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What to wear with black silk shirt?

Mr Tickle

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So I've got to the point where I'm reasonably happy with my daytime business and casual wardrobes. What I am lacking is though is things to wear for the more dressy side of casual evening wear - i.e something a bit more than a pub crawl around town with the boys, and a bit less than a formal black tie event.

Something like drinks in a nice city cocktail bar or dinner at a nice restaurant. This is a bit of a blind spot, I've found, for the standard business casual/workwear/streetwear categories of men's casual wardrobe building.

So as a starting point I've invested in a handmade black silk shirt - it's matte rather than shiny as you might think when you picture a silk shirt. I've tried it here with white trousers for contrast, and a pair of dark brown flannels for a more monochrome look. They both look ok to me.
What about jackets? I don't think I'd want to go as formal as a tailored jacket for the type of look I'm aiming for. Maybe a nice bomber jacket or leather jacket? (Or would that be too casual)?

Any suggestions for other ways to put an outfit together around a shirt like this?

PXL_20220919_095326307.jpg PXL_20220919_095341784.jpg PXL_20220919_094808327.jpg PXL_20220919_094734543.jpg
 

mensimageconsultant

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You aren't new here. You probably have heard of Yoox. Some high-fashion casual jackets (or cheap knockoffs), lighter than a bomber jacket, probably would work with that, but it sounds wasteful just to buy a jacket for a shirt and dressier jackets are much likely to pair well with it. Ideally you'd show what jackets you already have. A rustic-leaning jacket isn't worth trying with that shirt.
 

Mr Tickle

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Ok, thanks - I'll take some pics with some of my jackets!

I am not against the idea of buying a new jacket to go with it, but it's more that I am buying the jacket to build a look, rather than just to go with the shirt. Casual but dressy is a bit of a blind spot in my wardrobe at the moment. I've noticed that when I have the opportunity to go to a nice restaurant in the evening, or to a bar for cocktails, is the time I am most likely to be at a loss for something to wear.
 

Mr Tickle

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You aren't new here. You probably have heard of Yoox. Some high-fashion casual jackets (or cheap knockoffs), lighter than a bomber jacket, probably would work with that, but it sounds wasteful just to buy a jacket for a shirt and dressier jackets are much likely to pair well with it. Ideally you'd show what jackets you already have. A rustic-leaning jacket isn't worth trying with that shirt.
Ok so I took some pics with some of my smarter casual jackets:

Light suede:
PXL_20220922_154025888.jpg PXL_20220922_154759811.jpg
Moleskin bomber:
PXL_20220922_154144259.jpg
Dark brown corduroy:

PXL_20220922_154234711.jpg

Olive suede:

PXL_20220922_154355794.jpg

Am I heading along the right lines with any of these? Would a different pair of trousers work better with any of the shirt/jacket combos?
 

mensimageconsultant

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Thanks for the new batch of pictures. From a color-coordination standpoint, all that works, but the jackets are slightly too casual for evening. Medium- or dark-gray suede (designed with the pockets toward the waist) is the recommendation if you want a jacket in the sweet spot of dressed up but not work-like.

Also, the pants are too light-colored for evening wear.
 

Mr Tickle

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Thanks for the new batch of pictures. From a color-coordination standpoint, all that works, but the jackets are slightly too casual for evening. Medium- or dark-gray suede (designed with the pockets toward the waist) is the recommendation if you want a jacket in the sweet spot of dressed up but not work-like.

Also, the pants are too light-colored for evening wear.
Thanks for the reply, I agree with the points you make, particularly with the pants being too light.

I think it's likely that this is an issue for a lot of people interested in menswear at the moment. We feel we've got daytime smart/business casual pinned down to some degree. Particularly in the context of the ongoing casualization of society and the reduced need for everyday suiting/ tailoring etc, which simplifies things somewhat.

This means that the occasions that we are most likely to want to dress up are likely to be evenings. And in the evening, the rules are completely different. The dark top/light bottom dichotomy goes out of the window, for example. And white and pale blue are no longer the go-to colours for shirts. Tweed, flannel and other textured materials which are staples of daytime smart casual or classic looks are not appropriate. But we certainly don't want black tie. All of this is rarely addressed in online menswear/style advice and discussion.
 

breakaway01

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What I am lacking is though is things to wear for the more dressy side of casual evening wear - i.e something a bit more than a pub crawl around town with the boys, and a bit less than a formal black tie event.

Something like drinks in a nice city cocktail bar or dinner at a nice restaurant. This is a bit of a blind spot, I've found, for the standard business casual/workwear/streetwear categories of men's casual wardrobe building.
There is a very large gap between "a pub crawl around town" and "a formal black tie event".

