WAYWRN: Classic Menswear, Casual Style - Page 968
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Leaving aside the untucked shirt, and perhaps its colour, I see no problem with this combo. Loafers are sporty/casual and so fit the ensemble in the casual style sense. The sleek black jacket with ribbed cuffs and the smooth black leather of the loafer work well together. The only possible complaint is that loafers are a "summer" shoe and don't fit an autumn (fall) ensemble. But that "rule" is quite flexible, and loafers with a jacket - particularly a stylish and relatively lightweight leather jacket - seem quite acceptable. I might have bridled at no socks in autumn, but that is a personal choice. The watch creams the lot. Chocsosa looks good here.
^This. I live in California. As I speak right now, the weather outside in late October is 82 degrees where it will dip to 68 in the evening. So this is summer time weather for most places in the world. The leather jacket is very lightweight and was intended that way when purchased due to the fact that I live in Cali. I have other winter appropriate leather jackets but for a cool night time out in the bars I think it does suffice. Now if it were 50 degrees and less than it would make sense in terms of not wearing loafers but that is not the case. The untucked shirt is a shorter shirt that is not meant to be tucked. its a very casual shirt and when I got too the bar, I did take off my jacket and was left with a chambray shirt, denim jeans and loafers. Not trying to overthink it but was more looking for utility and being casually peacock dressed. Thanks Stiva!
Woolrich Travel Jacket, Johnstons cashmere scarf, M. Cilento unlined deerskin gloves, Scaglione merino Air Jumper, unfused Vincenzo Di Ruggiero cotton shirt, Canali flannel pants, Edward Green Dark Oak calf belt, Cheaney country grain boots, Mk XV on buffalo strap
Without jacket (Click to show)
If that means what I think it means (the Cheaney FS029 from their factory shop), then yes :-)
A better pic:
the infamous shots that made me get 'em (Click to show)