Helping Dad Dress Better

Helping Dad Dress Better


With increasing frequency I receive questions from friends, family and readers on various matters of men’s dress.  Recently, I received a rather interesting one from a reader who is trying to help his father revamp his wardrobe after a serious weight loss.  I think this is the first question along these lines so I think it could be nice to share the exchange.  Although, to be honest, whether is be dad or son revamping his wardrobe I think the process is about the same.  Figure out what your inspiration is, what works for you and where you can get it from.


My question concerns my dad. He is 59, recovering from surgery and has lost 40 pounds. He looks fantastic and is replacing his whole wardrobe. He is trying to be fashionable but he is not sure what to buy. He lives in a smaller town in the mid-west, rarely wears a suit and his business attire is everyday casual. He is really enjoying having a 31 waist and having people come up and tell him how good he looks. He tells me very few of his friends look as good as he does. What advice would you give my dad, who is a not so young gentlemen, but would like to upgrade his look?

Thank you for the kind words.  Good for your dad for losing the weight, that’s awesome!  More men and women in our country need to do so.  Anyway, glad to provide some insight, hopefully it’ll be of use.

Regardless of what age a man is there are a few things that will serve him well when trying to better his style.  Perhaps the most important of them is dressing in clothing that fits well.  For your dad, this will likely mean altering things that can be altered, but it mat not be worth it or possible on some items because he lost that much weight and/or the cost of tailoring is greater than the value of the clothing.  What will likely be a wiser course of action will be to rebuild his wardrobe.  Since you note he dresses pretty casually I’d recommend starting with some basics – chinos, button ups, polos, belts etc.  Don’t forget shoes, any man will ruin a good outfit with bad shoes.  I’d also advise him to be willing to try new brands and new styles.  I have no idea where he normally shops but when someone loses a lot of weight they would be wise to check out new brands and stores – some of their items may be a better fit and better value at these new stores.  Obviously, whatever he buys, he should feel comfortable in.

Along those lines and of crucial importance is for him to choose items and dress in a way that allows him to feel comfortable for his age.  Some people are big on ‘dressing for their age,’ which is really a relative thing, I know – it’s really up to him to figure out what he deems appropriate for his age and what he feels comfortable in.  I would recommend he browse some blogs and online media and look for some styles and looks that he likes, find out the brands the people are wearing and/or stores they shop at.  There are actually a few blogs run by older guys – I don’t read them but Ive browsed a few in the past – names like Gray Fox and Well Dressed Dad ring bells.  Perhaps those would be good for him to read.  Or he could just check out any Paul Stuart catalog, they always feature well dress middle aged men.  I realize he may not be into this type of thing or that it may be out of his comfort zone, if that’s the case then you may have to be the one to propose brands, ideas and styles to him.  My dad doesn’t really listen to mom on these matters and would never search out other blogs, but he will sometimes heed my advice.  Hope this is able to provide some ideas or starting points.




Image from Business Insider, Paul Stuart



  1. Afraid it is too late for mine. He has sworn off dressing in anything more than a t-shirt and jeans unless circumstances require it, such as a wedding or funeral.

    Curious, why did you use the image of George W. Bush?

    • Jovan,
      I’ve put a few jabs at Obama on the blog in the past and figured I should have one or two at Bush as well. I thought him looking confused was an entertaining addition to the post.

      • Well, both have seemed equally confused about how to dress at times, especially judging by their ventures into white tie! Obama did up his black tie game recently, which is nice.

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