There are some workdays when you know you’re not going home at five-thirty. You’ve got drinks planned, dinner booked, or somebody has uttered the dangerous words “shall we just go for one?”, and suddenly your outfit needs to last from your morning coffee right through to whatever happens after work. This is exactly the sort of look I want on those days: comfortable enough to wear for hours, but smart enough that I don’t feel like I need to change before heading out.
The rugby-style dress is doing most of the work here. Rugby shirts and rugby-inspired tops are having a real moment this autumn, and this striped midi dress gives you that same trend without feeling like you’ve dressed specifically to chase one.
The shape keeps it easy and wearable, while the collar gives it enough structure to work for the office. More importantly, it looks comfortable. This isn’t an outfit you’re going to regret choosing by lunchtime because something is digging in, riding up or requiring constant adjustment.
I’ve kept the rest of the look mostly black, which makes the dress feel a little smarter without overcomplicating things.
The sheer black tights are an easy autumn addition and, together with the ankle boots, make the whole outfit feel more polished. I particularly like a block-heeled boot for this kind of day because you get a little bit of height without committing yourself to eight hours at work followed by an evening balancing on uncomfortable heels.
Then there’s the jacket.
A black faux-leather jacket instantly gives the dress a slightly sharper edge. It’s smart enough for going out after work, but it doesn’t turn the outfit into something that feels overly dressed-up during the day. The dress, tights and jacket are all from Yours Clothing too, so there’s a decent amount of genuinely plus size fashion here rather than building the whole outfit around pieces with a very limited size range.
And finally, the bag has to be practical.
For an all-day work outfit, a tiny evening bag simply isn’t going to cut it. You need room for all the things that mysteriously accumulate during a working day, but you also don’t want to head into a bar carrying something that looks like laptop luggage. This oversized black shoulder bag sits nicely between the two: roomy and useful, but still sleek enough to stay with the outfit into the evening.
That’s really the trick with a good work-to-drinks outfit. It shouldn’t feel like two separate wardrobes fighting with each other.
You just want clothes that are comfortable enough for the day, smart enough for later, and let you shut the laptop, pick up your bag and go.
