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Help me rebuild my quinquagenarian wardrobe from scratch

Shotgunner

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Hello all. Long timer lurker, first time poster. I’ll try to give you the rundown as concisely as possible here…

Age = 50. Height = 6’0”. Weight = 210 lbs. Pant size = 36x33”. Jacket size = 44” or thereabouts.

Body shape = generic Midwestern American “I used to play football in high school”. Not obese, but no longer highly athletic. Sort of like an Ed O’Neill in his early 50s. In fact, I’ll paste a picture of an (older-age) Ed below. (Not in his 50s in this pic, but a pretty good representation of my proportions.) Not putting on any more weight at this point, and slowly taking a bit off now that the kids are off to college and there’s more time for working out.

Location = Des Moines, Iowa, but considering relocating soon.

Lifestyle = typical suburbanite stuff of medium-company exec, i.e. work, volunteerism, reading, escaping a couple times per year to larger cities with better restaurants and art galleries, etc. Also some outdoor stuff like gardening, fishing, and upland bird hunting.

Ok so, here’s the deal. I’m wanting to burn everything in my closet and start from scratch.

Pre-COVID life used to be simpler, to be honest, because I’d wear a conservative-colored business suit / shirt / tie every day. Usually something “OK” from Nordstrom, when I lived near one. Sometimes as cheap as J.A.B. crap. Occasionally I had a few made-to-measure.

Now, post-COVID, almost all the work is remote. We spend a couple days a week in the office, but it’s all casual now. Often casual in a way that looks stupid on an older person in their 50s or 60s, which is part of the problem. The old suits in my closet are gathering dust and increasingly out of style. I only wear one about four or five times per year. I’m fairly well stocked on casual or outdoorsy clothes, but have nothing in-between for going to a smart-casual event or jacket-recommended restaurant.

I’m at an age where I’m wanting to keep life simple. I feel like I could toss everything in my closet, and rebuild with less (but better selected) clothing that would give me a variety of options for all types of events, circumstances and seasons.

Help me spend my money and find a sweet spot between looking like a total dandy, and looking like an average dad-bod slob.

Thanks

1719345065637.png
 

Shotgunner

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Oh, and I mean don't hold back on anything, including all new shoes, boots, belts, etc.

Emerging from two decades of child-rearing feels like being a caveman who has been unfrozen. I've even let my wristwatch collection fade away to a few non-working and irreparable quartz and mechanicals. (I'm looking at a new Tissot PRX as a low-price way to kick-start that again.)

Offhand, the list that I've written for myself is:

  • 3 new suits, medium quality, of practical colors that could be worn year round on occasional business trips, or out to dinner, with our without tie.
  • 6-8 good quality dress shirts, plus various shoes and belts, to add some variety to the suits. In other words, when a co-worker sees me at a conference every four months, he doesn't say, "Oh, there's Bob in his usual 'Wednesday Travel' outfit."
  • Something less casual than a 2-piece suit, although "blazer" has a bad connotation in this part of the country. It's like everyone here wearing a blazer looks like a life insurance salesman stuck in the 1980s, with a blue blazer, brass buttons, and baggy tan slacks.
  • Something even less casual than bullet #3, but a step above jeans. I suppose that could mean the ubiquitous polos-and-chinos, but not sure if that works well for someone in their 50s. And I don't want to look like the typical "bro dad" who golfs, goes to sports bars, and calls his kids "sport" and "champ".
  • Hot weather smart casual = some kind of shorts when someone invites us to an event that will be outdoors in July or August.
  • Outdoor / workwear. This is about all I have that is salvageable and not going into the charity shop pile. E.g. some good quality hunting moccasins and Le Chameau wellies that will probably last until I die.
Help me fill in the gaps, please!
 
Last edited:

mensimageconsultant

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Linen pants, corduroy pants, and moleskin pants would help avoid some of the archetypes you mention.

Patterns on shirts would be more likely to hide excess weight. There are all kinds of long-sleeve shirts that are more formal than polo shirts and don't call for a layer above them. It's probably easier to mention some to avoid, such as black shirts and shirts with prominent pockets.

A plaid or windowpane tailored jacket would be useful for less-than-suit dress-up situations without being a blue blazer.

A v-neck sweater with a smooth 'hand' in for example solid blue is always an option in cooler weather to help achieve a moderately dressy look.
 

TheIronDandy

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A first question would be what kind of weather you're likely to be dealing with? If you're re-locating to Chicago you'll need heavy wool at the very least, if you're re-locating to Florida you need linen and silk.

