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Discussion Starter · #1 ·
I work in a very casual office where most men are in t-shirts and sneakers, and I'm finding it really hard to dress well while still fitting in, so I end up dressing almost as casual as the other guys. Not just at work, but while doing other casual activities such as going out with friends and similar stuff. I've asked something similar a while ago, but realized that the look I was going for might be a bit overkill for daily casual attire. Basically I decided to skip the dress slacks and sport coats in favor of jeans, chinos, and more casual jacket styles.

However, I've decided to keep the button ups and dress shoes. But then I thought about it again, and honestly I'm kind of lost. I want to dress well but at the same time don't want to end up excluding myself from society in the process. I'm not sure if a button up tucked into jeans or chinos with dress shoes would be overdressed in the situations I've mentioned above, or would fit in just fine while looking well dressed and well put together.

The dress shoe styles I'm talking about and that I'm mostly interested in are wingtip derbies (I initially wanted oxfords but decided to go with derbies for their more casual nature), monk straps and loafers, for the most part. Not sure what other styles would be on the more casual side of dress shoes than these. I love how dress shoes make me look when wearing them. I think they fit my personality and body type very well and make me look more mature as opposed to when wearing sneakers, which in all honesty don't seem to be doing much to make me look good.

With all that said though, I surely don't want to end up looking too out of place in situations where other guys are dressed ultra casual (again, t-shirts, jeans and sneakers). I consider dress shoes incredibly stylish and much better than sneakers even in casual settings (of course I wouldn't wear them to the gym or the beach, but you get the idea), but I'm going to accept it if it's indeed inappropriate to wear the shoe styles I've mentioned in a casual environment. If it's ok to wear such shoes casually, it would be great, but if not, I would appreciate suggestions for other options suited for summer. Also, I'm 26 if this makes a difference.
 

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I wear dress shoes with casual-smart clothing frequently in the office and with casual clothes out of the office. I'm the most smartly dressed guy at work and therefore look out of place. Don't care. I still manage to get on well with others.
 

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My advice would be to avoid a business look. So your chinos should be slim, if you have the body for it, with no pleats, cuffs, or crease.

Your button downs should preferably be patterned but avoid stripes. If you do go with stripes or solids tone down the level of dress on everything else. Polo shirts are a good option as well.

For shoes if you are not going to go for something really casual like boat shoes I would recommend suede whether as shoes or boots but without brouging as they are more casual then calf leather. If you want to wear calf leather wingtip derbys then you can tone down the outfit with jeans and a polo or patterned button down.

The idea is to avoid a white collor look. As a recent trad forum post pointed out wearing a blue OCBD, surcingle belt, khakis, and penny loafers anywhere outside of an office building or fancy restaurant is going to make you stand out.

My general philosophy is to have one item that is associated with being dressy per outfit.

This all of course is dependent of your comfort level if you are comfortable wearing a blue OCBD, khakis, and burgundy wingtip derbys then go for it. But your post seems to say you are not so my answers are tailored to that.
 

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Discussion Starter · #5 ·
My advice would be to avoid a business look. So your chinos should be slim, if you have the body for it, with no pleats, cuffs, or crease.

Your button downs should preferably be patterned but avoid stripes. If you do go with stripes or solids tone down the level of dress on everything else. Polo shirts are a good option as well.

For shoes if you are not going to go for something really casual like boat shoes I would recommend suede whether as shoes or boots but without brouging as they are more casual then calf leather. If you want to wear calf leather wingtip derbys then you can tone down the outfit with jeans and a polo or patterned button down.

The idea is to avoid a white collor look. As a recent trad forum post pointed out wearing a blue OCBD, surcingle belt, khakis, and penny loafers anywhere outside of an office building or fancy restaurant is going to make you stand out.

My general philosophy is to have one item that is associated with being dressy per outfit.

This all of course is dependent of your comfort level if you are comfortable wearing a blue OCBD, khakis, and burgundy wingtip derbys then go for it. But your post seems to say you are not so my answers are tailored to that.
I'm not comfortable dressing this way because I'm not used to it. Also because I got told that my chukka boots are for weddings and similar comments about my more "dressy" clothes (casual untucked button up, dark jeans and chinos).

I'm asking whether it's ok and acceptable to dress this way even when the situation is casual. I've seen posts on this forum that say "leather dress shoes are real men's shoes and that's what men should wear." I logically thought that leather shoes are the way to go since I started caring about the way I dress, thus started with chukka boots and thought the next step is dress shoes.

