The tailoring with a tee look has been around for a while.
It sounds like a perfect marriage of casual and formal; something sharp like a suit matched with the casual nature of the t shirt. However, it isn’t as easy as it sounds to put together one of these looks and have it coherent.
I’ve already talked about tailored pants and tees before, but this time I want to talk about it in a whole outfit context. And, while I’m at it, share a bunch of inspiration images.
From Super Casual to Suiting
There’s no hard and fast rule as to whether a t shirt is going to work in your tailored outfit, other than maybe not mixing a crappy looking tee with a super sharp suit.
The reality is that sometimes all it takes is throwing a sport jacket over a tee and jeans look, and other men will look great with a tee underneath a double breasted suit (albeit in a casual fabric).
I’ve never personally worn a tee with a suit, but I’ve seen some crackers like this image of Luca Rubinacci wearing a linen DB over a mariniere.
Under A Sport Jacket
This is the realm where I think tees can work the best.
Most men will opt for a single breasted sport jacket to do this, because SB usually infers a slightly lower level of formality than DB (depending on your personal viewpoint). The only real no-no when picking a sport jacket to throw over a tee is using worsted wool.
But you shouldn’t really be wearing worsted wool for a sport jacket anyway. It’s a fabric for suiting, and any tailored jacket in worsted wool that’s being sold as a sport jacket is realistically more likely to be an orphaned suit jacket.
I’ve used fabrics for every season in sport jackets that I’ve worn over tees, such as wool, cashmere, linen and flannel. Sometimes the tee is the only layer under the jacket, other times it’s the base layer.
Linen jacket with seersucker trousers – perfect summer casual look.
An in-between seasons look this time – with linen, denim and wool scarf.
Using the tee as a base layer while wearing a middle layer over it and class it up a bit, or just provide more visual interest.
Even graphic tees are within the boundaries!
This tee and the rugby top were made for each other.
I matched the tee to the orange stripe running down this tweed jacket.
What kind of tees are best?
This right here, is the area where many men trip up. I’ve tripped up here too when I first started experimenting.
It’s all in the fabric and construction.
Vintage – or vintage inspired – tees are usually made from a thicker, more rugged fabric while many cheaper or modern tees are made from a softer, stretchier jersey weave cotton (the kind your pyjama shirts are made from). The former looks great, while the latter will just look out of place. Jersey cotton tees usually have a poor construction around the ring of the neck too, which further damages the overall look.
Wearing a graphic tee can also be a hot ticket to an unfavourably clashing look but this isn’t necessarily so. It’s just important to make sure the overall outfit is still pretty casual.
Oh, and of course, the fit needs to be spot on. If it’s baggy, it’s going to instantly look bad.
So far, I’ve personally found two brands with tees that are perfect for combining with tailoring because of their vintage inspired ruggedness and sturdy construction. The first is Bronson Mfg. Co, from whom I have two great tees that I wear regularly:
The second is Uniqlo. Particularly, the Uniqlo U tees. The great thing about these is that they’re rugged, with great construction, and they only cost $19.90AUD at full price. I’ve found the fits to be pretty good too. These only come in a handful of plain colours, but that’s good enough to cover your basics if the tee and tailoring look is something that you want to do regularly.
This Velvet Underground one was a limited run in 2018. 
The Uniqlo ones are really hard to pass up for the value.
I’m sure there are quite a few other options out there for good quality tees that would look the part with tailoring, but these are the only two I have personal experience with.
Conclusion
Wearing a tee with your tailoring is a great way to give a casual edge to an otherwise classical outfit. It’s worth giving it a try.
Do you combine tees with your tailored clothes?
See you next time,
Sam
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