8 Date-Night Outfit Templates That Are Supremely Flattering And Gorgeous
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.
Because 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.
But because we love our significant others AND our precious date nights with them, we decided we need a solution. Which we found in the form of a template. Eight of them actually.
We compiled eight 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 Foolproof Leather Pant Look That Every Human Can Pull Off
The Colette Cropped Wide-Leg Pants by Maeve: Faux-Leather Edition
Leather pants intrigue us. They also make us nervous. We worry they’ll be unflattering or that five minutes in, we’ll feel like Ross from Friends trapped in a chafing material that has no business being skintight. But then, we see someone looking so chic and elevated in them that our desire persists. Well, we’re taking it upon ourselves to tell you these are the transitional leather pants that will make taking the plunge both seamless and joyful. They’re the faux leather version of what might be the most flattering cropped pant around, which is to say they’re cut to complement curves: high-waisted, not too loose or too fitted, buttery and smoothing. Plus, they size in tall, petite, and plus.
Price: $148
Lilysilk The Peplos Shirt
The neckline, the drapiness, and the silk add some sophistication to the whole leather pant look. And tucked into a high-waist bottom, this top creates a gorgeous silhouette.
Price: $128
Quince Italian Wool Double-Breasted Slouch Coat
A sleek wool coat will always make whatever you’re wearing under it look more polished and dressed up. By wearing one in caramel over all black, you’re creating a very lusty look that’s classic, but with the leather pant, it has a bit of edge. We love Quince’s coats because the price is excellent for this quality of Italian wool.
Price: $200
Inez Alta
Sooooo, we won’t do a painful shoe anymore. No matter how stunning it may be. Will you? What we will do is invest in one gorgeous heel that’s entire reason for existing is to be as comfortable as it is beautiful, which is the shoe brand Inez’s exact mission. We’d wear this shoe with anything, but it takes the above outfit to a whole new level.
And you can get 15% off using our code: CANDIDLY15.
Price: $258
2. The Easiest Way To Pull Yourself Together When You Have 5 Minutes To Get Out The Door
Quince 100% Suede Biker Jacket
One trick we turn to all the time when we have merely minutes to turn ourselves from swamp creatures to gloriously styled humans is really just to throw on a suede or jacket and a tall boot. And if you mistakenly thought this suede jacket must be fake due to its price tag, you’re in for a treat. It’s 100% real and 100% game-changing. Toss it on over ANYTHING, and you’ll look luxe. Sexy. Styled!
Price: $150
Sam Edelman Penny Wide Calf Leather Riding Boot
Tall boots infallibly give off “I-know-what-I’m-doing-when-it-comes-to-clothes” vibes. We wear this particular pair because they’re gorgeous and they fit over our calves. They also come in black, but we like the contrast of a tan boot with a dark jacket (just like Jennifer’s look above). It weaves everything together without being too matchy matchy.
Price: $200
Madewell The Perfect Vintage Jean
Invest in one really comfortable pair of black, fitted jeans, and poof, you have a pair of jeans fancy enough to wear out and with practically anything. This pair holds us in in the most flattering way. It’s perfection on curves, fitted but not too tight. And they come in petite and tall.
Price: $128
3. The Prettiest Way To Wear A Fitted Dress When You’re Curvy But Want A Little Coverage
A New Day™ Women's Cami Midi Bodycon Dress
Sometimes we go out searching endless hours for a dress that looks great on our bodies, and other times that dress finds us. And it’s under $30. This bodycon dress is stretchy, slimming, and sizes up to 4X, so it works really well on curves. And picking a long, not-too-thick piece of outerwear is an excellent option for when we want a little more coverage. Which brings us to…
Price: $28
Able Kimberly Trench Coat
A whisper thin trench works so well as an outer layer that doesn’t drown out the rest of our outfit. This one is so light and airy and the way the tie cinches the waist is so flattering, not to mention convenient. It also comes in brown sugar and sizes to 3X.
Price: $198
Z Supply Mason Knit Coat
If you’re like us and want to go the cozy route, there’s nothing more joy-sparking than this long, clean-lined coat that happens to be the softest, almost weighted knit material. It’s oversized and cocooning while still looking sleek and formal. And the colors are all perfection.
