What can I wear with shorts other than sneakers or loafers?

[jeremygo]

Birkenstocks were "fancy"/"expensive" shoes to me growing up. I was chatting with a friend once who mentioned his college had a black tie event every year, which blew my mind as the most formal my college got was "tie dye discouraged." Now I'm a city boy and keep those birks on standby for trips back to the country.

Anyhow, a few pairs have stood out to me as I've been looking around for casual summer shoes:

- Paraboot boat shoes look nice (more refined than your average pair of Sperrys): https://sonofastag.com/products/paraboot-malo-raid-shoe-brown-lis-america

- Jacque Soloviere Oliviers (a bit more elegant but could still go with shorts I think, they also have similar options with heavier rubber soles if you're doing a lot of walking):

OLIVIER NUT SUEDE

Made in Italy, Olivier's derby shoes are great for adding a touch of refinement to your casual wardrobe. Constructed using a flexible and lightweight welt, this pair is made from smooth suede and fitted with comfortable rubber soles to support your feet throughout the day. Inspired by a Belgian...

jacquessoloviereparis.com

 

[Sinyo18]

Birkenstocks were "fancy"/"expensive" shoes to me growing up. I was chatting with a friend once who mentioned his college had a black tie event every year, which blew my mind as the most formal my college got was "tie dye discouraged." Now I'm a city boy and keep those birks on standby for trips back to the country.

Anyhow, a few pairs have stood out to me as I've been looking around for casual summer shoes:

- Paraboot boat shoes look nice (more refined than your average pair of Sperrys): https://sonofastag.com/products/paraboot-malo-raid-shoe-brown-lis-america

- Jacque Soloviere Oliviers (a bit more elegant but could still go with shorts I think, they also have similar options with heavier rubber soles if you're doing a lot of walking):

OLIVIER NUT SUEDE

Made in Italy, Olivier's derby shoes are great for adding a touch of refinement to your casual wardrobe. Constructed using a flexible and lightweight welt, this pair is made from smooth suede and fitted with comfortable rubber soles to support your feet throughout the day. Inspired by a Belgian...

jacquessoloviereparis.com

In my experience Paraboot is an excellent company, high quality footwear.

 

[rjc149]

We are already taking a step down in elegance by choosing comfort (shorts) over style (pants), so I think it's precisely for that reason why we should to try to regain ground by focusing on what else we are wearing. The amount of effort is subjective of course, but I don't consider opting for a collared shirt instead of a t-shirt, and loafers instead of sneakers too much.

Take this photo for example. Casual, dressed for the heat, but still representable. He looks like a man with a plan. Switch the shirt for a t-shirt and shoes for sneakers, and you have someone who looks like they just rolled out of bed.

View attachment 2184297

To me, this is a similar concept to sneakers with suits, or those hybrid dress shoes / sneakers you see everywhere these days -- oxford upper, sneaker sole. By committing to neither aesthetic, it succeeds in neither, and the amalgam of the two becomes something separate entirely -- not a dressy sneaker nor an athletic oxford, but a "frankenshoe." Even leather court sneakers going by the monicker "dress sneakers" these days, which are decidedly sneakers, are an abomination to my eyes when worn with slacks or suits.

This young man exhibits a similar level of indecision and prevarication on exactly how he's trying to dress. Is he trying to be casual? Is he trying to be dressy? Rather than incorporating both elements for a "dressy summer casual" as he would probably like to believe, he is actually committing to neither aesthetic, and is therefore neither. Not both. He is something else entirely. Not casual, not dressy, but a "douchebag finance bro waiting for his coke dealer before heading off to the Hamptons."

If you're going to wear shorts, you must embrace the ultra-casualness of shorts. You have to make that decision and commit to it. You have to own it and be comfortable in it. To me, there's an element of self-consciousness and self-scrutiny that comes with trying to elevate an outfit that incorporates shorts -- like you're trying to be something you're not.

