresses
Whether you’re preparing for date night or not, everyone needs a little black dress in their closet. This one is on sale right now, and reviewers say the material is soft, non-constricting, and perfect for being on the go. You can wear this one to dinner, the bar, or a fun party with your date — and like many LBDs, it’s versatile enough for everyday wear, too. According to Amazon, this dress fits on the looser side, so be sure to use their sizing chart before ordering to ensure you’ll be comfy all night.
Amazon Rating: 4/5
Available Sizes: S-2XL
If you’re looking for a mid-length dress with a flowy appearance and a bit of sex appeal, this black cami dress might be a great one for you. The dramatic V-neck and open-back design make this a sultry look for your next date night and the multiple sizing options help ensure that you’ll find the comfiest fit for you. Reviewers say they’ve received “nothing but compliments” on the dress and that they “feel beautiful” in it — which is exactly how you should feel on date night, amirite?
Amazon Rating: 4/5
Available Sizes: L Plus-3XL Plus
As someone with a larger bust, I normally steer clear of any dress containing the words “spaghetti straps.” However, after reading the rave reviews on this LBD, I think I’m sold! The flared cami slip dress has been described as “silky soft” and according to one reviewer, the product photos “don’t do it justice.” I appreciate that you can dress it up with some elegant jewelry and heels or down with a leather jacket and sneakers. The next time you’re prepping for date night, having this dress in your closet will spare you the decision fatigue and ensure you’ll be comfy and confident all night long.
Amazon Rating: 4.5/5
Available Sizes: XS-2XL
It’s been a long time since I went out to a nightclub, but if I wanted a semi-daring dress to feel hot dancing in, this would be it. This one from ROSIANNA features see-through sleeves with sexy mesh cutouts on the sides. I love that the brand is all about encouraging you to show off your curves with spicy yet comfortable looks. More of this, please!
Amazon Rating: 4/5
Available Sizes: L-4XL
I love a date night look that feels naturally sexy without being too revealing, and this off-the-shoulder dress achieves exactly that! It’s cute and flirty but still sophisticated, and you can easily pair it with your favorite heels and clutch purse for an elevated look. For a more casual date night, you can also dress it down with leather booties and accessories. Plus, if you aren’t in the mood for an LBD, there are over a dozen colors and designs to choose from.
Amazon Rating: 4/5
Available Sizes: S-3XL
If a soft, slinky evening look is more your style, you’ll love this fun dress for your next date night. The sexy satin material and runched design will hug your curves perfectly while the cowl neck adds a flirty touch. Pair this dress with some statement earrings and your favorite shoes and you’ll be sure to stand out from the crowd.
Amazon Rating: 4/5
Available Sizes: XS-XL
Getting ready for date night and have absolutely no idea what to wear? This sophisticated dress will be perfect for your next evening on the town. The silky fabric, delicate spaghetti straps, and chic midi length will make you ooze cool-girl appeal the minute you enter a room, and you can choose between a variety of stylish colors, including the gorgeous champagne shade above. With over 13,000 reviews on Amazon, the dress is apparently easy to love — customers rave about how beautiful it is.
Amazon Rating: 4/5
Available Sizes: XS-XL
When in doubt, embrace your wild side and rock an animal print to make an extra bold statement. This bodycon dress is an amazing option for a night on the town with your date, and has over 5,000 reviews on Amazon, which makes me believe they’re onto something! The dainty spaghetti straps, curved neckline, and soft fabric are an A+ combination for feeling sexy all night long. And if leopard print doesn’t speak to you, the dress also comes in blue, lime green, and tie-dye, among others.
Amazon Rating: 4/5
Available Sizes: XS-3XL
There’s something about a body-hugging maxidress that feels both sexy and sophisticated. This one is easy to dress up or down with heels and accessories, and I love that it’s long enough to fit a variety of seasons and temperatures. Not only is this classic date night dress super affordable, but it also comes in colors like black, white, royal blue, red, orange, and neon green.
Amazon Rating: 4/5
Available Sizes: S-XL
Casual Date Night Dresses
No matter what your date night has in store, this comfy t-shirt dress will last through it all. There’s something simple yet sexy about a casual look like this, especially the little knot that reveals some leg in a subtle way. This dress has over 8,000 rave reviews on Amazon and comes in a variety of colors and patterns, from blue, purple, and grey to bold florals, tie-dye, and even a dreamcatcher-inspired print.
