What shoes am I still missing in my little collection?

[dieworkwear]

Yes, I def need those! To my understanding chukka boots are for the fall/winter?



I know exactly what you mean. When I started my shoe journey it became an addiction to have as many shoes possible without thinking about what I was trying to achieve. So this is how I ended up with 13 shoes from which I sold a few. The only one on the list are the cognac Santoni's I'm trying to get rid off and the cognac Francesco Benigno's.

These are the kinds of clothes I'm wearing now. most are from the summer that's why I'm wearing polos (don't mind the mask it is a photoshop lol):

View attachment 1488051

But im not "happy" with my style now. I'm aiming for the style Kirby Allison has. So that would be very formal.

My personal feeling is that shoes should be the foundation of your wardrobe, not the center. As is, your shoe wardrobe seems fine for how you dress now. If you wanted to add another pair, then I think a pair of suede chukkas could be useful. Dark pebble grain can also be useful for chukkas. I personally dislike smooth calf chukkas, as I think the design lends too much unbroken expanse without a textured leather such as suede or pebble grain.

When I look at your collection of shoes, I see too many oxfords given how you dress. I also think you have too many tan shoes. Both are harder to wear than plainer, more casual shoes in dark brown. I think people buy oxfords and tan shoes because they catch the eye when you're shopping. But in a classic men's style outfit, shoes are not meant to catch the eye. The focus is typically on the shirt, tie, and jacket combo, the V-shape under your chin. Incoherent shoes become distracting and draw the eye downwards.

If you're still developing the rest of your wardrobe, I would let your taste naturally evolve and see where it takes you. Buy shoes around your wardrobe and as the need arises.

 

[AdamBara]

But im not "happy" with my style now. I'm aiming for the style Kirby Allison has. So that would be very formal.

If I had to chose a style between Sven Raphael Schneider (clownish style, not personal) from the Gentlemen's Gazette or Kirby Allison (Social psychopath) from Kirby Allison, it's a Kirby Allison style I'm aiming for if that makes sense.

 

[Nobilis Animus]

Eh, I disagree.

You can't really dress down black oxfords very well, but you can dress up a pair of brown longwings.

No one would bat an eyelash if you wore one to a funeral or wedding.

OP already has a pair of dark brown oxfords for those occasions anyway.

Perhaps weddings are in fact more of a crapshoot, but what about black tie events?

I like to keep those more "casual" than some here, because I wear evening clothes fairly often in normal times, so I'll use things like velvet jackets, open-neck shirts, scarves, etc. I'd even go for combat boots, if you lean more edgy.

But they wouldn't be in brown. It just doesn't work as well.

 

[dieworkwear]

Perhaps weddings are in fact more of a crapshoot, but what about black tie events?

I like to keep those more "casual" than some here, because I wear evening clothes fairly often in normal times, so I'll use things like velvet jackets, open-neck shirts, scarves, etc. I'd even go for combat boots, if you lean more edgy.

But they wouldn't be in brown. It just doesn't work as well.

Seems like a bad idea to buy shoes with the idea that they can be worn for black tie, wedding events, with velvet jackets in the evening, and suits that the person doesn't already wear with any regularity. If someone attends black tie events with some regularity, then they should buy shoes for that lifestyle. But they shouldn't invent scenarios in their head to justify their purchases.

Most men don't live the kind of lifestyle, or have the kind of wardrobe, where a black oxford would be considered useful. I think most men dress pretty casually nowadays. Everyone needs a suit, but most people can get away with wearing derbies with that suit for events such as weddings and funerals. The rest of your shoe wardrobe should be centered on how you dress on a regular basis; not events that come up once every few years.

If by chance, the person's wardrobe develops in such a way that they wear suits often -- even if it's in a way that's more "dressed up" than others around them -- then they can get black oxfords. But the suits should come first; not the shoes.

 

[AdamBara]

 

[FlyingHorker]

Perhaps weddings are in fact more of a crapshoot, but what about black tie events?

I like to keep those more "casual" than some here, because I wear evening clothes fairly often in normal times, so I'll use things like velvet jackets, open-neck shirts, scarves, etc. I'd even go for combat boots, if you lean more edgy.

But they wouldn't be in brown. It just doesn't work as well.

I've personally never even had the opportunity for a black tie event.

At most weddings I don't even bother with a suit and usually wear a SC+trouser+tie combination.

 

[Phileas Fogg]

I’ve gone my entire professional career without a pair of black shoes. Of course, I’m not in a profession where business formal is ever required.

