It’s the question that comes just after “What if we run out of things to say?” and just before “Should I wear heels?” Figuring out the best outfit to wear on a first date is about striking the balance between feeling like yourself and dressing for the moment. You could be heading to a wine bar, a riverside café, or somewhere a little more unexpected, but wherever you go, it’s the outfit that sets the tone.
In this WalG styling guide, we’ve pulled together a few first date outfit ideas based on the mood, time, and place - all styled with comfort, ease, and understated charm in mind.
1. The effortless midi dress
When in doubt, go for a dress that does the talking for you. A midi in soft satin or crepe is a perfect choice for evening dates; relaxed but refined, and easy to dress up or down. A wrap silhouette can give a little movement, while a slip dress is best for layering with a jacket if you’re unsure of the weather or want to keep things feeling low-key.
For example, the VALENCIA Cut Out One Shoulder Midi Dress, cut to skim the body. Style with a strappy heel and finish with simple silver jewelry for a look that feels pulled together without trying too hard.
2. The classic mini dress
Mini dresses are a classic first date choice for a reason: they’re fun, flirty, flattering, and endlessly versatile. Whether you’re headed out for candlelit cocktails or keeping it casual with a late-morning coffee, the right mini can set—or shift—the mood. It’s all in how you style it, of course.
Take the RUE Chain Mini Dress in navy blue. With its sculpted silhouette, low back, and statement chain straps, it’s made for first dates where you want to feel a little more daring. Wear it alone with a barely-there heel for dinner and drinks, or tone it down with a jacket and boots for a lighter affair— the choice is yours.
3. The jumpsuit
There’s something instantly polished about a well-cut jumpsuit. It’s the kind of piece that takes care of itself. Simple and streamlined, but just different enough to be…unexpected.
Structured styles in satin work well for dinner dates, while softer silhouettes feel right for something more spontaneous. Look for details like halternecks, wide legs, or open backs to add interest without overcomplicating the look. One of our favourites? The LANEY Red Strapless Jumpsuit.
The beauty of a jumpsuit is how easily it transitions: it can feel relaxed or elevated depending on how you style it. A leather jacket gives it an edge, a tailored blazer makes it sharper. Add a heel if you want height, or keep it grounded with a sleek boot and minimal jewelry.
4. The blazer
A blazer has a quiet way of pulling everything together. It’s sharp, it’s structured, it has a little preppy edge to it, whether it’s layered over a mini dress or paired with tailored women's dress pants and a slim tank. The key is in the cut: lightly tailored with a bit of length through the body to balance proportions and suggest ease.
For first dates, we love it worn open over a satin cami and denim. Push the sleeves, tuck your hair behind one ear, and add something simple at the neck. It’s an outfit that works whether you're staying for one glass or slipping into somewhere unexpected afterwards.
5. The backless top
There’s something undeniably magnetic about a backless top- it’s effortlessly cool, yet carries a touch of allure that sits just right on a first date. One of our favourites is the CRISSY Black Backless Top, also available in deep wine and forest green. It’s equal parts flirty and refined, with soft, drapey sleeves, elegant ‘V’ neckline, and open back with waist tie detail.
Pair it with our high-waisted BUZZ Black Pants (also available in navy blue and dark brown): softly tailored with a wide leg to balance the drama of the top. Finish the look with a peep-toe heel, gold hoops, and a swipe of lipstick. The result? The perfect outfit for a first date that starts with cocktails and ends with “shall we stay for one more?”
Find the best outfit to wear on a first date with WalG
First dates are all about feeling comfortable, confident, and completely yourself. Whatever you’re planning, from low-key coffee dates to romantic evenings in the city, WalG has pieces designed to flatter your figure and match the mood.
Find your perfect silhouette with WalG London in our collections, or browse our Style Inspiration page for even more inspiration on what to wear on a first date.
