I am well aware that most guys don’t wear jackets and ties most of the time, if at all. But that’s not the point of this site and not the message I proclaim. I simply want more people to dress with intent, as a way of bringing elegance and appreciation of quality into our lives. Not wearing a jacket and tie does not mean abandoning elegance (because, after all, simply wearing a jacket and tie doesn’t make you elegant). I myself have lately been dressing more casually and thus put a lot of thought into how to do casual better.
V-neck undershirts
Wearing an open-collar shirt is fine by me, although I prefer filling the gap with an ascot. However, the shirt needs to have a well-built collar that stands on its own and opens well. If you are going to wear an undershirt when open-collared, as I do, get some v-neck versions. Otherwise that little flash of white that comes from a crew neck shirt, that I so often see at men’s necks, looks sloppy (it is underwear, after all) and distracts from where I should be looking, at your face.
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Upgrade your sweaters
Layering is a great way to add colour and texture to an outfit, not to mention warmth. But poor quality knitwear can ruin an otherwise excellent ensemble. Sweaters that are oversized, stretched out, pilling badly or just plain ill-fitting should be saved for housework or recycling. A fine sweater will look good and last a long time. Be it a cardigan, crew or v-neck, look for something that compliments your wardrobe and sits close to the body, without being tight, so you can layer if need be.
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Invest in a good sport jacket
There is such a thing as a casual sport jacket. In fact, “casual” is in the name: sport jackets were created for shooting and riding, not formal events. And there are features that will make a sport jacket feel even more casual, like soft, natural shoulders, patch pockets and patterns or textures. And that’s the kind of jacket you can wear with casual trousers, without a tie, even over a sweater.
Get a better belt (and take care of it)
I have been guilty of this myself in the past: having only one belt and wearing it into the ground. Instead, I now have several and regularly condition the leather ones, never wearing them two days in a row. A variety also helps when building an outfit: a woven leather belt looks casual but with a dressy touch, while a simple leather belt, if clean and high quality, adds a touch of sharpness to your waist.
Hem your trousers
Do I even have to explain this? If your pants are so long they bunch up at your ankles, take them to one of the dozens of alterations tailors, seamstresses or dry cleaners in your neighbourhood and have them shortened. Now. (See this precious article for length suggestions).
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Hosiery is often overlooked and that is a shame because a flash of colour or pattern at the ankle can do a lot to polish off an outfit. A flash of bunched up material and leg, on the other hand, can destroy an outfit. I have written an entire piece devoted to upgrading your socks, with some recommended brands and shops.
Look after your shoes
Casual shoes, whether they are chukkas, loafers or even canvas sneakers, still need the tender loving care you’d give to your fine oxfords. You probably don’t want to bother with a high gloss finish, but regular cleaning and moisturising will have the same effect on your casual outfits as it does on your tailored: to make you look a bit more put together. I have a whole article devoted to shoe care as well.
And the one bit of guidance that applies to all of the above, plus any other part of your wardrobe, is to invest in quality and fit. Buy the best you can afford (buy less if you need to make it possible) and insure the fit is exceptional.
Thanks for writing this, Pedro. Often style is portrayed as something to be bought – but of course, we all know the best things in life are free (or close to it).
Wearing a white crew neck t-shirt under a collared shirt is the most bush-league thing on the planet. Additionally, it’s something I once did myself fresh out of school! It makes me cringe to see this on Bay Street now (and also when my other half watched “NCIS”, the character Agent Gibbs does this and it drives me crazy!).
Re: texturing, I also agree – one of the best inexpensive upgrades I made was to buy some textured, solid color grenadine ties which add interest in an understated way.
Re: blazers – you really only need one, and make sure it fits nice and slim!
Re: hemming your trousers, again this is a lot cost upgrade (or no cost if you’re handy) that makes all the difference. Stores like Uniqlo sell cheap chinos and will hem them for free, so they end up looking much better than more expensive trou that puddles at the ankle.
Re: socks…well, in this case I admit to buying the same navy and grey McGregor ones from The Bay.