I might just buy some for the hell of it.

 

[Mercurio]

For a person of your age (and mine, that doubles yours), I would put black Oxfords at the bottom of the list: they would be used only in formal funerals or weddings, if so.

I agree with the chukka suggestion as they are a very versatile kind of footwear that can easily be matched with all kind of outfits, being able to dress up or down depending on your mood and garments.

I would look for a lot more boots, of every different kind, from dress to work boots: they can be Chelsea, derby cap toe, wingtips, jumpers, in calf, suede or more exotic leathers such as Cordovan or Kudu. My collection has slowly moved away from shoes to boots and I found that they are a very good option: you will find a lot of inspiration in the almost 1000 pages "boots, boots, boots" thread.

 

[dieworkwear]

One thing I like about suede chukkas is that they can be worn with a very wide range of outfits. So, as your taste evolves and your wardrobe expands in unexpected directions, your chukkas can still stay with you. You can also put on outfits and wear those chukkas in a way that allows you to judge the totality of the outfit. Sometimes, you may buy a jacket and wrongly think that it doesn't work for you, but only because you haven't tried it on in a full outfit.

Some very basic outfits where I think chukkas work. IMO, these are very basic classic menswear outfits that are a good starting place for fall/ winter wardrobes that don't center around a tailored jacket. Pair them with jeans, chinos, or trousers in fall/ winter fabrics (e.g. moleskin, cord, flannel).

As your taste develops, you can wear chukkas with something a little less basic, but still pretty "classic menswear."

They also work with fall tailoring, mostly casual and often sport coats. All of these are very chukka outfits

Certain chukkas, such as unlined chukkas or more wildly Sander's "Playboy chukkas," can also be worn in the springtime. Personally would opt for suede chukkas if seasonal variety is important to you. Pebble grain loos wrong to me in the spring/ summer months.

If you want to dress like Kirby, however, that basically means a tailored outfit (sport coats and suits). I think many guys want to wear suits all the time, but quickly find out it doesn't suit them or their lifestyle, so they end up dressing more casually over time. If you do want to wear tailoring, and at least sport coats, I would go for some kind of derby. I personally like split toes or at least apron derbies, but it's a matter of taste. A dark brown derby can be worn year-round with almost any kind of tailoring, including suits, whereas chukkas lean a bit more casual. I only suggest chukkas because I think many guys end up dressing more casually over time.

Many of the shoes in your collection look like they're not that versatile or useful in many tailored outfits. Your oxfords, for example, are only good with suits; the tan shoes mostly for lighter colored jackets. These are very specific situations. So if you want to wear suits and sport coats more often, I would get a pair of shoes that allows you to experiment in that specific area. Get a pair of derbies in dark brown, so that you can wear them across a wide range of styles (not just for specific events like black tie or weddings). Then use that pair as a foundation for your experimentation. Save the money you would have spent on subsequent shoe purchases for better tailored clothing, etc.

 

[Nobilis Animus]

Seems like a bad idea to buy shoes with the idea that they can be worn for black tie, wedding events, with velvet jackets in the evening, and suits that the person doesn't already wear with any regularity. If someone attends black tie events with some regularity, then they should buy shoes for that lifestyle. But they shouldn't invent scenarios in their head to justify their purchases.

Most men don't live the kind of lifestyle, or have the kind of wardrobe, where a black oxford would be considered useful. I think most men dress pretty casually nowadays. Everyone needs a suit, but most people can get away with wearing derbies with that suit for events such as weddings and funerals. The rest of your shoe wardrobe should be centered on how you dress on a regular basis; not events that come up once every few years.

If by chance, the person's wardrobe develops in such a way that they wear suits often -- even if it's in a way that's more "dressed up" than others around them -- then they can get black oxfords. But the suits should come first; not the shoes.

I've personally never even had the opportunity for a black tie event.

At most weddings I don't even bother with a suit and usually wear a SC+trouser+tie combination.

I’ve gone my entire professional career without a pair of black shoes. Of course, I’m not in a profession where business formal is ever required.

I might just buy some for the hell of it.

I have no doubt that the majority of people do not "need" black shoes. The type of events where they would actually be required - mostly because you'd end up wearing black trousers - are comparatively few.

From the OP's own posts though, it's clear he wants to start making his style more formal. I would suggest that black shoes are good starting point to that - perhaps black boots instead. I also agree that suede chukkas are a good shoe to have (I actually just got a compliment on mine yesterday afternoon).