Amazon Rating: 4.5/5
Available Sizes: S-2XL
If you’re looking for a flowy dress that feels flirty yet casual, you’ll love this one from Amazon. The dress has over 17,000 ratings by reviewers who rave about its versatility and cute design — some customers even bought the dress in multiple colors after realizing how much they loved it. This dress is classy and elegant yet super comfortable — aka perfect for your next date night.
Amazon Rating: 4.5/5
Available Sizes: S-XL
Even if you have pre-date jitters, make yourself feel more comfortable with a casual, loose-fitting dress that’ll flow with you wherever you go. With a relaxed off-the-shoulder design and a soft cotton-polyester fabric, this t-shirt will make you feel cozy and confident. With over 10,000 reviews, this dress is sure to be a staple in your closet. Oh, and the dress runs big, so Amazon recommends sizing down.
Amazon Rating: 4/5
Available Sizes: XS-2XL
This is one of the cutest dresses I’ve seen on Amazon lately, and TBH, I’ve already added it to my shopping cart. With over 42,000 reviews on Amazon, customers rave about the dress and how well it worked for their special events — from bridal showers to Hawaiian luaus and more. Who’s to say it’s not perfect for date night, too? The look can work for spring, summer, or fall, and can be easily paired with a jacket or coat when it gets chilly outside. In my opinion, the dress is a great mix of casual and polished, and if green isn’t your fave, you can choose from black, blue, navy, white, bright orange, hot pink, and more.
Amazon Rating: 4/5
Available Sizes: XS-3XL
If you’re looking for a dress that’s equally cute and cozy for your next date night, you’ll love this one from Amazon. The color is super pretty (and suitable for just about any season!) and the adorable lantern sleeves and belt add a unique touch. Pair it with knee-high boots for a 70s-inspired look or grab booties for a style that screams “cool girl.”
Amazon Rating: 4/5
Available Sizes: S-XL
Flirty Date Night Dresses
The next time you’re trying to figure out what to wear on date night, grab this party dress from your closet and you’ll be good to go! The chic design, cinched waist, and lined top create a semi-structured look that’ll hug your curves and feel comfy all night long. Apart from the color above, the dress comes in wine red, pink, navy blue, and other beautiful shades.
Amazon Rating: 4.5/5
Available Sizes: S-XL
This dress is the perfect mix of playful and sexy with its flowy fabric and elegant v-neck. Whether you’re hitting up happy hour or prepping for a night of dancing, you’ll love this cute, versatile date night look. If light pink isn’t your cup of tea, you can also choose from a variety of colors like green, light blue, white, or army green.
Amazon Rating: 4/5
Available Sizes: XS-2XL
This adorable off-the-shoulder dress is ideal for any cocktail hour, party, or swanky night out with your date. Not only does the stretchy material provide great coverage, but the elegant neckline and high-low design create a memorable silhouette that’ll be sure to make heads turn. In addition to this gorgeous burgundy color, the dress also comes in purple, pink, yellow, blue, classic black, and more.
Amazon Rating: 4.5/5
Available Sizes: XS-2XL
I’m a sucker for any outfit that involves a subtle boho aesthetic, and I especially love rocking the look on date night. If you’re ready to do the same, you’ll love this adorable Milumia dress printed with tiny hearts all over. The flared ruffle sleeves give the dress just the right amount of personality, and you can choose between red, blue, green, gold, violet, or classic black and white. TBH, I may need to buy multiple.
Amazon Rating: 4/5
Available Sizes: L Plus-4XL Plus
With almost 3,000 reviews on Amazon, this dress is a great choice for your next date night. The open neckline and wrap design are sexy in a subtle way, and customers are obsessed with the high-quality material, cozy fit, and how versatile it is to wear year-round. In addition to this pretty purple color, you can also buy the dress in aqua, olive, camel, and many other striking shades.
Amazon Rating: 4.5/5
Available Sizes: S-XL
If you don’t feel like rocking a teeny-tiny bodycon and aren’t in the mood for a maxi, you’ll find a middle ground with this adorable knee-length dress. Customers describe it as “cute,” “fun,” and “effortless to wear,” which sounds like an A+ date night outfit to me. According to Amazon, the material isn’t super stretchy, so be sure to check the size chart before ordering your own dress to make sure it fits just right.
