Because I, like many others, particularly like shoes, and because shoes are - barring suits - generally the most expensive investment one is likely to make in a wardrobe certainly at least when building a wardrobe, I have sought to make a thread dedicated to seeking out the five best shoes types to make for the person constructing their wardrobe. Now, because I have said that these shoes are for the person building their wardrobe and this wardrobe is supposed to be a versatile one, it is important to get Aristotelian and define, or at least shed some light on, what I think is versatile and for what wardrobe type this is to be. Given that I personally see myself going into a field for which the dress code is more relaxed (business casual or lower) that will be the starting point for this discussion. However, given that I also want a versatile wardrobe, I feel like this wardrobe should have the ability to combine elements to become at one moment business formal (CBD) and at the same time be able to be worn in a strictly casual sense (though I likely myself wouldn't go much less formal than business casual due to personal preference). This means that there can't be any one item that fills a niche role so specifically it can't really be also worn in other circumstances. For example, if you wanted to get as formal as possible and get some white tie/black tie appropriate pumps, those wouldn't really be able to be worn with much else in a congruous manner in my mind. These type of shoes for specific (usually niche) purposes just aren't too versatile. So the shoes must be able to be worn in a majority of settings (casual, smart casual, business casual, CDB). Furthermore, it seems important to consider the climate in which one lives in order to properly construct any wardrobe, and certainly to discuss the footwear for said wardrobe. I'll confine my climate to one that gets your traditional four seasons - though not necessarily the extreme harshness of one season over others. To give some sort of definitive reference just assume a climate like that of the Middle Atlantic region of the US up to the Northeaster region of the US. There is a summer, which can sometimes be muggy and hot; there is a winter, which can sometimes get extremely cold and snowy/wet; and there are most any conceivable middle grounds in between. You may have noticed that I haven't mentioned another important concern when discussing building a wardrobe: budget. This is mainly because I only want to discuss type of shoes, restricted to style and color (e.g. a brown suede chukka, a black cap-toe oxford), rather than recommending a specific shoe. The decision of how much a person wants to spend on their particular shoes is personal, and I'll only give provisions for what type of shoe I think should be bought. Finally, as an aside, I quite like boots, and as such I haven't limited my "shoes" to be only shoes and without boots. I'm a fan of shoes in general and I would love for this to spur discussion both in relation to my needs or goals outlined here, and for others to construct versatile shoes for different wardrobe types (e.g. a lawyer usually only found wearing CBD). So if in the discussion we want to try and make a wardrobe of only shoes or only boots, I'd be happy to join in and help. As of right now, there can be shoes and boots in this wardrobe. So, in summary, the versatile wardrobe I'm building for will have to accomplish: Run the gamut between CBD and strictly casual (though average/predominantly business casual) Fit a climate with extremes at either end, typical of the mid-Atlantic up to Northeastern US Be versatile enough to combine with most elements in the wardrobe (i.e. no opera pumps to fill that black-tie niche) In no particular order here is what I would think would give me a versatile wardrobe: 1. Black cap-toe oxford I feel like this shoe is necessary as it allows me to get up to CBD, and is really the only shoe I'll include that can do that for me. It is still casual enough that it can be paired with most anything else - even jeans, though it probably is a little out of context in strictly casual (jeans and a t-shirt) settings. I also feel like it can be formal enough for a black-tie setting, though I'm aware that technically in black-tie one is supposed to have a sleeker shoe, so the captoe is a crutch in that regard. 2. Dark brown suede chukka This seems to me to be a staple of any versatile wardrobe. It looks excellent with jeans, chinos, cords, and sometimes works with pleated and creased trousers (though as I type it I'm not very sold on that). Regardless, it works in many settings, and in a wardrobe such as mine which is predominantly business casual, it'll be worn quite a bit. Make sure to get a rubber-soled one and treat with waterproof to be able to wear them on rainy days. 3. Tan plain-toe bluchers These are again a very versatile shoe. The blucher in general is more casual than an oxford, and the tan color is casual and versatile as well. I can see these being worn with anything a chukka can be worn with, and they seem to be better able to work with pleated and creased business trousers and graphite/navy suits. The nice tan color looks great in summer in my opinion, but that doesn't mean they can't be worn year round. 4. Suede penny loafers These seem like a great go-to summer shoe. They can be worn without socks (though maybe if only unlined?), with shorts if so desired, and with jeans as well. Definitely not formal enough to be paired with a suit, but they'll do great in most casual wear. I'm not really sure what color would be best, but if they're more a summer shoe then maybe it would be better to go with a tan or a light colored one. 5. Dark brown wingtip boot This may just be my preference showing through. But I feel like these work great with any type of casual look; they can look good with jeans, chinos, cords, and trousers. These would probably have to be waterproofed and have a rubber sole to deal with winter mixtures and fulfill that role of my wardrobe, and if that's the case then I'm not too sure if they would be not sleek enough to be paired with a suit. But there you have it. Let me know how I did, what you would change in my lineup, and any misconceptions I seem to have about dress, dress codes, and versatility in general. I hope this will start some discussion on five shoes to buy for different kinds of wardrobes in addition to discussions on how well or poorly I did in accomplishing my goal.