I think the best advice I can give is: embrace your age (and your physique). It's very easy to fall into the trap of not wanting to look "like an old man", but lets face it: once your hair starts to grey (or go away), wrinkles around the eyes starts to show when you laugh, and you're built like Ed, you DO look "like an old man". Own it. There's nothing sadder than a grown man trying to dress in the slim fit, low cut, too tight trousers and jackets that fashion brands have been pushing for years. Sneakers and designer jeans doesn't make anyone look younger, it just highlights the discrepancy between an aging body and the fitness models those clothes were designed for. It's better to look like a stylish college professor (I know, no college professors wear sport coats these days...) than a failed Mick Jagger wannabee.

Second piece of advice would be to not worry too much about repeating yourself. If you wear things that fit you well, you're already doing better than most. You don't have to worry about varying your belt or shoes if your core wardrobe is solid. I would suggest sticking to a simple palette of a few colors that work well together - that way you can combine more of your pieces to create some variety in your outfits.

Consider that it might be advisable to invest more in odd trousers and sport coats, rather than suits. Unless you're in an industry where suits are required, the sport coat and wool trousers combo is sharp enough for most situations. A couple of tweed jackets (maybe one navy and one grey or brown herringbone) and grey flannels will be presentable without being overly formal, and it makes it easier to mix things up (you can wear the same jacket with different trousers and shirts to create some variety for a 2-day event, for example).

In the spirit of the advice above, consider if you really need classic "business shirts" (usually white, shiny poplin). While those shirts look great with business suits, they can easily look out of place with smart-casual outfits. Again, avoid the "sales-bro" look of business shirt (unbuttoned, no tie), designer jeans, sneakers and a blazer. Look into slightly coarser shirt fabrics, like the forum favourite the oxford cloth.

With the above things in mind, I put together a (very rough) example of what this could look like (trying to stay clear of the "insurance salesman" and "bro dad" looks). You could easily expand on the pieces you find yourself wearing the most (for example, getting more tweed jackets and flannel trousers if you find that works best for you).

1 tweed overcoat (navy or grey).
1 navy 2-piece suit. Worsted wool.
1 brown tweed jacket.
1 tobacco linnen jacket.
1 pair of grey flannel trousers.
1 pair of tan cavalry twill trousers.
1 pair of grey fresco trousers.
1 pair of cream linen trousers.
1 pair of khaki chinos.
2 white oxford shirts (probably button down).
1 striped oxford shirt.
1 indigo denim shirt.
2 white poplin shirts (if you need to do an overnight formal event - you can wear the same suit for two days in a pinch, but you want an extra shirt).
1 pale cashmere crewneck.
1 medium brown wool crewneck.
1 pair of DARK brown oxford shoes (your formal shoes for the suit).
1 pair of medium brown derby shoes.
1 pair of dark brown tassel loafers.
1 pair of medium brown suede penny loafers.
1 pair of dark brown suede chukka boots.
Dark brown leather belt.
Medium brown suede leather belt.

If you only wear a suit a few times a year, one suit should be fine (maybe get an extra pair of trousers, since trousers wear out faster). The jackets mean you have something to wear both in colder and hotter weather - the flannel and cavalry twill are heavier, cold weather fabrics while the linen and fresco are for warmer weather (though fresco can be worn in anything but freezing temperatures). A pair of khaki chinos are among the most flexible trousers you can wear: just make sure they actually fit!

The shirts mean you can wear a shirt for every day of the work week and still have one to spare; I'm not super keen on the poplin myself, but they work with the suit and can work with the jacket+trousers look as well. If you'll be in warm weather a lot, you might want to go for linen shirts instead. The sweaters can be worn with everything, and chinos-oxford/denim shirt-sweater is smart-casual without being bro-dad.

Shoes are geared towards casual tailoring. Oxfords easily look "off" with more casual outfits, and black shoes really only go with very formal outfits (some advanced dressers will wear black with casual tailoring, but I don't suggest starting with it). Loafers and derbies are still way dressier than what most people wear today.
 

Shotgunner

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Linen pants, corduroy pants, and moleskin pants would help avoid some of the archetypes you mention.

Patterns on shirts would be more likely to hide excess weight. There are all kinds of long-sleeve shirts that are more formal than polo shirts and don't call for a layer above them. It's probably easier to mention some to avoid, such as black shirts and shirts with prominent pockets.

A plaid or windowpane tailored jacket would be useful for less-than-suit dress-up situations without being a blue blazer.

A v-neck sweater with a smooth 'hand' in for example solid blue is always an option in cooler weather to help achieve a moderately dressy look.

Thanks!!!
 

Shotgunner

New Member
Joined
Oct 12, 2022
Messages
4
Reaction score
1
A first question would be what kind of weather you're likely to be dealing with? If you're re-locating to Chicago you'll need heavy wool at the very least, if you're re-locating to Florida you need linen and silk.