Amazon Rating: 4/5
Available Sizes: XL-5XL
With over 3,000 reviews on Amazon, this date night dress is a winner. The off-the-shoulder design is ideal for when you want to show a little skin without being too revealing, and the breathable fabric means you’ll stay comfy in a crowded bar. It’s casual enough for a walk around town but sophisticated enough to make a major impression. Plus, you can choose between black, turquoise, yellow, or statement-making red.
Amazon Rating: 4/5
Available Sizes: L-4XL
Flowy Maxi Dresses
This gorgeous dress has over 8,000 rave reviews on Amazon, and it’s easy to see why. With delicate fabric and a flowy design, the dress is soft, romantic, and perfect for your next evening out. Whether you’re meeting your date for a fancy dinner or heading out for cocktails, this dress will make you feel elegant in every way.
Amazon Rating: 4/5
If you’re like me and want to keep your outfit simple and classy on date night, you’ll love this loose-fitting maxi dress that can be easily dressed up or down. It comes in a variety of colors and prints, you can choose between spaghetti straps or sleeveless, and the dress has pockets, which is obviously the cherry on top. Some reviewers say it’s the “best Amazon purchase” they’ve ever made, so make of that what you will.
Amazon Rating: 4/5
Available Sizes: S-3XL
When shopping for your go-to date night dress, it’s important to find something versatile, fun, and comfy. This flowy dress is a great choice and works for a variety of settings, from bougie happy hour to a romantic night on the beach. The sensual V-neck, loose-fitting sleeves, and ruffled hem remind me of summers in Spain, and you can choose between a bunch of different colors depending on the style you’re going for.
Amazon Rating: 4/5
Available Sizes: XS-2XL
Personally, my main requirement for a go-to date night dress is that it needs to be comfortable — full stop. You deserve to feel cozy and confident in your outfit no matter where the evening takes you, and this fun maxi dress from Amazon is sure to do the trick. It comes in over a dozen patterns and a range of size options, and customers love how soft and versatile the dress is. Time to add it to your cart ASAP!
Amazon Rating: 4.5/5
Available Sizes: 1X-4X
I know how stressful it can be to choose an outfit for date night, but don’t worry — these options are sure to hold you down in the moments you need it the most. Whether you prefer a maxi, midi, bodycon fit, or a teeny-tiny black dress you can wear for every occasion, these date night dresses under $40 will be staples in your closet soon enough.
FAQs
What do you wear to a date night 2022? ›
On a first date in 2022, it's best to aim for a simple, yet elegant outfit. 2022 is all about timeless neutrals so go with jeans, heeled ankle boots, neutral tops, and uncomplicated pieces. You're already nervous enough on a first date, you don't want to be overthinking everything you're wearing.
What should I wear on the first day of spring 2022? ›This spring, go for the essentials. Clothes and outfits such as suits, shirts, tailored pants, you can never go wrong with. Top up your classic style with modern accessories that make a statement and you would have modern clothing in no time.
What should I wear to my friends Dinner 2022? ›- Chic Dresses.
- Jumpsuits.
- Button Down Shirt + Pants/Jeans.
- Feminine Blouse + Jeans.
- Blazer + Pants.
- Cute Top + Midi Skirt.
- Leather Jackets.
- Long Coat + Pants / Skirt.
A turtleneck-blazer combination is a classic, so pairing the pieces with leather pants and boots keeps the look feeling special. Although you may need to add a coat, the pairing of a sweater and leather skirt is one perfect outfit. Not only is a tailored suit classic, but it's also ultra-comfortable.
What do you wear on a date night? ›- A Pretty Top and Jeans.
- A Matching Top and Skirt Set.
- Leather Pants and a One-Shoulder Top.
- A Frilly Dress and Sneakers.
- A Cropped Blouse and Shorts.
- A Bodysuit and Printed Pants.
- Wear Something That Makes You Feel Confident.
- When in Doubt, Wear Red or Black.
- Avoid Wearing Orange and Brown.
- Wear Something Comfortable and Practical.
