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Any advice on where to shop online for this or do we prefer brick and mortar chains, maybe local suit shops are better? Either way I will have them tailored to fit better if off the rack. Just help me update my look to not look like a child perpetually in jeans and street clothes.
You're right to emphasize fit, but there are many other factors, not least of which is your budget. If you can only spend $200-300 per suit you simply won't get the quality that you can obtain at higher price points.
If you're really interested in getting good guidance on clothing I suggest that you start frequenting Ask Andy About Clothes.
Brooks Brothers has a good selection of everyday suits, and the company runs its own outlets which have better deals on suits and shirts, though you can do well if you time the sales. Many department stores have ranges of suits to fit most anyone, and at different price points, so Macy's, Bloomingdale's, Nordstrom, Lord & Taylor, etc. are generally good places to look.
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All the world's a stage, and all the men and women merely players: they have their exits and their entrances; and one man in his time plays many parts, his acts being seven ages.
~William Shakespeare (As You Like It Act II, Scene VII)
if you live in certain big metros, Bonobos--the online menswear/prep shop-- has try-on boutiques where you can actually get sized & see the garments. You don't get to take it home with you though since the actual item is shipped to your door from their warehouse.
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