Would it be acceptable to be wearing dress shoes in casual settings? If not, what else would you suggest that would make me stand out in a casual way? Something tells me it's not sneakers but what other choices do I really have? What about options for shirts? I'm not sure about t-shirts since I don't believe they're for everyone (they don't compliment every body type and certainly not mine), so what other choices am I left with really? I guess what I'm asking is, regardless of how I feel about it or if I'm comfortable with it, is it preferable that I go the dressy way or the more casual way if I want to stand out as a well dressed person in a good way? What clothing should I look at of it's the casual way? Again I'm talking about strictly casual settings here (apart from the obvious ultra causal ones like the gym, the beach... etc), not special occasions or anything like that.
 

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Discussion Starter · #6 ·
I wear dress shoes with casual-smart clothing frequently in the office and with casual clothes out of the office. I'm the most smartly dressed guy at work and therefore look out of place. Don't care. I still manage to get on well with others.
How do you feel about it? Do you ever feel too out of place when literally ever other guy is in sneakers and very casual clothing? I'm torn between dressing at their level just to fit in or dressing a step above because I like dress shoes.
 

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Discussion Starter · #7 ·
For summer I like loafers especially in suede. They can look quite appropriate with most clothing. Even a summer suit (something in linen/linen blend/seersucker) may work well.
But you can't wear only loafers everyday, I would have liked to have some variety. What other shoes do you like to wear for casual occasions?
 

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Would it be acceptable to be wearing dress shoes in casual settings?
Yes it is perfectly acceptable to wear dress shoes in a casual setting as long as they are not black.

If not, what else would you suggest that would make me stand out in a casual way? Something tells me it's not sneakers but what other choices do I really have?
Several options suede shoes, boat shoes, leather work boots such as Red Wing Iron Ranger boots, canvas sneakers, and leather sneakers come to mind.

What about options for shirts? I'm not sure about t-shirts since I don't believe they're for everyone (they don't compliment every body type and certainly not mine), so what other choices am I left with really?
Polo shirts, popover shirts, patterned button front shirts, non business colored solid button front such as pink. If you want something without a collar a henley is nice since it is thicker than a t shirt.

I guess what I'm asking is, regardless of how I feel about it or if I'm comfortable with it, is it preferable that I go the dressy way or the more casual way if I want to stand out as a well dressed person in a good way? What clothing should I look at of it's the casual way? Again I'm talking about strictly casual settings here (apart from the obvious ultra causal ones like the gym, the beach... etc), not special occasions or anything like that.
Here is the thing none of us can answer these questions for you, you have to decide what you want to do. Personally I think both casual and dressy clothing can look good. Maybe think about why you want to dress up/dress better and also see which style of clothing you are attracted to.
 

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Discussion Starter · #10 ·
@AmirF27 I've lost patience with you. I rarely said this, but you're overthinking this. You're not ready; just wear what everybody around you wears. I'd love to guide you, but an online forum is not the best place.
Lol, I've lost count of the times people have told me they lost patience with me. I'm terribly sorry, I truly am. I don't mean it, it's just that I'm truly not sure what to do.
 

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Other people really don't look at you as closely or as critically as you may think they do. When it comes to your shoes, wear the pair you enjoy and that are most comfortable on your feet. The options under consideration that you have mentioned in your OP all sound fine to me. You will be fine. :cool:
 

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Other people really don't look at you as closely or as critically as you may think they do.
Yes!

When it comes to your shoes, wear the pair you enjoy and that are most comfortable on your feet.
Yes!

The options under consideration that you have mentioned in your OP all sound fine to me.
Yes!

You will be fine.
No comment.

********

Amir: Whoever told you that chukka boots are only for weddings is a knucklehead. Get some and wear them with your casual clothes. Make them a regular part of your rotation.

And practice standing up straight, squaring your shoulders, and saying, "Thanks, but this is how I like to dress." Do not post anything further until you have practiced that 10 times.
 

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This is unrelated to fashion, but if you dress above the others and are not confident in it, your body language and everything about you will be "off" when you relate to others.

Unless you are completely self-confident, you will be better off dressing as the others or only a bit above what they are doing.

Remember, life is always more important than what you are wearing - - especially if what you are wearing (that others are not) undermines your self confidence.
 

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I'm not comfortable dressing this way because I'm not used to it. Also because I got told that my chukka boots are for weddings and similar comments about my more "dressy" clothes (casual untucked button up, dark jeans and chinos).

