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Repurposing dress shirts for casual wear

oilgeo

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Hi guys, I've been lurking on these forums for a long time now and have learned how my suits should fit and that M2M and tailored shirts can eliminate my previously insurmountable battle with billowy dress shirts. If you don't want to help me out please move along because I am about to ask for an internet style lesson here.

Since leaving university almost 6 years ago I've been working in the oil and gas industry non-stop trying to further my career. This has left me with a boatload of well fitted dress shirts ranging from light blue OCBDs to gingham patterns, stripes and plaids. I've got a few bespoke suits and a couple of blazers that I typically wear with chinos or unmatched trousers to the golf club for after-hours meetings with clients.

Only recently have I managed to get myself into a healthier work/life balance state of mind and I am pretty much lost on casual style. When I go out to the pub with my buddies I don't want to just dress in my old ratty graphic tee's anymore and have replaced all of my old jeans with nicer dark blue denim. My wife and I are starting to spend more time relaxing on the town during the week and on weekends when previously we would take off to the mountains at every opportunity. We have also started to take monthly trips to Europe and I don't want to look too touristy (but I don't necessarily want to look European, I am a redneck at heart after all), nor do I want to look business casual all the time. Is it acceptable to pair my dress shirts with jeans for a casual look? I don't really want to go buy all new shirts to start updating my style and I'm not a huge fan of polos.

Also, nearly all of my shirts need to be tucked, so I'm not sure if this is a good casual look or if it would be better suited to an older man. I'm only 28 after all and don't want to end up looking like I'm 40.
 

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