Originally Posted by ShoeFinance77
What are some things I can do to update the look or at least pull it off and not look as if I'm nostalgic for the 90's?
Simply wear it unself-consciously. No man looks his best when he's constantly second guessing his choices and worrying over whether what he's wearing looks okay. If you put on that suit, and are convinced that it's a good choice and that you look fine in it, few people will think there's anything wrong with it. ("Few" people. That doesn't mean some people who care about fashion trends might not have a negative opinion of it. But in the real world, such people are a small minority.)
Does it represent current men's fashion? No, not really. But so what? None of my dress shoes are "sleek." I don't care for sleek dress shoes, at least not on my size 13EE feet. I like 1960's vintage Florsheim Royal Imperial gunboats. More casually, I wear penny loafers. Do my preferences reflect what's currently in fashion in terms of men's footwear? No, not really. But I couldn't care less. I also prefer traditional-fitting (not slim) dress shirts. I prefer neckties at least an inch wider than the 2.25" neckwear beloved by fashion magazines and pop culture celebrities at pseudo-events.
Heck, I even keep my face clean shaven, when everyone knows that the "I shave every 3rd or 4th day" look is what's currently fashionable.
I know that I look good. I like my appearance. I'm quite comfortable with my sartorial choices. And at the risk of sounding immodest, I don't believe these choices are in any way holding me back in life. Not professionally/financially, nor socially.
Point being, the suit in question is not so old fashioned as to be archaic or costume-like. It's not like you're going to look like a character from Downton Abbey, brought forward by an evil wizard to the 21st century. People aren't going to stare at you as you walk down the street. So if you like the way the suit looks on you, wear it. To the office, to social events, wherever.
So long as you believe you look okay, and you're not fretting over whether you should have had the lapels restyled (yeah, right), there's no problem. None.
If you can't work up this level of comfort with your suit, don't bother trying to have a tailor make it look more modern. Just sell it, and use the proceeds to buy a new suit.
PS - When I go out to dinner this evening, I'll likely be wearing a navy Brooks blazer, older than your Oxxford suit. And maybe - just maybe - a bow tie. And I will like the way I'll look. And I'm pretty sure my date won't be so embarrassed by my appearance as to fake a headache and end the date early. I'm reasonably confident we won't be given the table by the kitchen door, due to my looking like a refugee from season 3 of "Frasier." And it's pretty unlikely anyone in the restaurant will think to themselves, "Gee, he's not really ugly, I suppose, for a middle aged guy, but he'd look so much better if his lapels were narrower and his blazer tighter."