What should I be wearing?

Hey Lefty,

Yeah, I went from 230 down to 180. So I'm looking for a whole new way of dressing.

Originally Posted by charfan9

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Hey Lefty,

Yeah, I went from 230 down to 180. So I'm looking for a whole new way of dressing.

How do you want to dress? I mean, you're retired, you can and should do whatever the hell you want.

Originally Posted by WhateverYouLike

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Alternatively, you can ask a female friend to help you shop at a mall. Women always have a highly developed sense of fashion.

Fashion yes. Men's style... I disagree. I don't think women in general are any better than men in general about picking men's clothing.

Just as I would completely suck at picking out which individual piece of clothing a woman should wear, I don't think they would know what individual piece of clothing I should wear. However, they are pretty good at "rating" the ensemble. Ie, they know when a man looks good.

I think we're making this too hard. My read is the OP wants to dress well for his age, newly fit body and environment. He lives in Mississippi, so let's not try to get too carried away. I'm assuming he's not interested in becoming a SF maven. This is for every day retired casual.


Get some khakis. Try J Crew. You should be able to find a good cut there, not pay too much money and not have to worry about babying them.

Get some jeans. Try Levis 501s as dark as you can find them. Were I you I wouldn't fool around with shrink to fits. Try them on and get some that fit well.

Get some button up shirts. Spring is coming, Mississippi gets hot. Look for something light weight. Again, J Crew might be a good place to look. Consider linen. Pick up some Brooks Brothers slim fit OCBDs.

Get some polo shirts. Some will disagree with this, but they're great for everyday casual, particularly with the warm weather you face most of the time. Try J Crew again, or Target for that matter. Be aware of fit.

Shoes. Now this is where you'll suffer severe sticker shock, but good shoes will set you apart from the herd more than pretty much anything else.

To start things off, consider a couple of inexpensive knockaround shoes.

Taupe suede bucks:




And boat shoes:



Another possibility could be some Clark's desert boots:



Beyond that, you need to consider something better like Aldens or Allen Edmonds. These will be expensive, but if taken care of can last you for the rest of your life. I would suggest some plain toe bluchers:




Norwegian split toes:




And Indy boots:




Now, beyond that add a pair of gray and a pair of tan wool trousers, plus a navy blazer, throw in a couple of repp ties and you'll be set for most situations you'll face. You can get a lot more complicated than this (and look even better), but this is simple and basic. It will make you look good, and much better than 90% of the people around you.

Originally Posted by phxlawstudent

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Fashion yes. Men's style... I disagree. I don't think women in general are any better than men in general about picking men's clothing.

Just as I would completely suck at picking out which individual piece of clothing a woman should wear, I don't think they would know what individual piece of clothing I should wear. However, they are pretty good at "rating" the ensemble. Ie, they know when a man looks good.

It was a joke. Women and gay guys dont know much more than anyone else.

Thanks AlanC,

You got it right. I do well in 501's and Wranglers. I picked up a few polos by "Nautica" and they seem to look pretty good. I try to stay away from stripes, and stay with solids. Any suggestions on colors? Thanks again. I DONT need to be a "Fashion Plate", I just want to look good.

Light blue, green? Without your eye color and skin color, it is mostly a guessing game.

Button-down shirts, polos, and jeans are fine, but you really should include some patterns (like a subtle seersucker), some lightweight pants (tissue chinos from Ralph Lauren, for instance), and (for the hot weather) some linen.