The Tip Jar #4: How to Make an Impactful Impression with Date Night Looks

Inject personality into your wardrobe with elevated statement tops and unique accessories

I hope everyone had a refreshing holiday season spent with those who matter most. Now that we’re all back in the office, it’s time to get back to our regularly scheduled programming on Tuesdays. We’ve got some great content planned for the year, and I’m excited to have you along for the ride. So, let’s dive in!

Last year, we launched The Tip Jar, a monthly column on Musings of a Merchandiser dedicated to tackling readers’ ultimate style questions. We covered various topics, from navigating 2024’s evolving office dress codes to breaking out of a “dadcore” rut after a cargo shorts spree at REI. We also helped a reader in her 40s rediscover her style and regain confidence in her outfits. To kick off the new year, I’m answering an enjoyable request.

I tried on everything I owned and still had a messy outfit for my date on Friday night! My whole wardrobe screams going to the office, and every date night look feels way too business casual—it’s just not the vibe I’m going for. I need ideas for date night outfits that feel fun and effortless but don’t involve lace bustiers or blazers. That’s just not me.

Many of us are making New Year's resolutions, whether it's putting ourselves out there more, finding a partner, or simply committing to more meaningful experiences outside of our homes. With limited time during the week (especially after work), it’s super challenging to carve out time for a night out—whether you're in a committed relationship or not. Add on figuring out the perfect outfit? Forget about it, you might as well stay in. Today, I’m here to help alleviate that pressure with fantastic options beyond the conference room, suitable for both genders and various occasions. The bonus? These items might help you land that second date and beyond.

Turning Heads With Personal Flair

Recently,

Lindsay Sword

wrote an amazing article making the case for celebrating the timeless appeal and versatility of the 'black top and blue jeans' combination. While there’s no denying the ease and elegance of this classic pairing, I’d argue we all have a little more creative juice in the tank when it comes to putting outfits together. Sure, it’s tempting to rely on ‘old faithful’—that one black item that always pairs so well with jeans—but consider this your 2025 push to think a bit outside the box and inject more personality into your wardrobe.

On that note,

Kelly Williams

explored the buzz surrounding Joanne's creative 'going out tops' in Nobody Wants This. Her analysis of why Joanne's outfits have made such an impression offers a fresh perspective, particularly in light of the shift away from the quiet luxury trend. It’s a great reminder that even small, thoughtful details can make a big impact.

On Top of it All

So, here’s a fresh formula to try: Start with your favorite color (or pattern) — we already know it flatters your eyes and complexion, so it’s perfect as your new outfit foundation. Next time you’re scrolling through sites or browsing stores on a Saturday, look for that color in a top but don’t settle for basic. Skip the plain crewneck sweater and opt for something with a little extra detail—think ruching, interesting stitching, a hint of lace, a bold shoulder, a unique collar, or a statement sleeve. To help spark your creativity, I’ve rounded up a handful of great examples to inspire your next look. Grab your favorite pair of jeans and let’s go!

These tops each bring something unique: Free People’s Angelina Bodysuit delivers a sultry, fitted silhouette, while Nation LTD’s Daisy Top in Galaxy Blue is effortlessly chic. Simon Miller’s Loch Button-Up features a modern stripe with a peek-a-boo back, and Norma Kamali’s Shoulder Pad Long Sleeve Crew Top creates a bold, structured look with power shoulders. Let’s not forget pattern play: Damson Madder Tish Shirred Cami in leopard print offers flattering shirring, while Reiss delivers a polished, tailored look with surprise slits on the sleeves. Rachel Comey’s Reno Top in chiffon has a relaxed, airy fit with ruffled details, while Solid & Striped’s Babetta Sweater in bright red is bold and cozy with dramatic sleeves. Finally, Reformation’s Rose Knit Top adds a timeless ruched design, and Susana Monaco’s Mock Neck Gathered Front Top offers elegant gathers in deep navy.

For the men out there, my husband owns this Outerknown Chambray Utility Shirt, the perfect relaxed yet elevated vibe, or for a minimalist coastal style, check out Mollusk Surf Shop’s Beacon Sweater, or Todd Snyder’s Wool Cable Crew for classic warmth in a vibrant red.

Finishing Touches That Wow

If you’re stocked up on tops, here’s a secret: accessories are the real game-changer. I learned this on my first date with my now-husband. Picture this: I walked in wearing a striped turtleneck and corduroy overalls—definitely not the chicest choice, but it was my vibe (I love channeling my inner 5th grade self). He loved it. What he loved more, though, was the Kate Spade bangle I wore, shaped like eyeglasses. It caught his eye instantly and turned into a fun conversation starter. The right accessory can completely elevate an outfit and leave a lasting impression.

Last year, we talked about novelty bags being the fall wardrobe staple, and it still rings true this season. If you're done shopping for tops, focus on adding that one unique piece to make your look pop.

The Novelty Bag: The One Trend You Need This Fall

For those looking to elevate their accessory game, this curated selection offers something for every style. The Jennifer Fisher Small Puffy Heart Earrings provide a softer, romantic touch, while the Lele Sadoughi Pave Kiss Brooch radiates bold charm with its vibrant lipstick-red crystals. Add an extra spark to your belt with the textured B-Low’s Joshua Calf Hair Belt or the sleek, polished Rag & Bone Highline Belt. Playful statements like the timeless Rebecca de Ravenel Ladybug Red Earrings or the charming Lele Sadoughi Rootbeer Polka Dot Bracelet bring character, while BaubleBar’s Jaskamal Earrings are a feast for the eyes. Celebrate the year of the snake with Oscar de la Renta’s Crystal Snake Ring, or make a bold neck statement with the Oak and Luna bubble up initial necklace with diamond. The Lizzie Fortunato Mini Arp Earrings in studded silver are a must-have, and the Rosette Pearl Drop Earrings from Petit Moments add floral elegance. Layer up with the Ben Amun Set of 3 Thin Bangles, and finish strong with the Lizzie Fortunato Shadow Drop Earrings to bring unique flair to any outfit.

For minimalist men with a dash of flair, the Mejuri Slim Rectangular Signet Ring adds a modern edge, and the Miansai Ira Chain Bracelet in polished sterling silver exudes understated sophistication. The Mejuri Black Onyx Pendant Necklace offers sleek elegance as well.

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As we step into a new year, it’s the perfect opportunity to refine your style with thoughtful updates. Whether it’s a striking accessory or a statement top, small changes can make a big impact. I hope these ideas inspire you to approach your wardrobe with a fresh perspective—effortless, intentional, and uniquely yours. And as always, keep your style questions coming in the comments section for next month’s Tip Jar. Here’s to a confident and stylish 2025.