It's a Date
What to wear for a date night, GNO, or simply a good time.
Today I’m answering another client FAQ1 that I hear in nearly every session: what to wear for a date night. More specifically, what to wear to feel hot - sexy isn’t a word all of us can relate to, but somehow hot is more of a universal goal - comfortable, unfussy, and ultimately like oneself. If I’m being honest, I tend put the same amount of care, if not more, into a Girl’s Night Out so I’m lumping that in here as well. An outfit that makes you feel like a million bucks while also accommodating a full serving of pasta and a shared bottle of wine, table fries and a couple Negronis, or an evening spent in blissful silence eating popcorn and peanut M&M’s, sipping on a crispy DC, while watching Ryan Gosling’s latest flick. I hear this nearly as often as “I struggle with tops2” and it’s inspired me to share my ideas and suggestions here.
My husband would argue we haven’t had a date night in months despite having a 12 year old built-in babysitter at home, as someone - my youngest - always seems to be on the verge of, in the middle, or having just finished throwing up. Regardless, I’m never not prepared for a good time, so I’ve come up with some outfit formulas that will take you from date night (first or fortieth), to girls night, to really anywhere after 5 pm. These formulas utilize items you probably already have in your closet, so take the inspiration and run with it to a romantic dinner for two.
Fun Top + Jeans: the Millennial formula is tried and true for a reason. Nothing beats a great pair of jeans that make your butt look fantastic and a good old fashioned Going Out Top. These days my tops tend have more coverage and are bra friendly compared to the longline polyester cami of yore and are made of naturally luxe fibers like cotton and silk. But if you’re feeling adventurous you can go for an embellished halter, an asymmetrical mesh tank, a sheer button up, a crop top, or a feathery fringe shell.
Vintage Levi’s or a modern day version with just a little bit of stretch* are my go-to, but a wide leg style would feel very cool here. Finish it all off with a mesh flat or kitten heel sandal, a great pair of earrings, and a blazer thrown over your shoulders.
Fun Bottoms + A Simple Top: the youths have inverted our outfit formula to suit their own taste, and even though they’re claiming many of our early aughts looks as their own, I’m not mad at it. Trade your solid denim for a striped pair, grab a a colorful trouser, silk PJ style pants, or opt for a skirt with a beaded mini, a powder pink skort, or a washed silk maxi in a tropical hue. Fun doesn’t have mean colorful or patterned, it can be achieved through silhouette as well, so grab a pant with volume and structure if that’s more your speed.
A simple top can be a tee, a tank, or a good old fashioned button up shirt, barely buttoned of course. You don’t have to limit yourself to black or white either, play with the colors within those fun bottoms for for a coordinated look. And because your pants (or skirt) are a party all on their own, keep your shoes and accessories neutral-ish.
Blazer as Top: a failsafe formula that I’ve mentioned one or two times before, there’s something pretty sexy - there I said it - about a blazer worn with next to nothing underneath. It’s akin to an oversized white button up worn over a black lace bra, something borrowed from the boys but made overtly feminine.
Double breasted styles often offer a little more coverage if it feels scary to go - almost - commando underneath, otherwise put on your prettiest bra and your favorite blazer. Have fun with texture and silhouette, go for linen, satin, tweed, suede, or leather in oversized, fitted, cropped, or cutaway styles, and let’s not forget some color. Some of my best blazers are second hand, so if you’re shopping beyond your closet, I recommend looking on Poshmark or TRR first.
Speaking of blazers, I was interviewed by Kitty Gou at The Strategist months ago, and just now found the article. Needless to say, I’m thrilled to be included amongst the very stylish and knowledgable panel of experts, and I obviously have a lot of opinions on blazers.
Pair your blazer with denim, soft pants, a sheer maxi, or extra long jean shorts. Layer a couple of necklaces to accentuate the bare neckline, sandals to keep it springy, and a fun bag to finish it off.
A Matching Set + Bold Jewelry: ideally with soft pants, aka something with a drawstring or elastic waist, or Pull On Pants as they’re being called here on Substack.
