Winter date-night outfit inspiration for Valentine's Day and beyond
Whether you're 10 years deep into your relationship or dipping your toe back into the dating pool, finding an appropriate date-night outfit can pose just as much of a dilemma as choosing the ideal activity, location, and in some cases, your date for the evening.
Silver screen depictions often cite the a little black dress as the perfect date-night ensemble, and although a form-fitting piece absolutely has its place, date-night isn't a one size fits all approach to dressing.
When in doubt, take cues from the setting to form the beginnings of your outfit. It's smart to consider your journey to and from – as confident as you might feel in a heel, you'll feel infinitely less so after having to walk for miles just to get to your location. Starting with your shoes can also help to clear any styling-induced mind block; a knee-high boot is a date-night classic, offering optional height with a versatile design. Alternatively, keep it casual with a pair of chunky loafers or ballet flats which you can dress up or down depending on the mood of the evening.
Below, we've compiled our edit of the best date-night outfits which will help to ensure that romance is on the menu.
The best winter date-night outfits 2025
Ladylike silhouettes
We're forever in awe of Kelly Rutherford's effortlessly elegant looks, so it's no surprise we're taking a style cue from the actress for a sophisticated date night. Whether you're heading to an upscale cocktail bar or a Michelin star restaurant, this feminine silhouette is the perfect accompaniment – we love the structured strapless bustier for showing off your décolletage with a demure approach.
Róhe strapless bustier
Róhe recycled wool-blend felt midi skirt
Miu MIu Wander mini hobo bag
The Row Vika knot satin mules
The white suit
A beautifully tailored white suit can be wheeled out for date night time and time again. The styling options are limitless; opt for a sheer blouse for a full lean into romance, or a black turtleneck for a more sophisticated ensemble. For something more casual, a pair of ballet flats or loafers will bring a touch of Parisian laissez-faire, while a pair of classic court heels heels will elevate the look for a fancier occasion.
Saint Laurent tie-neck silk chiffon blouse
Wardrobe.NYC contour double-breasted wool blazer
Wardrobe.NYC low-rise wool pants
Jimmy Choo Isa 95
The suede style
If your evening plans call for a more off-duty approach, a suede jacket provides an easy elegance that can translate as well to your local pub as it can to a music gig. Style with a white T-shirt, black straight-leg or slightly flared trousers and a pair of kitten-heeled ankle boots, matching your bag to your jacket for a cohesive outfit.
Mango leather jacket
Rag & Bone round neck cotton-jersey T-shirt
Bottega Veneta straight-leg high-rise woven jersey trousers
Alaïa Le Teckel suede tote bag
Gold accents
Muted neutrals and soft beige dresses can deliver on refined style when paired with the right pieces. Our tip: incorporate gold jewellery into your outfit, opting for chunky, statement pieces that contrast the minimalism of a neutral-hued dress. This simple styling rule works with every style, from slinky slips to form-hugging sculptural pieces and sleek column dresses. Finish with some shearling outerwear or a long wool coat and a pair of knee-high boots to ground the look.
Issey Miyake pleats please maxi dress
Staud Wally boots
Monica Vinader x Kate Young 18ct gold-plated bangle
Lapillus Drop Earrings 14kt Gold Vermeil
The fancy pants
Date night is all about having fun, so why not use the excuse to embrace a little whimsy in your outfit? Let a pair of statement trousers like Daily Sleeper's feather-trimmed style do all the talking, and contrast on your top half with a structured blazer, doubling down on elegance with a pair of slingback heels.
The Frankie Shop Bea crepe blazer
£305.00 at net-a-porter.com.uk
Sleeper feather detail pajama set
Toteme T-Lock leather shoulder bag
£1100.00 at net-a-porter.com.uk
Notabene Elisa slingback pumps
Courting crimson
Red is undoubtedly the ruling colour of romance, but if a head-to-toe claret ensemble seems dramatic, a statement scarlet coat can deliver a more nonchalant nod to love. Keep the rest of your outfit either black or white; tailored or leather trousers with a black turtleneck makes for a refined look, or opt for a white vest top for more low-key evening plans.
Simone Burgundy Vinyl Coat
Nanushka semi-sheer merino knit top
Toteme mid-rise leather straight pants
Amina Muaddi Barbara 90 leather boots
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