How Stylish Women Dress Cool and Casual in 2025
Words by Eleanor Hibberd
For the sartorially motivated, deciding what to wear in your downtime can feel unexpectedly challenging. How do you dress casually without your outfit feeling uninspired? The good news is that there’s never been a better time for everyday fashion. An effortlessly cool aesthetic has been gaining traction on the runway over the latest seasons, culminating with a slew of informal wardrobe foundations leading the charge for Spring/Summer 2025, from checked flannel shirts at The Row to versatile neutrals at Rick Owens, Lemaire and more.
But how to get it right off the runway? You need only look to fashion’s most photographed women, for whom every trip beyond the doorstep is snap-worthy. As worn by tastemakers from Alexa Chung to Hailey Bieber, these five key pieces are the pillars of a cool-casual wardrobe. Running errands has never looked so good.
1. Trench Coats
Trench coats achieve a kind of chic nonchalance unrivalled by any other item of clothing – classy yet undone, timeless yet current, considered yet effortless. Cut is everything: the best street stylers steer clear of anything too stiff and fitted, opting instead for unstructured pieces worn loose and open to maintain their casual edge. Look to Jennifer Lawrence, for example, whose menswear-inspired trench coat from The Row captivated the internet when she donned it out and about in New York last year.
2. Oversized Shirting
If you’re stepping out on a mild day, there are few things you could reach for that would tick as many boxes as a simple button-up. Comfortable and effortlessly cool, a shirt strikes the perfect balance of smart and undone, and pairs with anything from wide-leg trousers to jeans and summer shorts. The trick is to make it look like it’s been swiped from a gent’s wardrobe (in fact, our Menswear department on the Second Floor is never a bad place to start). Worn untucked for weekends, an oversized fit is paramount to the casual-cool aesthetic, as Kendall Jenner and Alexa Chung will attest.
3. Baggy Jeans
Denim may be a staple for casual days – but it’s no secret that the right cut can make or break a look. If Hailey Bieber’s wardrobe is any indication, baggy jeans are the It-girl’s single most valuable wardrobe investment right now. While skinny jeans await a revival and ankle-length ‘mom’ shapes take a backseat, looser silhouettes with ‘puddle hems’ made their presence known via ’90s straight legs, ultra-baggy and horseshoe shapes on the Spring/Summer 2025 runways.
4. Leather Jackets
Much can be said of the staying power of leather jackets. You need only shrug on one of these sartorial icons to up the cool points of your outfit – a dreamy scenario when all you want to wear is a T-shirt and jeans. Today, the fit is boxy and retro, with tidy point-collar styles trending alongside bomber shapes, shackets and aged-leather effects. Purists, look to Anine Bing and Prada for your quintessential biker jacket – they never miss.
5. Cosy Cardigans
We’ve got TikTok to thank for the prevalence of ‘coastal Grandma’, ‘eclectic Grandpa’ and ‘dark academia’ as terms in current fashion discourse – aesthetics that, at their core, are ultimately about good knitwear. New York brand Khaite has been flying the flag for elevated cardigans for years, with its signature Scarlet style going viral in 2019 when Katie Holmes wore it with the matching cashmere bralet. Today, Gigi Hadid backs the trend too, with her brand Guest in Residence stocking a colourful plethora of layering staples. Whatever aesthetic you subscribe to, consider it a pillar of your casual wardrobe.
Added Extras
Attention must always be given to accessories, even when playing it casual. The ‘incognito A-lister’ look has inadvertently made baseball caps a street-style staple – alongside a great pair of sunglasses. Bags are all about sizeable slouch in 2024. Overspilling with belongings, Bottega Veneta’s Hop and Loewe’s Puzzle Fold say: I’m running errands, and I look good doing it. On your feet, ballet flats and preppy loafers keep low-key ensembles grounded – because who wants to wear heels on their day off?
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