- Show Off Your Neck Instead of Your Chest.
A pretty top and jeans are foolproof, whether you're wearing flats or a trendy kitten heel. In the colder months, you can't fail in a sweater dress and pretty jewelry. For a casual meet-up with friends or family, you can totally embrace laid-back pieces like a cozy sweater, loose-fitting jumpsuit, or sneakers.
How do you dress for a fancy dinner? ›Athletic shoes, flip-flops, shorts and T-shirts are not appropriate. Casual elegant: Elevate your look from a working professional to a more dressed-up dinner guest. For him, this could mean a dark suit or button-down with a sportcoat. For her, a more formal black dress or pantsuit would be perfect.
How do you look classy in the winter? ›- START WITH THERMAL BASICS. If you want to look stylish and warm, then the quickest way to get there is to buy a pair of wool or thermal tights that you can wear underneath your jeans and pants. ...
- PICK THE RIGHT WINTER JACKET. ...
- PROTECT YOUR SHOES WITH WATER REPELLENT.
You can't go wrong in a dress! Wear your dress at or above the knee and accessorize it with some flirty shoes and jewelry. Choose a fitted but not skin-tight dress. A wrap dress is very feminine and sexy and will minimize your midsection.
What are the spring 2022 colors? ›
Spring 2022 Color Trends
Yellow, pink, and green dominated many of the collections. Often used as a striking solid, these bold colors sometimes accented a neutral but often were used alone for a bright blast of fun color. Aqua, royal blue, and beautiful reds round out a full and vibrant spectrum.
I know, I know—animal prints aren't exactly anything new, but this trend is timeless and ever-evolving. For 2022, we're trading in leopard and snakeskin for zebra and tiger prints, and keeping an eye out for abstract versions that create a cool twist on the classics.
How do you dress elegantly in spring? ›Elegant Outfit Ideas for Spring 2022 - YouTube
What should a 50 year old woman wear on a first date? ›Don't look like you're trying too hard
Dressing them up or down is easy. A silk blouse or a V-neck sweater with low heels or pointy flats looks feminine and polished; a simple white T-shirt or crisp white shirt with sleeves turned up and rolled with leather ankle boots looks classy and classic.
You don't want to give off the impression that you're frumpy or sloppy. Avoid any clothing materials with holes, stains, or pilling. Your first impression should be neat, clean and borderline professional. That's a really difficult look to pull off in tattered clothes, even if they are old favorites!
How do you look good before a date? ›- Get glowing skin. ...
- Play feel-good music. ...
- Attend a Power Workout class. ...
- Drink vitality. ...
- Make your eyes pop. ...
- De-bloat and de-stress. ...
- Smell amazing. ...
- Use a highlighter under your eyes and on your bottom lip.
According to the study, the most attractive color in terms of fashion is black. The second most attractive color is pink, followed by the color yellow.
How long should a first date last? ›What we'd like to do is give you a starting range and then we'll give you a few questions to ask to adjust that appropriately. Then, with that length in mind, you can start to plan your date activities. The usual length of a first date is between 45 minutes to 2 hours, with an average length of about one hour.
What should I wear on a date at 40? ›What to Wear on FIRST DATE (Divorced, Over 40, Style Tips and ...
What should I wear on date night with my husband? ›- White Blazer + Black Leather Shorts. ...
- Boyfriend Jeans + Crop Top + Heels. ...
- Denim Jacket + Midi Skirt. ...
- Jumpsuit + Clutch. ...
- Off-The-Shoulder Top + Cropped Denim. ...
- Statement Top + Skinnies + Bright Sandals. ...
- All Black Everything. ...
- Peasant Blouse + Denim Skirt.
How should I dress for a date at home? ›
Pair flirty shirts with your most comfortable jeans and skirts for your virtual date night in. It's all about blouses with exciting details like asymmetrical necklines, one-shoulder, wrap and peplum styles in bright colors. Want something a bit more classic? Opt in to date night colors like black, red and lavender.
What is elegant dress code? ›It means the ladies can wear sexy backless or shoulderless cocktail dresses (not long gowns) and the guys should at least not wear hoodies and running shoes.
