Date Night – The Commitment, The Wardrobe, The Magic


It was nearing the end of the summer of 2022, and I was deep in planning my family’s fall schedule. Both my daughters would be going to school on varying days and times, and we’d have them dabbling in some afterschool activities, all of which required different drop-offs and pick-ups by me.

We were adjusting to my husband returning to the office three days a week post-Covid. I was poorly mapping out my flexible but not fully predictable client schedule, volunteer commitments, and other responsibilities. We were cutting my full-time nanny’s hours in accordance with our kids’ new school schedules.

The calendar was daunting, to say the least, and I felt a bit overwhelmed at the helm of it all. As I shaped what my family’s life would look like for the next several months, it dawned on me that my husband and I were like two ships passing in the night. Our only alone time together was really an hour or so that we snuck in after the girls finally fell asleep. Most of the time, all the energy we could muster was for watching some Netflix on opposite ends of the couch.  

My pen then began to scribble in a hard commitment one night a week – date night with my husband. Would my husband be up for it? Would my nanny agree to work late one night a week? Would I be able to rally after a long day when pjs seem like the only option? Would our kids be ok without us for one night a week?  

As it turns out – he was. She was. I was. They were. And thus began an almost weekly date night ritual for my husband and I. 

Now, date night with my husband came with the benefits you might expect – a great time to connect with my husband, a chance to enjoy a meal without getting up a million times to get one more thing for the kids, and yummy food I didn’t have to cook or clean up. 

However, as a fashion stylist, it also came with an opportunity to fully exercise my style in a way that I hadn’t in a long time – still super true to myself, but a little bit less restricted, a bit sexier, and a bit more pre-kid. After all, I didn’t have to worry about my hemline while crawling under the table to pick up dropped crayon after dropped crayon.

After my experience and commitment to date night, I’ll stand by two pieces of advice. One from the mom and wife in me – pen in that date night, whether once a week or once a month. It’s good for you, your partner, and your kids. The second is as a stylist – use date night as an opportunity to take a risk with your personal style you might not normally do in your day-to-day.

Here is some date night outfit inspiration by personal style archetype. And if you don’t know what yours is, start by asking yourself how you want others to perceive you when you show up.


Pull out one of your classic Oxford shirts and add a faux leather pant in a classic cut. This Oxford button-down will double for mommy duty as it’s virtually spill-proof, and these faux leather pants are a universally flattering favorite of mine. Push the envelope further by opening the shirt’s neckline to show off your décolleté or a lacy bralette. Pops of red and sparkle in your accessories elevate from the everyday.

classic date night look.

Oxford Shirt l Faux Leather Pants l Classic Red Lip l Cap Toe Slingbacks l Red Handbag l Heart Pendant


Being feminine and romantic is a perfect combination for a date night, but it’s also your chance to be a bit more sophisticated. Start with a floral dress in unexpected hues – no sugary sweet pastels here. Lace cut-outs add to the allure. A black boot and blazer help to elevate the look for the evening, while a bow bag, sparkly flower earrings, and light pink wash on the lip maintain that girly vibe.Floral Dress l Black Blazer l Black Boot l Green Bow Bag l White Floral Earrings l Pink Lip


Whether casual is your overall aesthetic or your particular date calls for something more laid back, it’s possible to look chill and like you put in the effort. First, start off with a great-fitting pair of jeans. This pair is a cult favorite and easily dresses down or up. Then think about adding a top in a casual fabric and style, but with a twist. Strategic cutouts around the shoulders, neckline, or back are perfect for this. Cool sneakers and paired-back accessories will keep the look fresh. Lastly, a multi-facet bag that can go from cross-body to shoulder to clutch in a sporty fabric will complete your outfit. My favorite casual lip product is a balm with a bit of color and flavor.

Cutout Top l Pinch Waist Jeans l Gold Hoops l Black Belt l Black Bag l Sneakers l Balms


If you are a bit edgier when it comes time to dressing, here is your chance to wear the things you wouldn’t in the drop-off line at school! A bodycon sweater dress makes for a great start. I’d layer it with an ultra-cool girl harness with some embroidery that keeps it from being too dominatrixy. Sleek black boots and a killer clutch keep the look polished. Finish off with some mixed metal jewelry and a slightly smokey eye.

Red Sweater Dress l Embroidered Harness l Black Boot l Clutch l Earrings l Eye Shadow Palette 


If you are an eclectic dresser, the goal should be to wear visually interesting pieces without looking clownish. The trick for me is picking refined and elevated pieces that simultaneously make people stop and say wow, that’s interesting. For date night, I recommend a well-designed dress with an unusual element. The diamante chords at the neckline do a great job of making this piece unique. A super sparkly boot is an unexpected pairing, and a red box clutch with spheres rivals a work of art. Stand-out jewelry adds another layer of visual intrigue, and eyeliner that shifts from an inky blue/purple to rosewood is a subtle, sexy nod to eclectic dressing. 

Maxi Dress l Red Clutch l Crystal Boot l Winged Earrings l Stone Ring l Color Shifting Eyeliner

 What’s your favorite date night look? Tell us what you love in the comments below.

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After spending over ten years living in NYC, Katie moved to Westchester County with her husband in 2016 to start their family. They have been blessed with two beautiful girls Eva (2018) and Carolina (2020). Katie began her career working at some of NYC’s top advertising agencies leading strategic media efforts for Fortune 500 clients in the fashion/beauty space. After a series of events, Katie decided to pursue her lifelong passion and work more deeply in the style realm. She honed her chops, training to become a certified personal stylist under two industry vets. Soon after she founded her personal styling company, Style Outside the City (@styleoutsidethecity). Her business focuses on helping moms who have lost a bit of their creativity and confidence in dressing with all of the changes motherhood (and suburbia) brings. Katie loves to help women truly understand the mental side of style as a way to express themselves and hone their visual identity. She also brings a technical eye to personal style by educating on body shapes, fabrics, closet organization techniques, and shopping skills. She works with clients one-on-one to help them build style and a wardrobe that makes them shine.