On a regular basis, I tend towards something far more "smart casual" as a baseline. Dark suits or tailored clothes actually work for me, not just because of lifestyle, but also my own inclinations - which is far from a boring business combo. If the OP is going for something similar, he's going to need some more shoes.

 

[daizawaguy]

White shirt, Jeans and Black oxford....how classic could that be, and casual to boot. Often with browns, you get stuck in the various shades, and add lighter, darker, redder, etc.... Black and blue. Simple. Classic.

 

[dieworkwear]

White shirt, Jeans and Black oxford..

☹

 

[Nobilis Animus]

White shirt, Jeans and Black oxford....how classic could that be, and casual to boot. Often with browns, you get stuck in the various shades, and add lighter, darker, redder, etc.... Black and blue. Simple. Classic.

See, my inclination would be to pair that with black boots of some kind. Possibly jodhpurs.

That just shows the influence of personal style, but the colour combination is still solid.

 

[dieworkwear]

These combos don't make any sense to me. Where in classic men's dress are these combinations seen?

In the past, I've seen people here recommend black oxfords for business casual, jeans, sport coats, and all things that don't go with black oxfords.

If by "a white shirt and jeans" we mean a white dress shirt, I already think that looks bad. I suppose you can wear a white t-shirt, but then you'd at least need some kind of layer to finish off the look (a jacket or a sweater of some kind). At that point, your whole outfit is so casual, you need a casual shoe. If we're talking about a white OCBD, then you need a trad-y shoe. Not black jodhpurs.

@Phileas Fogg asked me in another thread whether I think brogueing matters in a black oxford. No, oxfords are for suits. If you're wearing a sport coat, you need something more casual, not oxfords.

Stuff like business casual (mentioned in another thread) is already kind of depressing because business casual is a somewhat depressing look. But when worn with black oxfords, it somehow becomes more depressing. Like the guy is yearning to dress better, and can only do this tiny little thing in his realm of power. Just wear a sport coat, and then wear shoes that are a little more casual than oxfords.

If someone wants to wear oxfords in this very internet-shoe-enthusiast way, they can, of course. People can dress however they want. But this is a new internet invention and not about classic men's dress.

See in these photos.

Derbies and other casual shoes: for suits and casual clothes
Oxfords: for suits

 

[Nobilis Animus]

These combos don't make any sense to me. What dress language are we using? What tradition are we drawing from? Where in classic men's dress is this seen?

In the past, I've seen people here recommend black oxfords for business casual, jeans, sport coats, and all things that don't go with black oxfords.

If by "a white shirt and jeans" we mean a white dress shirt, I already think that looks bad. I suppose you can wear a white t-shirt, but then you'd at least need some kind of layer to finish off the look (a jacket or a sweater of some kind). If we're talking about a white OCBD, then you need a trad-y shoe. Not black jodhpurs.

@Phileas Fogg asked me in another thread whether I think brogueing matters in a black oxford. No, oxfords are for suits. If you're wearing a sport coat, you need something more casual, not oxfords.

Stuff like business casual (mentioned in another thread) is already kind of depressing because business casual is a somewhat depressing look. But when worn with black oxfords, it somehow becomes more depressing. Like the guy is yearning to dress better, and can only do this tiny little thing in his realm of power. Just wear a sport coat, and then wear shoes that are a little more casual than oxfords.

If someone wants to wear oxfords in this very internet-shoe-enthusiast way, they can, of course. People can dress however they want. But this is a new internet invention and not about classic men's dress.

See in these photos.

Derbies and other casual shoes: for suits and casual clothes
Oxfords: for suits

Before I reply, I think it's important to point out that I'm just giving my point of view for discussion, not because I'm disagreeing in an angry manner or out of an intent to insult - this sort of thing often gets lost over internet conversations.

I actually think a white shirt, sleeves rolled up, slim jeans, and something like Celine Jacnos or engineer boots would look good. I think we may be discussing different jeans, however - I don't mean Levis, but something more like Hedi Slimane.

If we're talking about classic style, then black shoes are already necessary because suits will be worn more often. If we're talking about modern men's "patterns" in dressing (if they can be called that), then it depends on the circles you run in/what you want to express through your style. I don't actually care if two dozen actors and upstarts wore certain combinations in the past, because they didn't invent them, and things change. The boring suit is dead, and they should now be free to to be worn how they were originally intended: with some flair!

Besides, I'm cuter than those fellows. Hard to beat individuality and presence, eh?