A week in work outfits with The Upside’s Head Designer, Ashlea Holdsworth

“My shoes are Isabel Marant but I think my best accessory is a giant coffee in my Keepcup.”

Working in a creative role, it can be difficult to know how to dress for the day. Instead of having a set uniform of crisp white shirts and tailored black pants (as much as I love both), an ever-changing schedule means every morning requires a set of questions. Am I running around, or just sitting at my desk? Do I need to dress specifically for a project? And most importantly, will I be in the background of someone’s TikTok?

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For The Upside’s Head Designer Ashlea Holdsworth, getting to wear items she designs herself is one of the most rewarding parts of the job. Her work wardrobe consists of comfort-focused pieces from The Upside (of course), like flared leggings, body suits and tennis dresses, paired with designer shoes (she favours Gucci and Isabel Marant) and dreamy vintage pieces sourced on her travels. Below, she shares a week of work outfits.

Monday

Mondays are a little bit of a rush in the morning. I have two young children so I’ve often already juggled a day before the day begins. I opt for something effortless so I grab one of our latest releases, the Plie Pointe Bodysuit from our dance capsule. I love playing with proportions so I pare this back with a loose silhouette on the bottom. In our campaign, we styled this bodysuit with a red Celeste Pant but I also love the navy with a natural colour so today I’ve teamed it with a pair of wheat-coloured vintage men’s workwear pants from the ’40s I thrifted from Ghostwood Vintage in Byron. I’ve styled these with my Gucci slides. I wear vintage most days and love pairing it with my pieces from The Upside.

Tuesday

Can you tell I’m willing to put in the hard yakka this week? I love vintage so today I’ve opted for some King Gee men’s workwear shorts I bought online. I love the way these shorts fit, low on the hip and relaxed. I’ve styled them back with our upcoming Hayley Tank and Piper Knit Cardigan (coming out in April). My shoes are Isabel Marant. I love mixing tough masculine and soft feminine pieces, the cardigan here really balances out the look.

Wednesday

On Wednesday I work from home – please note my side-kick/shadow, Magic. Magic follows me all around the home office and for our lunch break we love to go for a walk around the block. So that I can transition easily into work I’ve popped on one of my new favourite leggings, our Florence Flare in the Pure Peached fabric. I’m not just saying this because I designed them but they are truly the most buttery-soft fabric and they just wear so well, I feel so confident that they are going to stand up in my Pilates and yoga workouts plus work as a transition piece you can wear beyond the studio.

I also love that they are made from 75 per cent recycled fibres. Today I’ve popped them on with our Laura Tee which is a great oversized tee, this colour is coming out in September. As my whole look is pretty relaxed, I’ve added a crochet shirt in case I get a little chilly and my Arizona Love Sandals.

Thursday

We’re meeting with our Creative Director Jodhi Meares today to go through our next range review, this is where we go through the collection piece by piece and decide which pieces are going ahead. It was lovely and sunny when I woke up so I opted for pieces that felt light and bright, like my white vintage upcycled linen shirt from HerCloLab. This shirt is made from a recycled tablecloth. The embroidery is exquisite and I wear this piece constantly as it goes so well back with pieces in my wardrobe like the Celeste Pant. My shoes are Isabel Marant but I think my best accessory is a giant coffee in my Keepcup.

Friday

Fridays in the office are fun, we like to get together for a few team drinks in the afternoon to celebrate the week. I decided to wear the most popular piece from our tennis collection, especially while I can make the most of it with the warmer weather. I love tennis-core styling, I think it’s a trend you can have a lot of fun with. I’ve teamed it with a pink Reworked Vintage Jacket I picked up in Paris to shield me from the office aircon! We do a yearly design trip to Paris; this is a place I love to hunt for one-of-a-kind pieces, I also just also love spending time there observing people, how they move and dress. My sandals are Arizona Love.

You can explore The Upside’s range here.