I’m sure I’ve said this before, but I love a set and depending on the style you pick, they’re basically pajamas you can wear in public. If you’re not into pajama adjacent clothing like I am, look for a set with structure or defined shape via fabric, smocking, or tailoring. Not into pants? Try a skirt and top combo, or shirt and shorts. Options abound in linen, silk (with a perfectly mismatched shirt), taffeta, denim, and cotton; woven, crochet, or knits; in solids, stripes (with this top in particular), and patterns.
Whatever set you choose, go bold with jewelry; big earrings or a funky ear cuff, a long pendant or tassel necklace layered under your shirt for a peek-a-boo moment, a stack of bracelets, and of course, mix your metals. Choose colorful accessories that compliment or contrast the set, add extra texture with woven leather, and then tie a sweater around your waist for good measure.
A Dress + Something Funky, Edgy, or Sporty:
I’ll be honest, as a former Dress Person, I really only break them out for Special Occasions (with a capital S and O) and summer. I live a very casual life, as many of you can relate to, and I no longer need - or at least feel compelled - to wear a dress all that often. That being said, I’m trying to break the habit and bring my many, and there are so so so many, dresses back into the regular rotation.
My advice for any time of day, but especially date night, is to balance out the femininity of a dress with something funky, edgy, or sporty, bonus points if you add more than one. Chunky, metallic sandals, a colorful windbreaker, or an absurdly oversized jacket (in denim or leather) are all easy add-ons that bring the outfit from prim to very very cool. Lucky for all of us, Kelly Klein recently wrote about dressing down those fancy pieces and said “an oversized jacket has a way of making whatever is underneath feel cooler almost automatically.” Wise words from one of the wisest - and most stylish, duh - women out there.
Midi dresses are my focus for this exercise, but grab a mini if that’s more your speed. Play around with volume with a full skirt and big jacket (thank you Madeline Rose Nachbar for the hot tip on this green beauty) like I did, or balance the oversized outerwear with a slim slip dress or body skimming knit. Either way, opt for shoes that add that edge, funk, or sporty touch with chunky soles, slim sneakers, or studded leather. Pick some ladylike sunnies, but don’t forget to add a beaded necklace* or two.
Jeans + A Tee or Tank + A Good Jacket: jeans and a tee are basically the perfect outfit base, even and especially for a date night. Just make sure the jeans are comfortable enough for that big bowl or pasta and/or movie theater popcorn mentioned above. Maybe they look great* too? Stretch isn’t necessary, but room to breath is.
The tee should be light weight yet structured, or maybe it’s a little sheer, slim fit but not tight*. Your tee is just as important, but your bra even more so. I’ll let you decide what bra is best for you, because boobs, but I like this one, this one*, and I’m very excited about this one* that I just received.
Your jacket options are endless, leather, blazer, a leather blazer, lady, denim, suede, workwear…you get the idea. For full length jeans I like a delicate sandal, flip flop, or slim ballet flat, for an ankle length or crop you can wear the same or pick a high vamp flat, loafer, or a sandal with more heft. If your jacket has pockets, skip the bag and stick your phone, ID, and lipgloss in your pocket.
Monochrome: another favorite formula of mine, pick a color and run with it. It’s spring, nearly summer, so all shades of white, cream, and tan come to mind.
As I’ve mentioned, texture is key to make a monochrome look shine. Layer linen, crochet, denim, leather, and suede for depth and contrast. You can also create contrast by mixing styles (I mixed tailored with boho with sleek above) that on surface level can feel a little incongruent, but actually makes so much sense. You can add a pop of color or ground it with black, but you really don’t need to, there’s plenty of interest already.
Whew! Okay, eight outfits to get your sartorial juices flowing. That was fun! What’s your date night/night out/GNO outfit formula?
ICYMI, I invited Lydia Lauer to share her favorite spots around Portland last week. The series3 is very niche, and selfishly motivated, but she created a pretty dreamy day spent in SE Portland. Then Ariane Anusbigian kindly gave us a peek inside her bag4. It should come as no surprise that the contents are as delightful as she is. Thank you ladies, I’m having so much fun with both of these! If any of you out there are interested in contributing or know someone who you think should be featured, send me a DM!
Thanks, as always, I’m so happy you’re here.
Talk soon,
xx FANNY
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More on that topic coming soon.
Now that’s a hot date! I literally cannot pick a favorite, I love them ALL.
The green skirt?! That green jacket?! So good.