For a nice city cocktail bar or dinner at a nice restaurant, I do think that one could still very reasonably wear a sport coat (with or without tie) and dress trousers -- in fact that would probably be my preference. I disagree that tweed or flannel is inappropriate in this setting.

If you want to go a level less formal, I agree that the lack of a single convention makes it more difficult to apply a simple set of principles or rules. It's more than just "do I wear this with darker or lighter trousers" -- it's the whole look. You have to look at different outfits/looks and determine for yourself what you feel more comfortable with. For example, do you want a more Western wear or workwear look, a 1970s-derived look, a modern Italian casual look, etc. Many possibilities, but I would try to be coherent to one of these rather than trying to mix and match pieces from different looks.

In your case, I wouldn't have purchased that black silk shirt without having had some idea of what look you're going after. It's a common problem here on SF -- people posting "I bought this pair of shoes, what do I wear with them?" To me that shirt reads as possibly something you could wear with jeans (Wranger Wranchers come to mind), roper boots, and a trucker jacket (Western wear) or possibly in an outfit with straight or slightly flared 5-pocket trousers and Chelsea boots. In either case with another button undone. Just two possibilities.
 

mak1277

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I think you’re overthinking it. You can definitely wear light pants at night. I wouldn’t wear those specifically though…if I was to wear cream trousers I’d want to make sure they were well tailored with a crease. The rumpled chinos don’t match the chic-ness of the shirt.

I’d personally chose light grey over cream, and wear it with black loafers.

here’s a good article

 

mak1277

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I also wholly disagree with the idea that you can’t wear white/blue shirts, tweed or flannel at night. Wherever did you read that?
 

Mr Tickle

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I also wholly disagree with the idea that you can’t wear white/blue shirts, tweed or flannel at night. Wherever did you read that?
Not so much something I have read, more an observation from my own experience - it isn't something that tends to be done, here in the London at least.
Not saying it never happens of course. Just that you don't tend to see well-dressed people doing. It.
 

Mr Tickle

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I disagree that tweed or flannel is inappropriate in this setting ...

For example, do you want a more Western wear or workwear look, a 1970s-derived look, a modern Italian casual look, etc. Many possibilities, but I would try to be coherent to one of these rather than trying to mix and match pieces from different looks.

In your case, I wouldn't have purchased that black silk shirt without having had some idea of what look you're going after. It's a common problem here on SF ....

possibly you could wear with jeans (Wranger Wranchers come to mind), roper boots, and a trucker jacket (Western wear) or possibly in an outfit with straight or slightly flared 5-pocket trousers and Chelsea boots. In either case with another button undone.
Just quoting the specific parts of your post I wanted to respond to - taking them in order:

It's just not something I'm used to seeing here in London. Tweed/corduroy/flannel etc - countrywear basically - on well-dressed people out for the evening in the city. I know most people using this forum are American and as I travel to the states frequently, I also know conventions are different there!

I'm not after a western wear look (it's very outside of my frame of context)...I guess modern Italian casual would be closest to what I had in mind when I bought the shirt.

And I wouldn't say I bought the shirt without having some idea of what to wear with it - it's more like I bought it with the intention that it would form a starting point for exploring a new menswear paradigm I I haven't really explored before. Smart casual eveningwear is the term for it I guess. Unlike say business casual or smart casual it's not something I need a "rotation" for, as it's not by any means everyday wear. So just two or three outfit combinations should be fine (thinking of a purple silk shirt as the foundation of the next one).
 

breakaway01

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OK fair. I think a black silk shirt is definitely on the more challenging end of smart casual. And purple silk even more challenging.

If you are going for Italian then those trousers definitely won't do it. Better drape, not wrinkly, sharp crease. Thinner dress belt.
 

Mr Tickle

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OK fair. I think a black silk shirt is definitely on the more challenging end of smart casual. And purple silk even more challenging.

If you are going for Italian then those trousers definitely won't do it. Better drape, not wrinkly, sharp crease. Thinner dress belt.
Are the brown trousers shown in a couple of the pics closer? I also have a pair of gray wool trousers on order, which might be along the right lines?

Not so worried about the getting the jacket right, at the moment. As I'll be wearing it inside, in an environment where a jacket won't be necessary, so I can wear it with an overcoat which will be removed.
 

Mr Tickle

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Ok so - got a new pair of tailored grey trousers - still a bit too casual? (Ignore the length for now).
One outfit idea here, very monochrome looking but I think it works. Obviously the idea is the coat would come off. Any good? PXL_20220926_110813443.jpg PXL_20220926_110944312.jpg
 

breakaway01

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That works for me. I think a monochromatic look works well for a black shirt.
 

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