What is classy casual dress code? ›Dressing classy but casual is all about combining high-quality clothes for a stylish look. You can look classy with clean jeans and a nice, well-fitting top. Or, pair slacks with a dress shirt for a business casual look. During summer, wear shorts with a loose-fitting t-shirt.
What is casual elegant dress code? ›Elegant casual is also known as “ casual elegance” and is typically similar to something you would wear to a country club or upscale restaurant. A step above resort evening, with this dress code, men are expected to wear a long-sleeve dress shirt with slacks and dress shoes—no shorts, t-shirts, or sandals.
What should a 50 year old woman wear on a first date? ›Don't look like you're trying too hard
Dressing them up or down is easy. A silk blouse or a V-neck sweater with low heels or pointy flats looks feminine and polished; a simple white T-shirt or crisp white shirt with sleeves turned up and rolled with leather ankle boots looks classy and classic.
For women, go with a little black dress or a casual blouse and jeans finished with feminine accessories and a natural makeup look. Stick to solid colors or small-scale prints and avoid anything with loud patterns and obnoxious colors that may distract your date.
What should a woman wear on a dinner date? ›A pretty top and jeans are foolproof, whether you're wearing flats or a trendy kitten heel. In the colder months, you can't fail in a sweater dress and pretty jewelry. For a casual meet-up with friends or family, you can totally embrace laid-back pieces like a cozy sweater, loose-fitting jumpsuit, or sneakers.
What do you wear on a date summer 2022? ›For the first date, you should wear something cool, but classy, but cool – like a white muscle tee with pink high waisted pants and heels. High-waisted pants will enhance your figure and make you look super tall, while the muscle tee will make you look cool. And high heel sandals will prove you can walk in heels.
What do guys expect on first date? ›Good men want the same things good women do—genuine sincerity, trustworthiness and confidence. If you connect with someone, follow it up with a second date, who knows where it may take you.
What should a 60 year old wear on a first date? ›Classic is always classy. A good starting point when dressing for a first date is to find a happy medium between casual and classy. A great way to do that is by using classic fashion staples. If it's fashion for a 50-year-old woman or man, the same rules can apply.
How can I look stylish at 50? ›
- Get a good tailor. ...
- Define your waist, no matter how big or small.
- Keep your skirt and dress lengths to the knee.
- Don't show too much skin: too-short skirts and tops that are too low don't flatter anyone.
- Keep it simple; stay away from bling.
- Mute the loud prints, lean toward solids.
Studies reveal that red is the most attractive colour to both men and women but, curiously, the two genders are attracted to the same colour for different reasons.
What is the most attractive color for a girl to wear? ›According to the study, the most attractive color in terms of fashion is black. The second most attractive color is pink, followed by the color yellow.
What should I wear on a date at 40? ›What to Wear on FIRST DATE (Divorced, Over 40, Style Tips and ...
What should you not wear on a first date? ›You don't want to give off the impression that you're frumpy or sloppy. Avoid any clothing materials with holes, stains, or pilling. Your first impression should be neat, clean and borderline professional. That's a really difficult look to pull off in tattered clothes, even if they are old favorites!
How long should a first date last? ›What we'd like to do is give you a starting range and then we'll give you a few questions to ask to adjust that appropriately. Then, with that length in mind, you can start to plan your date activities. The usual length of a first date is between 45 minutes to 2 hours, with an average length of about one hour.
What do you wear on a summer date? ›- Halter Top + Distressed Jeans + Gold Jewelry. ...
- Babydoll Dress + Platform Sandals. ...
- Backless Bodysuit + White Jeans + Straw Hat. ...
- Red Two-Piece Midi Dress + White High Heel Slide Sandals. ...
- Floral Print Jumpsuit + Heeled Sandals + Pendant Necklace. ...
- Green Halter Top + White Denim + Platform Sandals.
Fun sneakers or booties, jeans and a graphic tee with a jacket are perfect. I also love a good chunky sweater and high waisted jeans with booties. For the summer, choose a flowy summer dress and a sandal. A denim skirt and sandals with a tank is also great.
What do you wear on a date night at home? ›Pair flirty shirts with your most comfortable jeans and skirts for your virtual date night in. It's all about blouses with exciting details like asymmetrical necklines, one-shoulder, wrap and peplum styles in bright colors. Want something a bit more classic? Opt in to date night colors like black, red and lavender.