I’m very glad to hear you are interested, Brandon, but this is a huge question and not one I can easily and quickly answer. However, I would caution against thinking only about stores and instead focus on what kind of wardrobe do you want to build, what pieces do you need to get started, and how much are you able to invest? Try to find items of quality that will last and are moderately cut (neither too fashionable nor too unfashionable). And spend as much as you are able – it is better to have one excellent suit than three poor suits. However, dressing well does not necessarily mean suits – I think having a couple of jackets (a navy blazer and a sport jacket) plus a few pairs of trousers (grey flannel, chinos) will be much more versatile. Plus, don’t forget, several high quality shirts. And at least two pairs of quality shoes. I’d say focus on that before thinking about suits. The other issue with stores is that it depends on your local area, of course. For that, you will have to do some investigating on foot. Best of luck!
When I was in this situation 6 years ago (has it been that long?!), I started with a plain navy suit from Benjamin: http://ehaberdasher.com/index.php/clothing/suits.html
I got comfortable with the product on Styleforum and ordered it online back when CAD was at par with USD. Since then, I’ve added 2 more suits and sport jackets and am happy.
If I were doing the same thing today, I would go to Spier and Mackay on Toronto Street. I would suggest getting just one suit in plain navy and wear it for 6 months or so. If you’re happy, repeat with a plain grey.
5 Comments
Viator
February 10, 2017 at 3:03 pm
416expat
February 13, 2017 at 3:13 pm
Brandon
February 18, 2017 at 2:21 am
Pedro Mendes
February 18, 2017 at 10:57 am
416expat
February 21, 2017 at 11:06 am
Very helpful as ever.
Thanks for writing this, Pedro. Often style is portrayed as something to be bought – but of course, we all know the best things in life are free (or close to it).
Wearing a white crew neck t-shirt under a collared shirt is the most bush-league thing on the planet. Additionally, it’s something I once did myself fresh out of school! It makes me cringe to see this on Bay Street now (and also when my other half watched “NCIS”, the character Agent Gibbs does this and it drives me crazy!).
Re: texturing, I also agree – one of the best inexpensive upgrades I made was to buy some textured, solid color grenadine ties which add interest in an understated way.
Re: blazers – you really only need one, and make sure it fits nice and slim!
Re: hemming your trousers, again this is a lot cost upgrade (or no cost if you’re handy) that makes all the difference. Stores like Uniqlo sell cheap chinos and will hem them for free, so they end up looking much better than more expensive trou that puddles at the ankle.
Re: socks…well, in this case I admit to buying the same navy and grey McGregor ones from The Bay.
Sir what stores do you recommend for suits and other clothing? Im 25 and want to start dressing well. I am looking for suits below $800.
I’m very glad to hear you are interested, Brandon, but this is a huge question and not one I can easily and quickly answer. However, I would caution against thinking only about stores and instead focus on what kind of wardrobe do you want to build, what pieces do you need to get started, and how much are you able to invest? Try to find items of quality that will last and are moderately cut (neither too fashionable nor too unfashionable). And spend as much as you are able – it is better to have one excellent suit than three poor suits. However, dressing well does not necessarily mean suits – I think having a couple of jackets (a navy blazer and a sport jacket) plus a few pairs of trousers (grey flannel, chinos) will be much more versatile. Plus, don’t forget, several high quality shirts. And at least two pairs of quality shoes. I’d say focus on that before thinking about suits. The other issue with stores is that it depends on your local area, of course. For that, you will have to do some investigating on foot. Best of luck!
When I was in this situation 6 years ago (has it been that long?!), I started with a plain navy suit from Benjamin: http://ehaberdasher.com/index.php/clothing/suits.html
I got comfortable with the product on Styleforum and ordered it online back when CAD was at par with USD. Since then, I’ve added 2 more suits and sport jackets and am happy.
If I were doing the same thing today, I would go to Spier and Mackay on Toronto Street. I would suggest getting just one suit in plain navy and wear it for 6 months or so. If you’re happy, repeat with a plain grey.