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.

Best Transitional Basics: @jessicaskye wears Baserange shaw dress and Dune sandals



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

Best Transitional Basics: @monikh wears Baserange dress



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. 

The knit dress is a piece you can squeeze lots of wear out of everywhere for all seasons and all occasions. For day time add trainers or sandals, or elevate for evening with a sleek mule.

My Dragon Diffusion bag has been one of the most sensible wardrobe investments. I wear it come rain or shine and the patina continues to age beautifully.

Ancient Greek can do no wrong in my eyes. They master sandals so well.

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

Best Transitional Basics: @femmeblk wears Dior saddle handbag with black knitted dress



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.

This dress blows all transitional items out of the water. Wear it with anything from trainers to chunky boots and heeled pumps.

Crescent-shaped bags have a classic appeal and the gold hardware adds to the allure.

I didn't think I was a chunky-footwear girl until I purchased a pair a few years ago. Now, they’ve become a key piece in my footwear capsule.

Wear the stars close to your heart with this Grecian-inspired necklace. It’s guaranteed to bring sparkle to any outfit.

A classic scarf is a staple in my accessory wardrobe. Wear this as a hair tie, bag accessory or neckerchief.

2. White Shirt

Spring/Summer: White Shirt and Shorts With Fisherman Sandals

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.

With Nothing Underneath craft forever shirts inspired by British heritage.

The mom fit offers more coverage if you don’t like your shorts too short.

Years on and the Loewe basket bag still reigns supreme!

Fisherman sandals are a transitional item on their own—open enough for warm weather yet closed enough for when the heavens (inevitably) open. It is the UK, after all.

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

Best Transitional Basics: @astyleedit wears Birkinstock Boston clogs



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.

The oversized silhouette is pure perfection. 

Ecru is the new black and Lee have a host of considered cuts available in an inclusive size range.

The craftsmanship of Strathberry bags is exquisite. Each bag comes complete with a unique metal detail.

Birkenstock Boston clogs are the pared-back footwear staple for all year round. 

3. Denim Skirt

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

Best Transitional Basics: @sylviemus_ wears classic white shirt and denim midi skirt



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.

No one ever regrets investing in a crisp white shirt. The wide cuff feature makes this one extra snazzy.

I've seen a fair few denim skirts and this one ticks the boxes on silhouette and length. It also comes in a range of sizes.

Pointed mules might be hit or miss, but there's no denying how chic this Vagabond pair is.

You'd never believe this sculptural bag was from the high street. 

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


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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.

This Arket blazer is universally accepted as the best tailored jacket on the high street.

Swedish Stockings are the place to visit if you're looking for high quality and sustainable hoisery.

This longer hemline makes for a more modern silhouette than the denim skirts that were popular in the noughties. I can also attest to the quality as I own this!

Slingbacks have become part of my footwear capsule and my favourite style of shoe. This is a pair you'll wear on repeat (I particularly like the ruched detailing)

4. Linen Skirt

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

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

If you’ve had enough of bunching excess fabric into bottoms, opt for a cropped tank top for a seamless fit. Come winter, it’s an additional layer under knitwear, and you can even wear it over a shirt!

Honestly, I've never met a linen skirt I didn't like and Dissh is the retailer I think of whenever I'm in need of a timeless linen design. This piece ticks all of the boxes on quality and fit and if it's like any of my other pieces from there, it'll last for years.

Dear Frances never put a foot wrong. Whether I’m looking for a dainty pair of heels or grungy flatforms, it’s my first port of call for considered footwear.

Autumn/Winter: Oversized Knitwear With Linen Maxi Skirt 

Best Transitional Basics: @monikh wears Prada linen skirt and Toteme Jumper



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.

Navy Grey's relaxed knit is back in stock and it was certainly worth the wait. It's soft to the touch and in a hue that goes with almost everything.

Understated and timeless. A piece you'll wear forever.

When I think of chunky flip-flops The Row is the first brand that comes to mind. The Ginza shoe will continue to look chic with autumn looks if the weather permits. 

The noughties clutch had a makeover - a plump, squishier variation. 

5. Voluminous White Maxi Skirt

Spring/Summer: Tank Top With White Voluminous Skirt

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.

You'll never regret investing in good quality basics. I've had basics from Arket that are still in pristine condition years on.

The white midi skirt is having a moment and as a lover of full skirting, I'm certainly not complaining. This A-line offering by Reformation is one of the nicest styles I've seen. It falls at a great length and features pockets!

Heart-adorned necklaces are becoming increasingly popular and Kitty Joyas has crafted the most darling organic-style pendant on a dainty paperchain necklace.

Autumn/Winter: Cardigan With White Voluminous Skirt

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.

I've had a cardigan like this for over five years and I still reach for it on a weekly basis.

The shape of this skirt along with the soft ivory adds an expensive feel that's well beyond the price tag. 

The oversized woven bag has become a highly sought-after accessory this year and this one by Milaner is my favourite. It's even more special in real life.

I'm not a trainer girl but Veja trainers will forever have my heart! I'm particularly fond of the velcro fastening for days when I'm rushing to-and-fro.

6. The Black Midi Dress

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

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.

I'm an avid fan of Baserange. They master basic dresses with added flair. Take the 'Ligo' dress - it's subtle in design and the open back is all the detail you need. The tie straps have been implemented for a customisable element, so you can style it as you please.

This style of slip-on sandal is popular every summer without fail.

Autumn/Winter: Black Midi Dress With Chunky Loafers

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.

This dress is truly one of a kind. I can't stop thinking about it. I'd wear it with bold earrings and slingback heels.

Miuccia crafted the shoe of dreams in Prada's platform leather loafer and it's still popular years after its revival. This androgynous style shoe juxtaposes flirty dresses beautifully.

Cushioned bags were made popular by Coach and this plush bag is every bit as considered as its designer counterpart. It fits the 'big bag' brief whilst still offering a sleek appeal due to the pleating and buttery colourway.

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.