15 Fashion Tricks to Master When Transitioning From Sunny to Rainy Weather

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The only thing more fickle than fashion is the weather. In a season when it’s scorching hot one minute then torrential the next, every day can be a sartorial adventure. With summer on its last glorious leg, and the rainy monsoon season waxing and waning its way in, outfits need to be appropriate for both climates. The key to nailing this awkward in-between phase is balance, in both color and proportion. A feisty summer dress paired with a classic trench, for example, simultaneously channels insouciance while championing practicality. Weightier outerwear, when rendered in sorbet hues, looks instantly light and fresh. Fickle atmospheric conditions can even work in one’s favor, with both spring and autumn pieces open to appropriation. With some clever styling, looking chic is sure to be a breeze, wherever the barometer arrow points.

1. Find fresh new ways to style structured blazers.

Sharp with its crisp lines and power dressing vibe, a blazer lends instant polish to any outfit. It's a great way to shift your summer looks into fall, adding much-needed structure to flimsier fare. Pair it with a slinky bias-cut slip, or cop the look of many a model-off-duty by wearing it with distressed jeans and statement tees. It also makes quite an impression paired with skirts, creating an almost mismatched skirt suit of sorts. Just as perfect in the boardroom as it is on the boardwalk, this versatile piece is sure to get you a lot of mileage.

2. Lounge in this season’s cropped pants and relaxed silhouettes.


There’s nothing quite as bothersome as trouser hems getting wet while being dragged through the rain. Thankfully, this season’s pants come a little cropped, whose abbreviated lengths incidentally also keep us cool when the temperatures rise. Cut right at the ankle or artfully cuffed to almost mid-calf, this relaxed take on tailoring is a breath of fresh air. Pair them with languid menswear and you get a look of irreverent androgyny, but wear them with barely-there tops and you get a whole new take on the femme fatale. Finish with sleek heels or of-the-moment mules and you’re all set.

3. Keep your LBD on constant rotation.

Proving that it truly is one of fashion’s greatest inventions, the LBD is one piece that effortlessly transforms with a simple change of accessories. While traditionally a go-to for cocktail hour, this stylish chameleon can easily be chic brunch-wear too when paired with earthy accents, and casual, cool girl hair. Armed with killer stilettos and wine-stained lips, however, and it's back in business for a memorable night on the town. When you really don’t know what to expect, it’s great to have such a simple, yet versatile ally on your side.

4. Own the season in a chic trench.

The flexibility of this outerwear classic has never been in question but is even more evident now that the weather has become quite unpredictable. Buttoned up, it keeps the wearer cozy and warm, while left open, it frames one’s outfit with aplomb. Absolutely sophisticated in neutrals like camel, moss green, and gray, we’re also loving it rendered in fashion-forward colors and prints. Matching anything under the sun or rain—from a demure day dress to skinny jeans—it’s the must-have hero piece of transitional fashion.

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5. Exude sophistication in opulent spice hues.

There’s nothing like dreams of exotic locales to banish the gloominess of inclement weather. And while a trip to Marrakech may not be imminent, indulge your sartorial wanderlust in the in rich spice hues of saffron, turmeric, paprika, and the like. Saturated and warm, these directional tints give the eye that much-needed pop of color. Rendered in languid dresses that show just the right amount of skin, these luxurious and escapist mid-tones are a great way to segue into moodier fall fashions.

6. Pair your summer skirt with a fall-winter top.

Extend the life of a flirty, floaty skirt by pairing it with more covered up tops such as a crisp button-down shirt, or a long-sleeved blouse. It’s the perfect way to keep a little bit of summer alive while still being appropriately dressed for these rainier times.

7. Indulge in midi dresses. 

If you’re obsessed with demure tea dresses, then you’re in good company. It’s a sophisticated silhouette that’s been seen on both ladies who lunch and the ladies of royalty, and is the perfect frock to live in during these transitional times. It's long enough to be appropriate for brisk weather, while in the floatier fabrications, work just as well when it's balmy. Interesting print combinations, inventive drapes, deep necklines, and mid-thigh slits are giving this classic number a new lease on life. With just the right amount of femininity and flair, you’re sure to keep these dresses in constant rotation.


8. Have fun with sheer outerwear.

Lace jackets and sheer coats are the perfect way to cover up while still letting a little bit of the sunshine in. They’re great for days when it’s only just a wee bit chilly, and are an amazing way to add layers without adding bulk. Marrying summery fabrics with classic winter shapes, these decadent pieces let you hold on to the last glorious vestiges of summer with dreamy, redolent ease. 

9. Whip out your favorite white sneakers.

It’s the unlikely style piece that has gotten a lot of traction lately, getting nods of approval from celebrities, models and street style stars alike. Worn with a sense of sartorial irony, fashionistas are pairing this sporty staple with ladylike ensembles to great effect and are getting away with the most creative combinations. Exuding the coolness and comfort that is the heart of athleisure, they look fresh when the sun’s out, but will keep toes away from puddles with the rains come. 

10. Style your summer dresses with longline cardigans and coats.

Your favorite summer dresses need not be shelved when it starts to drizzle. Continue to wear these vibrant pieces well into the cooler months by topping them off with cozy jackets and cardigans. When mixing and matching pieces, aim for contrast. Capricious spring fabrics like crepe, poplin, or chiffon look amazing when layered with light knits. Cinch at the waist to show off your figure, and you’re good to go.

11. Fall in love with autumn florals.

Botanical prints may feel counterintuitive after the dog days of summer have passed, but they can be just as desirable when rendered in moody palettes and sensual fabrics. Exuding a dark femininity, they ease us into fall with an air of decadence and a layer of mystery. Appearing in languid silk dresses, body-hugging sheaths, or sheer blouses, they give us just the right amount of romance, with of course a little bite.

12. Liven up your look with colorful outerwear.

When you’re not quite ready for autumn’s somber palette, opt for coverups rendered in vibrant hues or look-at-me prints. They make any outfit instantly interesting with their boldness, and are a great way to show off one’s personal style. When you need to make a memorable first impression, then a photogenic coat is the way to go.

13. Dress up in a lot of light layers.

Top off your silk camisole with a light sweater and then drape a statement jacket over it. Or layer a thin knit top under your favorite slip and add on your fave trench. When it can be multiple temperatures in one day, it’s best to be prepared. The key is, of course, to keep layers light, both to streamline the silhouette and to keep it from being too warm for our tropical clime.

14. Swap boring jackets for a statement-making kimono.

No longer relegated to just the bedroom, fashion’s love affair with sleepwear-inspired pieces continues right into the next season. Top off everyday jeans and tanks with a printed kimono or a satiny boudoir-esque robe, for looks that are breezy enough to be worn in the summer but with just the right amount of coverage for when the temperature drops.


15. Experiment with shapes and proportions

There are pieces in your closet that you never thought would work together but somehow do. Like that lacey bralette that you thought would be too much, but somehow shows just the right amount of skin under a light blazer. It’s the little surprises that make fashion all the more fun, and what better way to make a firm style statement than by taking a few risks.

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Mariane Perez
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