6 Date-Night Outfit Templates That Are Supremely Flattering And Gorgeous
We’re getting out of the house. Join us?
by The Candidly Team
Are you like us in this way? Where the idea of getting dressed up to go out sounds tremendously fun in the moment we’re making the reservations, buying the tickets, scheduling the sitter, etc. But when the moment comes to actually do it, we feel pretty much … deflated.
Is that the word?
What even is the word for feeling depleted of energy, devoid of inspiration, icky about our hair and skin, probably some degree of bloated, and like we’d rather be shoved into an ice bucket than pried out of loungewear?
It’s not that we don’t love “dress up” clothes. We really do. Probably too much.
We look forward to an occasion where we can wear them (and look good in them), but putting it all together often winds up feeling like too much of a lift. Or a disappointment.
Even when we do put in the effort, we end up making choices that don’t really work together. The only top that feels good on our stomachs looks weird with the only jeans that don’t look too casual, and it’s all wrong with the shoes we’ve been dying to have an excuse to wear even though they also happen to butcher our feet.
See? Deflating.
All of that said, we weren’t ready to throw in the towel with dressing up, so we decided we need a solution. Which we found in the form of a template. Six of them actually.
We compiled six VERY easy, VERY flattering, VERY specific date night looks that make us feel all the things we want to feel when dolling ourselves up to swirl around town with our partners, (who incidentally will never see this article, because they take all of 22 seconds to get ready, because they’re pretty much always wearing the same. exact. template).
We don’t like to over-promise, but we’re just gonna go ahead and say, you will look excellent in any one of these looks. They’re fun. Foolproof. And they give you just the right amount of wiggle room to make them as sexy as you see fit. You’ll see what we mean.
Get ready to make reservations. Off you go.
1. The LIttLE BLACK DRESS
Skims Long Slip Dress
We start simple. LBDs are infallible. Timeless and gorgeous. One and done. All you have to do is find THE ONE (or the few) that fit and feels exactly right on your body. Some of you will skip over this dress for fear of it being “clingy” and “revealing,” but it’s made by Skims, a brand known for making shape wear for all kinds of curves and in an extended size range. This extremely lovely-feeling, buttery dress, therefore, holds us in and smooths us all over, while making us look long and lithe and as close to 6ft models as we come. We actually wrote a whole unsponsored article about it with many pics HERE. You can throw it on with any piece of outerwear and any comfy shoe and look like you stepped out of Breakfast at Tiffany’s. Our Editor-in-Chief, Audie, is wearing hers above with a jean jacket* and UGGs* for example. And it works.
Price: $80
Quince Washable Stretch Silk High Neck Midi Dress
We’ve seen versions of this perfect, silk LBD from almost every designer this year, but this one from Quince has all the drape and criss cross back and skimming fit in real silk for half the price. Plus, it’s washable, which saves us roughly $1.5 million on dry cleaning over the years.
Price: $150
Norma Kamali Diana Gown
Behold, the supersuit of date night and wedding guest dresses. It’s the exact dress Carrie Bradshaw iconically strutted down the street in HERE. But the fit is phenomenal on those of us who don’t have the ballerina bodies of Miss Bradshaw. The ruching covers up all our lumps and bumps and makes us look the very best we’ll ever look in a little black dress. We wear it with THESE* extremely comfy and cushioned platform heels.
Price: $215
2. The Slip Skirt And Button-Down
Polo Ralph Lauren Denim Western Shirt
And now for the outfit templates! One trick we turn to all the time when we have merely minutes to turn ourselves from swamp creatures to gloriously styled humans is to throw on any button-down shirt we love with a long slip skirt. This is our favorite denim version because it nips the waist but we wrote about all our favorite classic, white button-downs HERE. We often tie it at the waist instead of tucking to avoid extra tucked fabric at the waist, but we also use THIS* brilliant belt-like contraption that makes all ur clothes magically look tucked without tucking it into our bottoms.
Price: $168
Quince 100% Washable Silk Maxi Skirt
Again, Quince makes a flawless 100% silk maxi silk skirt that’s washable and comes in a dozen colors and prints. We have it in white and black but also have mineral yellow in our carts to recreate THIS look for spring/ summer.
Price: $80
Dr. Marten’s 2976 Smooth Leather Platform Chelsea Boots
Boots are a big part of date night because we’d rather have our feet comfily resting in a boot than strangled into a stiletto any day. They’re shockingly flattering with so many outfits, including skirts. The platform gives you height, longer legs, and butt lift, which is most of what a heel is good for. We made our case for these boots with LOTS of photos HERE.
