A week in work outfits with Project Hutton Account Manager, Ailish Dempsey

All about blending comfort and style.

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 Project Hutton’s Account Manager Ailish Dempsey, “baggy pants, an oversized blazer and a staple tee” is her go-to outfit for office days. Switching between shoots, meetings, work-from-home days and stints in the studio, Ailish’s work wardrobe is all about blending comfort and style. Adidas Sambas, wide-leg denim and an oversized black coat are all mainstays in her Monday-to-Friday looks. Below, she shares a week of work outfits.

Monday

Can’t look further than my favourite Cos pants and a thrifted blazer for a sunny Monday afternoon of meetings. My pants need a better steam, but letting it slide for a Monday.

I find baggy pants, an oversized blazer and a staple tee (Uniqlo) my go-to when we are in the office. A pop of colour below and a light shade above [usually] does the trick. [It’s] always handy when you have an office and studio space that provides west-facing afternoon sunlight… [to help] bring this outfit to life.

Tuesday

I’ll go for a bit more of a casual look for a Tuesday without meetings. Girls in the office are probably sick of seeing me in my baggy jeans… but they’re too comfy to ignore!

The jeans are Source Unknown that I found on Depop for $60! Absolute steal. The pointed boots are vintage [I] found on eBay years ago for $35 and the shirt is an old thrifted Nautica number. The sunnies are Halycon and the scarf is also Depop.

Wednesday

[On] Wednesdays we work from home, but on this occasion I went in for the afternoon to close up for a shoot at the studio. I’d call this outfit my ‘work from home and late call up to the office’ kit.

My Mango gumboots are probably my greatest purchase from 2020… [they’ve had] upwards of 300-plus wears and are about to fall apart. How each item in our wardrobes should be! This chunky green knit is an old thrifted number from NYC a few years ago, and the shorts and bag are Depop purchases.

Thursday

I did something no other girl has done and bought Adidas Sambas! This is another pair of shoes with close to 300 wears. They truly do go with anything. I get the hype.

This is a skirt but I’m a firm believer in wearing clothes in different ways, so thought I’d make it a dress for a sunny Thursday. I bought it from Incu a few years ago.

Friday

Pictured: massive dag getting their photo taken. I would like to see the statistics on people who work in PR who own oversized black coats. Can someone run a survey on this?! The black coat is thrifted and the belt is Zara. Baggy pants again (no surprises) and the shoes are thrifted (sorry).