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The H! Fashion team’s go-to new season date night outfit


Consult and shop the H! Fashion team's date night outfits


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Orion Scott
Orion ScottStyle Editor
October 6, 2025
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Nothing beats a decadent date night ensemble, and though the colder months might invite a sense of unease due to the climate not playing ball, the H! Fashion team are here to take your hand and let you know it’s all going to be ok. 

Whether you’re in the early stages of a blossoming bond, meeting an acquaintance for the first time or celebrating multiple years of undying love, no matter your relationship status, a night out with your beau calls for a killer ensemble. 

Date night looks have forever been a favourite for those in the style sphere, as it’s an opportunity to dress up to the nines without feeling over the top. Sleek black slip dresses with a red lip and heels are always a go-to, just ask the likes of Maya Jama and Hailey Bieber. 

Though we’re never afraid to repeat a good outfit, here are our go-to new season date night outfit ideas that will be sure to have your partner weak at the knees. 

Molly Saunders outfit for datenight

Skirt, £79.00 at House of CB, Jacket, £895.00 at Marfa Stance, Shirt, £195.00 at Paloma Wool, Loafers, £350.00 at Miista, Bag, £85.00 at Charles & Keith

Je suis obsessed with this outfit. When pulling together an outfit for date night, comfort is above all. I'm not feeling 110% if I'm worried about how tight something is or how cold I am. Therefore, I'm opting for this Paloma Wool long sleeve; the sheerness of the fabric is cheeky, but I'm bearing no skin as the colder evenings dawn in. If I were taking this from an office day to night look, I'm layering it over a vest, so save HR the email. This gorgeous house of CB skirt brings the elegance and pairs perfectly with these plaid Miista loafers (loafers will be worn with a baby blue ribbed sock to harmoniously tie together all blue accents of this outfit). This Charles and Keith trapeze bag is just big enough for the essentials, so it will be my wing-woman of choice. I'm finishing this fit off with this gorgeous Marfa Stance parachute bomber; it's likely my date night will include at least a few drinks al fresco, so warmth is important, especially as we've just waved a very swift goodbye to the warm summer nights.

Clare Pennington datenight Outfit

Blouse, £40.00 at ASOS, Skirt, £215.00 at Selfridges, Bag, £475.00 at Strathberry, Tights, £21.00 at Heist, Shoes, £160.00 at Steve Madden

Being casually dressed isn’t something that comes naturally to me, so whether I’m going to a bowling alley or a Michelin-star restaurant, I’ll be wearing a mini skirt with an eye-wateringly high hem and platform heels. I tried to resist joining the burgundy brigade this year, but I have finally succumbed. It’s the perfect autumnal shade for those of us who are frankly allergic to wearing black, and looks lovely teamed with patterned tights and gold jewellery.

Aaliyah Harry Date Night outfit

Shoes, £517.00 at MyTheresa, Bag, £580.00 at Saint Laurent, Earrings, £30.00 at Saege, Dress, £390.00 at Kai

When it comes to date night, I often like to lean towards glamour. A dress that is comfortable yet chic is my go-to to make an impression. This Kai Collective halter neck midi dress with its unique leopard print design is a fun outfit for date night. I’m also a huge fan of a flirty feather accent, and the Marabou feather cape is stunning. Paired with a statement black clutch and court heels - it’s the perfect look. For a touch of luxury, add some gold jewellery to elevate the look even more.

Tania Leslau date night outfit

Jeans, £35.99 at Mango, Jacket, £900.00 at Selfridges, Bag, £280.00 at Vivienne Westwood, Top, £280.00 at Net-A-Porter, Shoes, £145.00 at Ballerette

Comfort is key when it comes to date night dressing, but you also have to feel confident. I feel best in dark-wash denim - and Mango offers long jeans for the taller lady, which is a major win in my book. Whimsical detailing is another go-to for me, so I’d team the subtly slouchy bottoms with a slinky lace-trimmed cami. To top it off? A hefty, butter-soft leather jacket to contrast the femininity of the top. Finally - a touch of metallic courtesy of Vivienne Westwood to match the chunky silver jewellery I’ll inevitably be adorning myself with before dashing out the door.

Orion Scott datenight outfit

Cotton Pyjamas, £109.00 at TBCo, Coat, £252.00 at JAKKE, Shoes, £137.00 at VIVAIA, Earrings, £60.00 at Essentiel Antwerp, Bag, £450.00 at Susan Fang.

For me, my ideal date night (and something I dream of most nights) involves two things - wine and bed. A pair of pyjamas so good they deserve to be seen is my bread and butter, so these TBCo options have me weak at the knees. I love a pop of colour, and before I return to my chambers after sitting outside under the lights, drinking wine at the Dalston Curve Gardens, a cosy coat that feels like you're being cuddled is pure bliss. As you can see, comfort is the theme of my ideal outfit; thus, a pair of satin ballerina flats is included. To spice things up and make sure people know wearing my pyjamas out of the house was a fashion decision, a collection of cute earrings and a beaded bag to store all the treats I'm taking home from the Tesco Express. 

Olivia Harper-Lower datenight outfit

Dress, £35.99 at ZARA, Tights, £50.00 at Harrods, Boots, £54.99 at H&M, Trench, £90.00 at M&S, Bag, £865.00 at Gucci

It may be dark and gloomy outside now that we’ve officially hit October, but selfishly, this means I can fully transition into autumnal dressing and, even better, autumnal date night dressing. This season, I'm leaning headfirst into the burgundy and brown tones because if not now, when? You can never go wrong with a pair of high kitten heel boots, and I'm adding a bit of fun by pairing them with a ruffle hem dress and the faux leather lacquered jacket that’s been on my wishlist for weeks. Plus, what’s date night without a bit of love? The mini heart-shaped bag is the perfect accessory not only for bringing in my burgundy tones but also for matching the ‘love is in the air’ vibe perfectly. 

Lauren Ramsay datenight outift

Shoes, £45.00 at ASOS, Jumper, £89.00 at M&S, Bag, £279.00 at Maje, Trousers, £198.00 at Reformation, Earrings, £145.00 at Selfridges

Unless it’s a super special occasion, my date night outfit follows a cosy-chic formula. I love a classic jumper in the autumn, and this Albaray piece in a beigey-brown palette feels super luxe while still effortless. The fashion week girlies have proven that silk has well and truly cemented its place in our wardrobes this season, and these trousers from Reformation are a cool-girl classic. Instead of jeans or plain trousers, they instantly elevate an outfit, but still deliver the same comfort. A simple suede ballet flat, a fun bag and chunky gold earrings are the perfect accessories to tie everything together - easy, elegant, and just the right amount of understated glamour.

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