Oversized Shirts Will Always Have a Place in My Wardrobe
They hit that sweet spot between smart and comfortable.
As we (very gradually) welcome the arrival of spring in the UK, I’ve been packing away my heavy wool jumpers and reacquainting myself with the items in my wardrobe that haven’t had a good airing in a while - and that includes getting a few very seasonal pieces out of suitcases too. When sorting it all out, I realised just how many oversized shirts I own that make up a bulk of my spring/summer/early autumn wardrobe.
It made me excited to wear them again - like going shopping but in your own wardrobe - and had me thinking about all the ways I’ll style them this year. Then I stopped to ask myself what it is I like so much about an oversized shirt, and why this, over other pieces I unearthed for the upcoming seasons, got me as energised as it did. After all, it’s just a shirt.
I’m a big fan of relaxed tailoring (as you’ll see in this post, where I recreated five tailored looks from Jil Sander, The Row and more), and the oversized shirt is perhaps the epitome of that. I love the smartness of it and the nod to classic styles that have lasted decades, while the relaxed, loose fits make this kind of clothing easy and comfortable to wear.
I love the sharp look of a button-up shirt but I don’t love the feel of a tight collar buttoned around the neck (too many bad memories of crappy school shirts and top button enforcement by teachers). Being a larger fit than your ‘regular’ size, an oversized shirt bypasses any discomfort entirely. There’s no pulling at the collar trying to loosen it and create space between fabric and skin, there’s no straining at the buttons because it doesn’t quite fit right in certain areas of your chest, and there’s no scratching at the wrists because the cuffs are a little too close.
Comfort aside, I love the look of an oversized shirt. They always add shape to an outfit and you can tuck them in and out of trousers/shorts/skirts to create a different silhouette each time. Here are five of my favourite oversized shirts, and how I’ll be wearing them this spring.
Look 1
This shirt is a long-sleeved, light grey flannel style with a grandad collar. I bought it five (ish? I think?) years ago from Muji and thanks to its slightly thick fabric, it’s perfect for early spring when a linen or cotton shirt is too light. It has a long length so I love wearing it tucked out over trousers like here, to show off its proportions, as well as underneath a hip-length vest so you get that contrast of short and long. There’s a similar seersucker shirt in the latest Ines de La Fressange x Uniqlo collection, in white and navy. I’d size up if you like a looser fit.
Look 2
I’ve worn this shirt a lot since I got it late last year. It’s made from 100% linen and despite its colour, has no sheerness at all. When I button it all the way up, it looks smart and sharp but doesn’t feel restrictive around the neck and it looks equally as good with the collar open. The sleeves are also pretty long (at least on me) so I can scrunch them up slightly to create more shape in the arms. I’ve loved wearing it with tailored trousers and flats, like this look, for dinner or drinks when a little more effort with your outfit is required.
Look 3
This is another shirt I’ve had in my wardrobe for years, and have worn so much, that it’s starting to get a bit faded around the edges. It’s a long, very oversized shirt made from light cotton that’s perfect for warmer days and has wide, shortish sleeves that land on my forearm. It looks great tucked out and over the top of trousers as it is so long and loose-fitting but I love to loosely tuck it into waistbands too, like here, when I want to feel more streamlined and pulled together.
Look 4
Last summer, I got this shirt from New York-based brand DL1961 (it’s no longer available but there’s a similar version at Arket). It’s a white, lightweight 100% linen shirt with a longer rounded hem at the back and a relaxed fit, and I practically lived in it during those summer months. It’s loose and cool enough for those hot days when you want to protect your skin from the sun, easy to wear with trousers, and perfectly layer-able when you need to pair it with some warmer pieces. I’m not a big believer in telling people you have to have certain pieces in their wardrobes… but I may just make an exception for a loose white linen shirt. You won’t regret it.
Look 5
This was another Uniqlo U buy last year (those collections are always good to look at for oversized shirts, jackets and T-shirts). It’s a sage green shade with slightly lighter stripes so it ticks the box of a little colour when I want to wear something other than white, grey or navy. I always button this one up when I wear it as I like the pointy collar to be in focus, plus I like the overall look it creates. The sleeves are wonderfully big too, so I keep the cuffs buttoned and push them up slightly to puff those sleeves out even more. It’s great for wearing with tailored trousers, and can be smartened up or given a casual spin with trainers, like here.
Any items marked with * have been kindly gifted by brands. All thoughts, picks and reviews are my own.
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I love an oversized shirt…. On everyone else but myself! At 5’1” and a small build, I often struggle to wear them without feeling like they’re wearing me. It feels like there isn’t enough décolleté or wrist I can show to make up for it.
My wardrobe wish list/Notes even says “Button downs never make me feel like they look in a product listing photo. Find out why before you buy any others!”
Any ideas? Is it a matter of tailoring? I’m willing to invest in the garment if it means enjoying it
Great outfits! Love your signature silhouette x