My Rules for Building Incredibly Chic Date-Night Outfits Are So Easy to Master

Plus, how take your looks from day to night.

Christie Tyler in a multitude of neutral outfits for day to night
(Image credit: Christie Tyler)

I love a date night. Getting dressed up, showing off any new purchases, and most importantly, spending time with the person you love the most – to me, there is nothing better in this world. However, sometimes dressing for your next night out can be tricky.

I find myself asking the same questions over and over as I put together my looks: When is it too much? Are my pieces too tight? Am I showing too much skin or too little? I'm a firm believer in wearing pieces that make you feel the most comfortable and the most sexy, whether that means more skin or not—but I also love bridging that gap by pushing a bit of a creative boundary.

I love feeling sexy in a way that feels very me, which most likely means opting for a minimalist-inspired look with unexpected elements. And, if we can convert that look from day to night with a simple change? I’m all ears. Ahead, I break down two of my date-night outfit "rules" that you can return to for inspiration whenever you're in a style rut.

Rule #1: Switch Out Your Bag and Shoes

Christie Tyler models an easy date night outfit

(Image credit: Christie Tyler)

This one is truly simple enough, but it works wonders. I was wearing these vintage jeans and a vintage Armani top, loafers, and my huge everyday bag for a day of meetings and writing. When my boyfriend called to say we were headed to sushi for date night, I quickly swapped out my shoes for a cheeky wedge heel and said goodbye to my tote, opting instead for a satin handbag for the evening. Adding some dramatic drop earrings was the cherry on top.

Rule #2: When Wearing a Dress, Pair it With a Flat

Christie Tyler styles a date night outfit

(Image credit: Christie Tyler)

Another look I love for a date night is an elegant, comfortable dress with a gorgeous flat shoe, especially one with a pointed toe peaking out from under the hem. A dress with a pair of heels, of course, exudes formality—when paired with a flat shoe or a larger bag, it can still retain that elegance with a touch of casual energy. You could have worn this look all day (and hopefully did), and no one would say you were overdressed. It is all about balancing formal and informal elements.

Rule #3: Add Texture That Speaks Volumes

Christie Tyler shares a date-night outfit

(Image credit: Christie Tyler)

I am a firm believer in doing one thing with each outfit. That can mean sticking to one texture, one print, or one metal element per look. I immediately thought of this Dries Van Noten textured blazer. I paired it with a skirt and loafers during the day, but it would look so elevated with heels for date night. Letting the blazer speak in its beautiful, silk texture is enough. That is your sex appeal, your conversation piece, or your formality.

Pairing it with an all-black look or keeping the rest tonal is the perfect way to show you are putting in effort while maintaining restraint, so no one element dominates. That conversation between effort versus restraint is what style is—how much effort versus restraint is up to you.

Rule #4: When in Doubt, Do Less

Christie Tyler

(Image credit: Christie Tyler)

Skin is a big part of this conversation. I’m a believer in less is more—and that applies to layers, too. There’s something incredibly liberating about freeing up a bit of skin and not bogging a look down with excess. I always come back to Coco Chanel’s advice: take one thing off before leaving the house. An unbuttoned silk shirt—maybe by one button too many —tucked into corduroy trousers with a low heel feels quietly confident. It’s a kind of sex appeal that doesn’t feel excessive, just intentional.

Christie Tyler
Contributing Editor

Christie is a content creator, model, and the co-founder of Vollective; she also runs a popular Substack. She's marketed for brands including CHANEL, Louis Vuitton, Hèrmes, YSL, and more.