I think the best advice I can give is: embrace your age (and your physique). It's very easy to fall into the trap of not wanting to look "like an old man", but lets face it: once your hair starts to grey (or go away), wrinkles around the eyes starts to show when you laugh, and you're built like Ed, you DO look "like an old man". Own it. There's nothing sadder than a grown man trying to dress in the slim fit, low cut, too tight trousers and jackets that fashion brands have been pushing for years. Sneakers and designer jeans doesn't make anyone look younger, it just highlights the discrepancy between an aging body and the fitness models those clothes were designed for. It's better to look like a stylish college professor (I know, no college professors wear sport coats these days...) than a failed Mick Jagger wannabee.

Second piece of advice would be to not worry too much about repeating yourself. If you wear things that fit you well, you're already doing better than most. You don't have to worry about varying your belt or shoes if your core wardrobe is solid. I would suggest sticking to a simple palette of a few colors that work well together - that way you can combine more of your pieces to create some variety in your outfits.

Consider that it might be advisable to invest more in odd trousers and sport coats, rather than suits. Unless you're in an industry where suits are required, the sport coat and wool trousers combo is sharp enough for most situations. A couple of tweed jackets (maybe one navy and one grey or brown herringbone) and grey flannels will be presentable without being overly formal, and it makes it easier to mix things up (you can wear the same jacket with different trousers and shirts to create some variety for a 2-day event, for example).

In the spirit of the advice above, consider if you really need classic "business shirts" (usually white, shiny poplin). While those shirts look great with business suits, they can easily look out of place with smart-casual outfits. Again, avoid the "sales-bro" look of business shirt (unbuttoned, no tie), designer jeans, sneakers and a blazer. Look into slightly coarser shirt fabrics, like the forum favourite the oxford cloth.

With the above things in mind, I put together a (very rough) example of what this could look like (trying to stay clear of the "insurance salesman" and "bro dad" looks). You could easily expand on the pieces you find yourself wearing the most (for example, getting more tweed jackets and flannel trousers if you find that works best for you).

1 tweed overcoat (navy or grey).
1 navy 2-piece suit. Worsted wool.
1 brown tweed jacket.
1 tobacco linnen jacket.
1 pair of grey flannel trousers.
1 pair of tan cavalry twill trousers.
1 pair of grey fresco trousers.
1 pair of cream linen trousers.
1 pair of khaki chinos.
2 white oxford shirts (probably button down).
1 striped oxford shirt.
1 indigo denim shirt.
2 white poplin shirts (if you need to do an overnight formal event - you can wear the same suit for two days in a pinch, but you want an extra shirt).
1 pale cashmere crewneck.
1 medium brown wool crewneck.
1 pair of DARK brown oxford shoes (your formal shoes for the suit).
1 pair of medium brown derby shoes.
1 pair of dark brown tassel loafers.
1 pair of medium brown suede penny loafers.
1 pair of dark brown suede chukka boots.
Dark brown leather belt.
Medium brown suede leather belt.

If you only wear a suit a few times a year, one suit should be fine (maybe get an extra pair of trousers, since trousers wear out faster). The jackets mean you have something to wear both in colder and hotter weather - the flannel and cavalry twill are heavier, cold weather fabrics while the linen and fresco are for warmer weather (though fresco can be worn in anything but freezing temperatures). A pair of khaki chinos are among the most flexible trousers you can wear: just make sure they actually fit!

The shirts mean you can wear a shirt for every day of the work week and still have one to spare; I'm not super keen on the poplin myself, but they work with the suit and can work with the jacket+trousers look as well. If you'll be in warm weather a lot, you might want to go for linen shirts instead. The sweaters can be worn with everything, and chinos-oxford/denim shirt-sweater is smart-casual without being bro-dad.

Shoes are geared towards casual tailoring. Oxfords easily look "off" with more casual outfits, and black shoes really only go with very formal outfits (some advanced dressers will wear black with casual tailoring, but I don't suggest starting with it). Loafers and derbies are still way dressier than what most people wear today.
Thank you VERY much! That's exactly what I was hoping to read, in terms of a reply! I know my original posts were wordy, but you really keyed in on what I was looking for. Absolutely nailed it in terms of the wardrobe fitting the lifestyle.

You've given me a lot to work with here, and it's snowballing into more and more reading and researching, in a good way. Googling some examples of the items above, it then leads me down a lot of other, productive rabbit-holes of product websites, images, blogs, other forum posts, etc.

No specific plans to relocate yet, but certainly not hotter or more humid than my current latitude. This time of year, upstate NY or upper New England is a favorite getaway. But I still want some versatility in case work or vacation travel takes me down South.

Thanks again!!!!!
 

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