I Can Tell You're a Fashion Person If You're Wearing One of These Outfits This May
I've collated seven easy but elegant outfit ideas to help you get dressed this May. Keep scrolling to see and shop the outfits perfect for a sunny spring.
Finally, a new month! After April's inclement weather, there's nothing but picturesque blue skies and 24-degree days on the horizon for May, making this the perfect time to transition from a cold-weather wardrobe to a semi-sunny one.
After months of enviously scrolling through warm-weather pics on Instagram, longer, sunnier days are almost within our grasp. However, dressing in May is still all about transitional pieces (because, as much as we wishfully think, summer isn’t here just yet). So, the simplest and smartest way to achieve a chic ensemble every day this month? A steady run of mix-and-match staples you can layer up (or down) as you need.
From the basic dresses that every wardrobe should have to the nostalgic ‘90s skirt taking over this spring, I’ve assembled seven looks that take the guesswork out of what to wear in May. Trust me: each of these pieces is a well-placed addition that will serve your capsule wardrobe this spring and next. Scroll to see them, and of course, you can shop them here too.
7 Easy But Elegant Outfits I've Bookmarked for May 2026
1. Halterneck Blouse + Silk Trousers + Denim Jacket
Style Notes: Simple yet impossibly chic satin trousers have been having a moment for a while now, with no signs of slowing in popularity this spring. To make them feel more current, take cues from sophisticated French women and style them with a draped halterneck top, denim jacket (in case you need some warmth) and sleek thong sandals.
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Zip it up to show off the funnel-neck silhouette.
The styling possibilities are endless.
You can also style these with ballet flats and a striped shirt this spring.
These look a lot like several much more expensive designer pairs.
An icon.
2. Embroidered Dress + Clogs + Raffia Bag
Style Notes: Dress season is here, but before I style them with my strappy sandals and basket bag, I’ll be following Sara Walker's lead and opting for a broderie style, finished with a pair of fashion-forward clogs and a raffia tote on warmer days. It's a fail-safe way to add a point of difference to your simple dress looks.
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The embroidery! The delicate buttons! This dress feels like spring personified.
A French girl's dream.
PSA: Its time to invest in an elevated raffia bag before they all sell out this year.
These sunglasses are the perfect finishing touch to everything from dresses to jeans and linen two-pieces this spring.
A classic.
3. Trench Coat + Bootcut Jeans + V-Neck Jumper
Style Notes: The change of season doesn't mean your style needs to get overly fussy. Take Sofia Boman's look, for example. By opting for light-blue bootcut jeans and an ecru trench, her pared-back layers feel far more spring-focused.
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So many of my favourite fashion people own The Frankie Shop's Riva in this fresh ecru shade.
Layer this over a white T-shirt as Sofia has, and then tie it around your waist when the day gets warmer.
A Who What Wear UK fashion-editor favourite.
Thanks to the stretch denim, these are some of the comfiest bootcut jeans on the market right now.
The angular heel and sleek pointed-toe finish makes these boots feel far more current.
4. Scarf Top + Knee-Length Skirt + Slingback Kitten Heels
Style Notes: When we no longer need to layer for the sake of warmth, a new realm of styling opportunities opens up, and in spring 2026, scarf tops have never been more popular. Adding sophisticated polish to your look, there’s a decidedly '90s feel to this style that fashion people love. Lean into its nostalgic vibe and finish with a floaty knee-length skirt and sleek slingback kitten heels.
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Scarf tops have been all over my social media feeds of late.
This is very Carolyn Bessette Kennedy-coded.
Charles and Keith shoes are a fashion person's best kept secret.
Hardly Ever Worn It has a rigorous authentication process, so you can trust that this Chanel Flap Bag is the real deal.
Tortoiseshell sunglasses will never date.
5. Trench + Capri Trousers + Thong Sandal
Style Notes: You'll be hard-pressed to find a spring jacket that works quite as hard as a trench coat. Timeless and most importantly functional, it'll keep you warm on cooler days and chilly nights. Keeping her base simple, Nina Lea Jolley plays with colour and trending styles like capri leggings to keep her look feeling fresh.
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Personally, I'll be swapping Nina's sweeping trench for this chic mid-length iteration instead.
Kendall Jenner and Hailey Bieber both own this pretty pointelle tee from Cou Cou.
This is exactly how I plan on dressing this spring.
A pair of black elevated flip-flops will serve your wardrobe well for years.
Dopamine dressing made easy.
6. Blouse + Flared Jeans + Mary Janes
Style Notes: In spring 2026, fashion people can't seem to get enough of romantic blouses in crisp cotton and breathable linen. Whether dressed up with a poplin skirt or made more casual with jeans, they're a perfect way to bring life into an outfit whilst remaining well within the comfort zone of minimalists.
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The perfect additional layer, this & Other Stories knit looks almost identical to the viral Khaite Scarlet cardigan.
Take it from me: Dôen makes some of the best blouses money can buy.
The ankle-grazing raw hem elevates this pair of high-waisted, wide-leg jeans.
Loewe's Bracelet Pouch can be worn on the shoulder or cuffed around the wrist.
I'm so glad espadrille Mary Janes are back.
7. Jumper + Midi Skirt + Sandals
Style Notes: Thanks to CBK, hip-skimming midi skirts have never been more popular. To give the timeless shape an updated feel, pair it with a fitted black jumper layered over a white T-shirt and finish with an unexpected wedge thong heel.
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Wear layered or tied around your waist.
A slim white top is so versatile and will never date.
The perfect '90s white skirt.
The addition of a functional wedge elevates this pair of thong sandals.
The Freja New York Jane bag is high up on my wish list.
