I've Analysed It—These 6 Pieces Are Timeless and Can Be Worn Year-Round

This summer, each day we're surprised at the weather, as there's simply no guessing what will happen. Though it's sunny today, all too soon, the forecast will change, and that’s why I’m drawing my attention to familiar territory: transitional dressing. The typical British outlook is wet and dreary with intermittent bursts of warmth that we are seldom prepared for, so pieces that can be worn throughout the seasons are crucial when building a hard-working wardrobe.

Ever since I started mindfully curating my own wardrobe, I honed in on key items that can be mixed and matched. That whittled down the cost-per-wear of my clothing significantly, and when it’s time for the seasonal switchover, these are some pieces that have permanent residence in my wardrobe.


(Image credit: @jessicaskye)

Although I’m a girly dresser, a vast proportion of my wardrobe consists of simple, trans-seasonal items that may appear like basics but offer up plenty of styling options. A simple shirt, for example, can be completely reworked depending on the time of year. It can be made formal with tailoring or tucked into a miniskirt and worn with canvas trainers for an off-duty look. That same shirt can be knotted at the waist or worn open as a beach cover-up. I also consider some less typical pieces for transitional dressing—knitted dresses, chunky sandals and linen skirts are prime examples of this. Although linen is inherently a summer fabric, I always wear it through autumn with chunky knits. And while closed-toe styles are needed during the winter, there is a sweet spot on the periphery of summer when chunky sandals and open-back loafers can be worn.

Below, I’ve chosen some of my favourite transitional pieces for the months ahead including some trend favourites for 2023 that fit seamlessly into my pre-existing collection. Keep on reading to see the many ways you can style six transitional basics from spring to winter.

1. A Knitted Dress

Spring/Summer: Knitted Maxi With Sandals and a Leather Basket Bag


(Image credit: @monikh)

Knitted dresses are so easy to style no matter the weather. Right now add minimalist sandals and a large basket bag to complete a summer look. 

Autumn/Winter: Knitted Dress With a Silk Head Wrap and Chunky Boots


(Image credit: @femmeblk)

I wear knitted dresses throughout all seasons. Simply add a bag and jewellery, and you have the simplest but chicest of looks that you can wear any time of the day.

2. White Shirt

Spring/Summer: White Shirt and Shorts With Fisherman Sandals


(Image credit: @bubblyaquarius)

The white shirt is a fabulous component of a capsule wardrobe purely because you can build so many looks around it. The addition of shorts and fisherman sandals makes this the perfect ensemble for summer days in the city. This look further highlights the transitional dressing component with the hardwearing footwear. Add a belt to tie in the brown accents.

Autumn/Winter: White Shirt, Ecru Jeans and Tan Clogs


(Image credit: @astyleedit)

Light-wash looks work best with varied shades like this white and ecru ensemble. Paired with tan accessories and the infamous Birkenstock clogs, it turns a precious look into something a little more attainable for day-to-day wear.

3. Denim Skirt

Spring/Summer: White Shirt and Denim Skirt With Suede Mules


(Image credit: @sylviemus_)

Tuck the white shirt into a denim midi skirt, and prop the look up with mules. This is a classic Parisian style that you can always fall back on in the spring and summer. You can also transition this look into autumn by throwing a trench coat on and a knit over your shoulder.

Autumn/Winter: Belted Blazer With a Denim Skirt, Tights and Heels


(Image credit: Getty Images)

Same skirt, different season! With an oversized belted blazer, sharp-collared shirt, tights and slingbacks, Sylvie brings an '80s-workwear lilt to her classic denim skirt, and it works.

4. Linen Skirt

Spring/Summer: Cropped Tank Top With Linen Midi Skirt and Slides


(Image credit: @lindseyholland)

Lindsey pairs a linen skirt with chunky sandals and a cropped vest. It’s the perfect marrying of girly and androgyny. 

Autumn/Winter: Oversized Knitwear With Linen Maxi Skirt 


(Image credit: @monikh)

Monikh shows that you don’t have to leave summery textiles behind in autumn. Instead, celebrate them. Wear your chunky wool knits with netted fabrics like linen and cotton instead of burying them away.

5. Voluminous White Maxi Skirt

Spring/Summer: Tank Top With White Voluminous Skirt


(Image credit: @brittanybathgate)

Here, Brittany embraces bohemian styling with a laced choker and windswept hair. Her full maxi skirt which may otherwise look formal has a nonchalant and breezy appeal, due to the clever top-half pairing.

Autumn/Winter: Cardigan With White Voluminous Skirt


(Image credit: @marina_torres)

Marina shows how you can transition what you'd consider a 'typical' summer style into something cool weather appropriate. Simply add a cardigan and trainers and you can squeeze ample wear out of your cotton skirts.

6. The Black Midi Dress

Spring/Summer: Black Midi Dress With Slip-on Sandals


(Image credit: @lizzyhadfield)

This styling shows us simplicity speaks volumes. The cleverly crafted neckline is detail enough, so apply accessories to your desired effect. When autumn arrives you can pop a long sleeve top underneath or assign it for eveningwear with an oversized blazer over the top.

Autumn/Winter: Black Midi Dress With Chunky Loafers


(Image credit: @emmarosestyle)

This Totême number is a transitional dress at its finest. The high neck is enough coverage for a windy day but swap out the loafers for sandals and the oversized bag for a jute bag in the height of summer.

Up Next: Autumn Is Coming—12 Simple Items You Won't Want to be Without

This post was originally published at an earlier date and has since been updated.

Freelance Fashion Editor

Avalon Afriyie is a freelance writer and storyteller based in London. She specialises in sustainable fashion, health and the narratives of marginalised communities. She has a background in fashion show production and styling, having previously worked on The Clothes Show and with the Lyst Group. Since graduating in 2013 with a BA (Hons) in English and contemporary media, she’s worked as a feature writer for an independent publication and a contributor for Quill’s creator network. She now marries her passion for words and style, writing for some of the most esteemed fashion and lifestyle publications, Who What Wear UK and Stylist. Avalon also provides copywriting services, creative consultancy, and visual media for independent businesses, including travel guides, interviews, press releases and blog posts. Her work has been featured on Lush, Contiki, Youswim and Ohne. She spends her days writing to her heart’s content for business and pleasure, shooting on film and dreaming of residing a stone’s throw away from the ocean with her love and a pup (clad in a sweeping frock, of course). She’s currently penning ideas for a book of personal essays and free verse poetry on love, life and the stages in between.