Price: $210
3. The All-Black + One Accent Piece Ensemble
Blazer* | Top* | Pants* | Similar Shoes* (Gifted items included)
Top* | Pants* | Similar Shoes* (Gifted items included)
Aritzia
Standout Blazer
To quote the great Nora Ephron, “Black makes your life so much simpler. Everything matches black, especially black." This whole template hinges on an excellently tailored, quiet luxury black ensemble punctuated by a striking leopard shoe. If you don’t have these pieces already, start with this - the best-tailored, black blazer around. Hands down. We’ve written dedicated articles about it on our own volition - not paid by the brand, because it gives us the best hourglass of our lives instead of making us boxy and shapeless, which is ideal for date night.
Price: $248
Aritzia Posh Tube Top
Strapless tops actually make shoulders look less wide than a lot of tanks and tees that cut into or emphasize the thickest part of the arms. This top has tons of smoothing hold and lots of allure/ potential for a statement necklace to shine.
Price: $98
Aritzia The Effortless Pant™
These are the trousers we’ve been longing for ever since we first saw Katharine Hepburn place her hands in her pockets and waltz her swan-like frame across a room. They drape in such a way to make us look wildly sophisticated and 3 inches taller. We can throw them on when we’re feeling our most “meh,” and we suddenly feel like a model.
Price: $148
The Leopard Shoe
4. The Black on Top White On Bottom
Quince 100% Washable Silk Maxi Skirt
We fell in love with this look when we saw the lovely Lydia Millen putting it together here. It feels new and alluring, but it’s also extremely easy and deeply flattering. The length and cut makes our dream of wearing a white skirt way less scary. You can use the same one we mentioned before from Quince. Add the fitted blazer on top, and you’ll suddenly have your very best proportions.
Price: $80
Spanx The Perfect Oversized Blazer
And here is that 10 out of 10 blazer again. The uses for it are endless.
Price: $248
Vivaia Rumi Mini Square-Toe Slouchy Knee-High Kitten Heel Boots
These are one of the most comfortable heeled boots that we’ve ever worn. They’re breathable and flexible and unlike any other boot. You’ll feel more like you’re in sneaks than heels.
You can use the code CANDIDLY12 FOR 12% OFF.
Price: $269
5. The Going-Out Top And Dark Jeans
Favorite Daughter The Date Blouse
Appropriately titled The Date Blouse, this is that understated but sexy top every woman over 40 should have on hand. You can wear it over a cami or even with a lace bra peeking out. It’s the perfect thing to just slip on with jeans and know you look elevated and elegant. Also, the bottom is a bodysuit so the tuck always, always looks perfect.
Use the code THECANDIDLY15 to get 15% off.
Price: $198
Paige Anessa 31" Wide Leg Jean
And here we share with you the magic, going-out jeans. We wrote a tribute to these jeans after trying them on because they glide over curves and make our butts look lifted. They size in plus, tall, and petite and come in every wash you could want, but we love this faded black for evening.
Use the code CANDIDLY15 to get 15% off.
Price: $259
Beek Catbird Leather Boot
The best blouse. The best jeans. And now, the best boots. This whole look is an investment but because we reach for them more than any other blouse, jeans, and boots, it makes it worth it, and the cost per wear plummets to pennies.
Price: $255
6. The Striped Dress And Jean Jacket
Faithfull The Brand Maretta Maxi Dress
Stripes are always luxe and chic. As our maxi dresses. Put them together and you have a captivating dress look. The exact dress our EIC is wearing above is soled out in almost every size but any long, striped dress you love will work for this look. There’s no way to not feel gorgeous in this dress. We make it a little more casj with a jean jacket, but the dress alone is a star.
Price: $360
AFRM Ashlyn Sleeveless Maxi Dress
Like a sleep dress yet soooooooooo deeply feminine and chic.
Price: $98
Frame The Off Duty Denim Trucker Jacket
We own a startling number of denim jackets. You probably already have one in your closet now that will work for this look. However, we will say that the cropped style will make your waist look smaller and your legs look longer, especially when you’re in a maxi dress. And this is our favorite cropped denim jacket we own.
Price: $328
Paige Reid Sandal
These shoes give us zero foot pain. They balance and ground a more fitted outfit and give us all the height in the world. Again, with ZERO. FOOT. PAIN.
Use the code CANDIDLY15 to get 15% off.
Price: $229
Madewell
The Essential Curve Medium Shoulder Bag
Just a bit of fringe for a bit of fun. A bag like this can elevate any going-out look, even when it’s jeans and a t-shirt, so it’s quite nice to have on hand when we’re really, reeeeeeaally lazy.
Price: $198
At The Candidly, we try a lot of stuff so you don’t have to. We only recommend things we truly love, and that we think you’ll love, too. All products are chosen independently by our creative team, and all details reflect the price and availability of products at the time of publication. If you buy something we link to, The Candidly may earn a commission.
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