I've Found 20 Cute Outfits for Every Occasion, From Work to Going Out

Whenever you feel like you're short on fresh, fun outfit ideas, what's the first thing you typically tend to do? Paging through magazines is one great way to get inspired, as is searching through street style pictures. But perhaps the easiest, most readily available place to look for unique ensembles that are sure to get your creative juices flowing is on Instagram. Yep, we've said it before, and we'll keep saying it: The photo-sharing app is a treasure trove of fashion inspiration, and so it's exactly where I began when hunting down cute outfit ideas for every occasion in your calendar.

Whether you want an elegant look for a night on the town with friends or something that's a bit more out-of-the-box when it comes to your office attire, these outfits all easy to re-create. Keep scrolling to see the ensembles we'll be copying from fashion insiders, and shop the key pieces needed to replicate each for yourself.


(Image credit: @thestylistandthewardrobe)



(Image credit: @livvperez)

Style Notes: Dressing for the office doesn't have to mean an all-black suit. Embrace the seasonal shades of autumn with cosy knits and practical corduroy in a refined colour palette of greens, browns and neutrals. 


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Style Notes: Try swapping the cotton shirt you wore all summer for something a little more substantial like leather. Not only does its glossy finish always look expensive, but it'll serve you well once the temperatures drop. 


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Style Notes: Wondering how to tackle a smart-casual office dress code? Try a leather blazer and wide-leg jeans. The combination of sharp tailoring on top and a loose, comfortable fit on the bottom ticks both boxes. 


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Style Notes: Yes, you can wear miniskirts in the office too, and my favourite combination is a retro-inspired look. Just add knee-high boots, a wide collar and a longline coat and channel the best of the late '60s and early '70s. 


(Image credit: @thestylistandthewardrobe)

Style Notes: Put a modern spin on the traditional three-piece suit by mixing colours, prints and fit. As Joanne Hegarty proves, the perfect accompaniment to a cropped waistcoat are clashing wide-leg trousers, the easiest way to make pinstripes feel a little less stuffy. 



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Style Notes: The countdown to the end of bare-leg season is in sight, so make the most of some of the milder weather by wearing your mini with a wool coat and polished loafers. 


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Style Notes: Cheers to the weekend, and if your plans include getting dressed up and heading out, consider an animal-print dress, which requires minimal effort and always yields maximum impact. This summer reaffirmed our love for leopard and zebra print in particular, and we aren't ready to hang up our spots and stripes quite yet. Make it feel seasonally appropriate by opting for a long-sleeve midi dress and add over-the-knee boots for day and platform heels for the evening. It's time to go wild. 


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Style Notes: The weekend is for relaxing too, and if you're heading to the shops, running errands or holding down the fort, you need an outfit that's easy to throw on but looks good too. Go for a high/low combination of a casual crew-neck with a dressier midi skirt, and hey presto, you've got yourself the ideal outfit to wear with trainers. 


(Image credit: @rayan.xasan)

Style Notes: Rayan Xasan's look has autumn written all over it, and the best thing about this look (other than the attention to detail) is the unexpected colour combination. We might not have thought of it before, but somehow buttery yellow and strong, inky navy just make sense.



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Style Notes: When we say we're wearing jeans and a nice top, this is exactly what we mean. This failsafe outfit formula is a classic for a reason, and whether you're heading out to a party or an intimate dinner for two, sparkles and denim are always a guaranteed winner. 


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Style Notes: Okay, it's not a look for the fainthearted, but as our editor group chat pored over yet another new pic of a celeb in a sheer dress, we had to admit we were onto a certified trend. The naked dress is having a moment, but if you'd like to leave a little more to the imagination, layer a fine-knit dress over a black slip, and add killer heels to up the ante. 


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Style Notes: And speaking of controversial evening looks, this is a trend that's sure to ruffle a few feathers. Tops, dresses, jumpers, even jackets are adorned with plenty of feathers this season, and I love Ali Tate Cutler's minimalist approach to such high-octane glamour. With an off-the-shoulder fit, thigh-high split and, of course, plenty of faux feathers, this look doesn't need to be over-accessorised to let the outfit do the talking. 



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Style Notes: When it comes to travelling, the best advice is always the same. Pack light, and think comfort first. If you've booked a staycation or are in search of some winter sun, you'll still need clothes with a relaxed fit to the make the journey that much easier, and what could be more comfortable than an oversized knit and flat shoes? 


(Image credit: @monikh)

Style Notes: I think I might be allergic to jumpsuits, as no matter where I try them on, the fit is always terrible on me. One thing I can rely on, however, is the boiler suit. Baggy, laid-back and quite literally an entire outfit in one piece, the boiler suit is perfect for the busy traveller who needs to focus on their itinerary first, fashion second. 


(Image credit: @monamali_ )

Style Notes: Autumn is all about clever layering, as the weather can change in an instant, so be prepared for both the warm and the cold by wearing a heavier denim jacket under a light cotton trench. You can easily take one off to carry it while the sun is out, and once the sun sets, you've got an extra layer ready to go at a moment's notice. 


(Image credit: @lucywilliams02 )

Style Notes: I've been looking for a new way to make trainers feel fresh again, and as it turns out, you only need a few pieces. One, a trusty trench. Two, a bold knit. And three, graphic trainers that will go with everything from denim to dresses. 



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Style Notes: Thankfully for us, leggings are no longer relegated to the gym floor, and if you spent the last year reacclimatising from leisurewear, allow me to lure you back in with a look that manages to be comfy and chic. Marianne Smyth is a master of making casual cool, and this coat/cashmere/legging combo is exactly what you'll want to wear on your way to working out. 


(Image credit: @monikh)

Style Notes: What you actually wear in the gym has to serve a purpose, and whether you're boxing up a storm or stretching out in Pilates, look for breathable fabrics, plenty of stretch and maximum flexibility. 


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Style Notes: And breathe. Ease your way through the post-gym cooldown with loose layers and practical accessories. The jumper you wore to the gym is probably now best shoulder-robed, and if you've sweated out your hair, no problem, there's a cap for that. Even better if it happens to be designer. 


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Style Notes: If your style happens to be a little more glamorous than gym buff, there's a leisurewear look for you too. Pair statement faux fur with loose-fitting joggers should the mood to power-walk suddenly decide to take you. Otherwise, this outfit will look equally good sat outside of a restaurant. It's all self-care after all. 

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Remy Farrell
Fashion Editor

Remy Farrell is a London-based shopping editor with nearly 10 years of editorial experience covering fashion, beauty and lifestyle. After graduating with a journalism degree and working on the editorial and fashion teams for titles such as Grazia, Elle, Cosmopolitan and British Vogue, she moved into the luxury e-commerce sector, working as fashion assistant at TheOutnet.com styling for the social media channels and helping to develop the collections for the in-house brand Iris & Ink. After expanding an assisting and styling portfolio that includes shooting talent such as Gigi Hadid, Victoria Beckham and Miquita Oliver, she also branched out into beauty, creating tried-and-tested reviews and diverse beauty content.In her role as shopping editor at Who What Wear, Remy is interested in discovering new and exciting brands to share with the Who What Wear readership and particularly loves uncovering hidden gems at affordable prices to make shopping accessible to everyone.Born and raised in Sheffield, Yorkshire, Remy moved to London in 2014 and lives in the Docklands with her partner and pug Billie.