I'm asking whether it's ok and acceptable to dress this way even when the situation is casual. I've seen posts on this forum that say "leather dress shoes are real men's shoes and that's what men should wear." I logically thought that leather shoes are the way to go since I started caring about the way I dress, thus started with chukka boots and thought the next step is dress shoes.

Would it be acceptable to be wearing dress shoes in casual settings? If not, what else would you suggest that would make me stand out in a casual way? Something tells me it's not sneakers but what other choices do I really have? What about options for shirts? I'm not sure about t-shirts since I don't believe they're for everyone (they don't compliment every body type and certainly not mine), so what other choices am I left with really? I guess what I'm asking is, regardless of how I feel about it or if I'm comfortable with it, is it preferable that I go the dressy way or the more casual way if I want to stand out as a well dressed person in a good way? What clothing should I look at of it's the casual way? Again I'm talking about strictly casual settings here (apart from the obvious ultra causal ones like the gym, the beach... etc), not special occasions or anything like that.
Ignore what someone said about Chukkas. That's dead wrong. Chukkas are pretty much the perfect shoe/boot for what you're looking to do.

If you're not overweight at all, nice slim chukkas (NOT skinny fit), some kind of slim fit patterned button down shirt (preferably with button down collar), sleeves rolled up on your forearms, and chukkas would be a nice dressed up casual look.

Same if you are overweight really, just adjust the cuts of the clothing accordingly. Always match clothing to body type. Skinny guys in baggy clothes look just as bad as heftier guys in tight clothes.
 

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But you can't wear only loafers everyday, I would have liked to have some variety. What other shoes do you like to wear for casual occasions?
If you're not interested in adding more loafers to your wardrobe, this is just a sampling of the many styles that are really only suitable for casual wear, IMO.

Edit: Do you like boots?

 

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If you're not interested in adding more loafers to your wardrobe, this is just a sampling of the many styles that are really only suitable for casual wear, IMO.

Edit: Do you like boots?

If my memory serves me well this AM, I recall you had ordered a pair of those kidney hued and Ridgeway soled Brogues. Have you received them and how are they working out for you? It seems every time I see them, I am destined to endure several days of indecisive angst! :(
 

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Yes!

Yes!

Yes!

No comment.

********

Amir: Whoever told you that chukka boots are only for weddings is a knucklehead. Get some and wear them with your casual clothes. Make them a regular part of your rotation.

And practice standing up straight, squaring your shoulders, and saying, "Thanks, but this is how I like to dress." Do not post anything further until you have practiced that 10 times.
Agreed, and Amir should keep in mind that the know-it-all knucklehead probably doesn't even know what a chukka boot is.
 

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If my memory serves me well this AM, I recall you had ordered a pair of those kidney hued and Ridgeway soled Brogues. Have you received them and how are they working out for you? It seems every time I see them, I am destined to endure several days of indecisive angst! :(
Actually, I had purchased a different model in the same hide.



The one I purchased was named the Reggie (Really dumb name!) directly above, but it is now discontinued. As you can see the hide is the same, but it's a PTB rather than a brogue, and it has a softer EVA sole rather than the Ridgeway. Haven't had a Ridgeway sole, but understand it's similar to Dainite in both wear and comfort, and I like the one pair of Dainite soled footwear I have very well.

Both shoes are built on the same Sanders last, M265L, which is a broader last somewhat equivalent to a U.S. D+ or E and offers a roomy fit for my D width feet. And it also has a higher and roomy toe box. I find them most comfortable with socks that aren't too thin. I size down one full size in UK sizes, and Sanders' sizing is consistent with this practice.

The grained hide is embossed/rolled cowhide, as is almost all grained cowhide, and is therefore technically corrected grain cowhide. It's not stiff, but obviously not as soft as calf. They're fully leather lined with thick, soft vegetable tanned leather. While the pair above aren't mine, it offers an idea of the quality of production, which blew me away for a comparatively inexpensive pair of shoes.

The shoes I have are sturdy, handsome (IMO) comfortable and very well made. The color harmony between the hide, extended natural welt and red sole are what closed the deal for me, and these shoes have received more compliments than possibly any other footwear, despite the bold and somewhat bumptious aesthetic. The toes even take a nice shine.

Of the two different models, I think the brogue is probably the more handsome as the brogue design optimizes the appearance of the hide, and I like the idea of the Ridgeway sole which is much more durable than EVA.
 
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