I say it's perfectly, 100% okay to be not be dressy sometimes. It's preferable, even. When I see a man I consider to be impeccably dressed loafing around in shorts and New Balance sneakers at a summer barbeque, he is humanized in my eyes. There is inherent charm and dignity in humanity.

 

[jko]

This young man exhibits a similar level of indecision and prevarication on exactly how he's trying to dress. Is he trying to be casual? Is he trying to be dressy? Rather than incorporating both elements for a "dressy summer casual" as he would probably like to believe, he is actually committing to neither aesthetic, and is therefore neither. Not both. He is something else entirely. Not casual, not dressy, but a "douchebag finance bro waiting for his coke dealer before heading off to the Hamptons."

If this man was wearing the same outfit but chinos instead of shorts, would you still feel this way? Does the mere appearance of shorts label the whole outfit so casual, that wearing a collared shirt is jarring?

I understand your viewpoint, but disagree, as I don't think dressy and casual are mutually exclusive.

I say it's perfectly, 100% okay to be not be dressy sometimes.

This I agree with. The issue I'm having is that once the temperature hits the 20s, I see too many men in shorts, worn out t-shirts, and sneakers that should have been retired three summers ago. Fine in a backyard barbeque, not so in the city centre, stores, or restaurants.

I'd rather see someone dressed as the man in the photo. Elevated. To me, that is humanizing.

(I'd rather see them dressed this way in a barbeque as well, but whatever.)

 

[breakaway01]

If this man was wearing the same outfit but chinos instead of shorts, would you still feel this way? Does the mere appearance of shorts label the whole outfit so casual, that wearing a collared shirt is jarring?

I understand your viewpoint, but disagree, as I don't think dressy and casual are mutually exclusive.


This I agree with. The issue I'm having is that once the temperature hits the 20s, I see too many men in shorts, worn out t-shirts, and sneakers that should have been retired three summers ago. Fine in a backyard barbeque, not so in the city centre, stores, or restaurants.

I'd rather see someone dressed as the man in the photo. Elevated. To me, that is humanizing.

(I'd rather see them dressed this way in a barbeque as well, but whatever.)

I'm totally OK with the OCBD and shorts look. Those shoes, not so much.

 

[rjc149]

Does the mere appearance of shorts label the whole outfit so casual, that wearing a collared shirt is jarring?

To put it simply, yes it does. Chinos or slacks would be congruent with this "dressy casual" or "business casual" aesthetic. Shorts are ultra-casual in my book, they're in the same category as sneakers, t-shirts, and baseball caps. I feel similarly about men trying to "dress up" jeans and t-shirts with dress shoes and sport coats, like a pickup artist or something.

If you choose to wear shorts, you should be comfortable presenting an ultra-casual look and not feel any desire to incorporate dressier elements to "elevate" it. Because when you do that, you're not improving a foundation, you're creating something entirely different and I don't think it's a good look.

Now, if you want to, that's a different story. If you enjoy the 'old money in shorts' look with a tucked-in OCBD, loafers, and shorts with cuffs and creases, then do it. But there should be no need to do any of that because "otherwise you're too casual." Shorts are casual. It's okay to go to the hilt being casual. Dressing it up doesn't make you look better. And this man in the photo, with his Instagram "half tuck," sockless dress shoes and one too many undone shirt buttons, I don't think he's well-dressed. I'd rather see him wearing sneakers and a plain t-shirt.

The issue I'm having is that once the temperature hits the 20s, I see too many men in shorts, worn out t-shirts, and sneakers that should have been retired three summers ago. Fine in a backyard barbeque, not so in the city centre, stores, or restaurants.

I agree, and to me, shorts are very time-and-place specific, but rather than applying an 'always/never" rubric, a man should know how to calibrate shorts to the given setting. A lot of men don't know how to, or don't bother to and I have to agree, that can be visually off-putting or even disrespectful. Generally speaking, when doing casual daytime activities in hot weather, shorts are good to go. If you plan to attend an evening dining venue and get the opportunity to change into long pants, you should do that unless the venue is ultra-casual.