Price: $199
4. The MILDLY GENIUS BLACK AND WHITE ENSEMBLE
By Anthropologie The Tilda Maxi Slip 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. And with the fitted blazer on top, we suddenly have our very best proportions.
Price: $98
Spanx The Perfect Oversized Blazer
Once again, a black blazer that’s juuuust oversized enough for you to be able to move in it but also has that tailored shape that makes you look clean and crisp is something worth spending on. We’re willing to bet you’ll wind up wearing this blazer 10x more often than any other piece of outerwear. It looks perfect over dresses and skirts, especially the above maxi.
Price: $168
5. The Best Way To Feel Sexy(ish) When You Don’t Love Showing A Lot Of Skin
By Anthropologie Long-Sleeve High-Neck Baby Rib Top
Looking sexy isn’t always about showing skin. Choosing something tissue soft and fitted like this turtleneck makes us feel comfortable and like ourselves, but it’s soooo complementing to our curves, guys. We swear. Tuck it into a smoothing wide-leg pant (see below), add a cushioned heel, and yes, you will look chic and sexy, but you will also feel chic and sexy, which is really 97% of the battle.
Price: $48
The Colette Cropped Wide-Leg Pants by Maeve
And here we share with you the “magic”pants. We wrote a tribute to these pants after trying them on because they fit so well and smoothed us like a layer of frosting. They size in plus, tall, and petite and come in every color you could want.
Price: $120
Jenny Bird Icon Hoops
And in one itty-bitty, last-minute move, your whole turtleneck ensemble is suddenly street-style chic. These hoops are perfect in size and have the most comfortable backs we’ve ever worn.
Price: $110
Aerosoles Cosmos
These are one of the most comfortable heels that we’ve ever strapped onto our feet. You won’t even feel like you’re in heels.
Price: $135
6. The Ideal Ensemble When You Can’t Stand Wearing Anything Tight
Z Supply Modern Slub Tee
It starts with a perfect-fitting, whispery soft tee. And this is THE one.
Price: $39
Good American Velvet Sculpted Blazer
Once again, the ideal not-too-tight but supremely well-shaped, nipping blazer. Which means we get to look like we’re wearing something clean and fitted when in fact, we’re very comfy. And this time it’s in velvet, which makes it much more festive and much more fun.
Price: $199
Everlane The Way-High® Sailor Jean
These might be the most comfortable jeans we’ve ever put on our bodies. The stretch is unreal without an ounce of sagging. But it’s the wide-leg, not-too-exaggerated sailor shape that makes them look a little more like a trouser, and therefore, they dress up extremely well.
Price: $128
Nisolo Dari Commuter Boot
One perfect, perfect pair of comfy, block-heeled black boots is all you actually need to make any outfit into a “going-out” outfit.
Price: $250
7. The Outfit You Wear To Show Off Your Legs And Only Your Legs
Pomander Place
Noir Vivianne Dress
We get spooked by the word short, because we’re not 22, but with tights and tall boots, wearing something shorter can make us look chic and wintery and long-legged in ways a knee-length or longer dress just can’t. The fact that this dress isn’t tight also balances the fact that it’s on the shorter side. Add an oversized jacket, and we swear, you’ll feel invincible.
Price: $128
Anine Bing
Quinn Houndstooth Blazer
This blazer gives us the exact proportions we’re looking for, especially over the above dress with tights and boots tall enough to supply that extra bit of coverage.
Price: $360
Vince Camuto Sangeti Boot
A comfy block-heeled boot that our feet don’t suffer in is very difficult to find. Which is why we never seem to shut up about these. And it comes in wide calf!
Price: $229
8. The Most Flattering Pants Outfit For Nights You’re Feeling Meh
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
M.M. LaFleur The Moreland Jacket - OrigamiTech
We’re pretty thrilled when we find a tailored little one-and-done piece of outerwear that’s also cozy. And this one amazingly is washable! We love it in olive over an all-black outfit, but it also, naturally, comes in black itself.
Price: $335
Skims Seamless Sculpt Brief Bodysuit
We hesitated to say it at first but Skims makes suuuuuuuch good shapewear. We wear their bodysuits as tanks ALL the time. This one nips our waist when paired with a wide-leg pant, and the neckline makes it a little sexier, so it doesn’t seem like we’re in workwear.
Price: $72
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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