Melissa Epifano
It's one thing trying to determine what to wear on date night, it's another completely trying to figure out what to wear on a first date. First impressions hold so much weight, and it's so easy to get caught up in small details or instantly feel like you have nothing to wear. Add to that the fear of not wearing the right outfit for the occasion, and you'll feel utterly overwhelmed. You're not alone, and fortunately, there are some outfit formulas that make it much easier to get dressed for your first date.
A skirt and nice jacket is one of the best combinations for a first date. Lucy's satin skirt and suede jacket is an ideal pairing.
I'd argue that the most important thing is feeling like yourself. It's less about copying a trend or trying to reinvent your wardrobe hours before you leave, and more about choosing an outfit that makes you feel your best. The less you worry about what you're wearing, the more you can relax and enjoy getting to know your date—and that's where these seven formulas come in. We broke it down by date activity to give you inspiration for outfits that are fit for each occasion. You'll find both elevated looks that are best suited for nicer dinner dates and more casual outfits that work for coffee meets and strolls around the park.
Scroll on for seven stylish outfits to wear on a first date, plus shoppable options so you can complete these looks if you're missing a piece or two. We're sending lots of luck your way!
7 First-Date Outfit Ideas I Always Recommend:
1. Dinner First-Date Outfit: Midi Skirt + Black Jumper + Heels
Style Notes: Going to dinner calls for an outfit that's elevated but easy to wear, whether you're at the chef's counter seat on bar stools or sitting in a booth. You can never go wrong with a high-neck jumper and knit midi skirt. Add a pair of minimal heels and you'll feel ready for your first date (even if the nerves are still there).
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So soft and easy to tuck into a skirt with a belt.
The wool blend will be warm enough for all your autumn and winter dates.
Mesh heels are the perfect date-ready take on the mesh flat trend.
2. Drinks-After-Work Date Outfit: Wide-Leg Trousers + Simple Top + Flats
Style Notes: As elegant as a skirt or dress is, I find trousers is often the safest bet for a drinks date. If you're on a tiny, swiveling seat or standing in a noisy pub, trousers offer a little more comfort and still look infinitely chic. Dawn's additions of a sleek, high-neck top, headband and belt are the perfect finishing touches.
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An ideal layering top for autumn.
These trousers come in a versatile grey and beige.
Comfortable but elegant at the same time.
3. Dinner-and-a-Show First Date Outfit: Black Maxi Dress + Leather Jacket + Smart Flats
Style Notes: Off to an event with a nice sit-down dinner beforehand? What a treat! I think there's no better occasion to show your styling abilities. Look to Abisola's gorgeous outfit. A sleek LBD with a cool leather jacket is a concrete look that'll never let you down.
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A gorgeous option for so many nice occasions.
Boxy leather jackets are trending this year, and I love the flat pockets on this one.
These feel as sleek as heels but are flats.
4. Coffee First Date Outfit: Slip Skirt + Long-Sleeved Tee + Boots
Style Notes: The midi skirt is a classic for a reason. It's universally wearable and can be dressed up or down depending on your date activity. For a coffee date, I love Liv's idea of pairing a sleek long-sleeve top and heeled knee-high boots with your skirt. It looks effortlessly stylish, and you can choose any combo of skirt and top to really make it feel like you.
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The neckline on this top feels particularly elegant.
This Reformation dress creates the sleekest hourglass silhouette.
A chic boot to wear with skirts, dresses and trousers.
5. Active First Date Outfit: Leggings + Zip-Up Top + Coat + Trainers
Style Notes: If you're doing something more active on a first date, like a long walk through the park or even playing a game of tennis, you want to be prepared but still feel put together. Tandya's look has all the components down. Wear a matching set, like leggings and a zip top and pair this combo with cute (but functional) trainers and a nice coat. You'll be ready to go but feel stylish enough to grab a latte after if the date's going well!
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Studio Nicholson has some of the best tailoring I've seen, and this trench is no exception.
You can never go wrong with an all-black matching set.
Adanola's leggings wear incredibly well, even after years of washing.
6. All-Weekend-Long First Date Outfit: Trench Coat + Cardigan + Jeans + Boots
Style Notes: Got a first date planned for this weekend? You might be meeting for a casual walk or a coffee and stroll, that turns into a visit to a gallery, that turns into drinks, that turns into dinner...in which case you want to feel your best and not get caught out in an uncomfortable outfit (I've been there before with awful blisters on a first date) that can't work for all eventualities. A trench coat with jeans and your favourite pair of boots is ideal. It's casual but stylish all at once. You won't feel too warm or cold either.
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The Clyde coat is famous for its styling versatility, and the chocolate brown version is primed and ready for autumn.
The perfect cardi.
These jeans will go with so many tops during every season.
The perfect size for carrying all of your essentials.
My dream boots.
7. Lunch-Break First Date Outfit: Tailored Trousers + Fitted Blazer + Loafers
Style Notes: First dates after work are common, but what about during work? No, we don't mean on company time, but instead what if you're just popping to Gail's on your lunch break to get to know one another? I, in fact, still meet my husband during lunchtime to catch up, despite working for different companies located down the road from one another! Either way, one wants to carry around an entire change of clothes—and lug it to the date. Amaka has the right formula. A waisted blazer or cardigan is pretty and suitable for work and first-date drinks. For a fun finishing touch, wear a cool pair of shoes (whether that's cow-print loafers or bright heels) to pull your personality through.
Shop the Look:
The trending waisted blazer is such a chic silhouette—perfect for a first date.
If you don't yet own the editor and influencer-approved Mason pant, now's your sign to get a pair.
The shape, colour and texture make these loafers stand out, but they're still timeless enough to take you through many autumns (and dates) to come.
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