Building Your Shoe Wardrobe

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  • Building Your Shoe Wardrobe - Oxfords, Derbys, Boots, Loafers
  • Building Your Shoe Wardrobe - Oxfords, Derbys, Boots, Loafers
  • Building Your Shoe Wardrobe - Oxfords, Derbys, Boots, Loafers
  • Building Your Shoe Wardrobe - Oxfords, Derbys, Boots, Loafers
  • Building Your Shoe Wardrobe - Oxfords, Derbys, Boots, Loafers
  • Building Your Shoe Wardrobe - Oxfords, Derbys, Boots, Loafers

Building the Right Shoe Wardrobe

Like any part of a good wardrobe, building the right shoe collection takes a lot of forethought and planning. There are hundreds of beautiful shoes out there, but not all of them are worth buying. Figuring out which ones are requires seriously thinking about what works for your lifestyle and needs. It’s perhaps for this reason why so many “essential shoes” lists ring hollow – because they assume too much about their readers. Thus, we present to you our list of “essential shoes,” but with a bit more explanation about what clothes and environments they might be best suited for, so that you can decide which are right for you.

Dress Shoes

First are your dress shoes, which include open laced oxfords (where the eyelet tabs are sewn under the front of the shoe) and derbys (where the eyelet tabs are left open, sitting on top of the shoe). Oxfords have a sleeker line, thus are considered more formal. They’re useful if you wear suits often. If you’re mostly in sport coats, then get derbys, as they carry a slightly more casual sensibility. Derbys can come in a number of forms – Norwegian split toes, wingtips, or simply plain, to name a few. Get whichever strikes your fancy, but know that the more details there are on a shoe, the more casual they’re considered (same goes for oxfords).

If you wear tailored clothes often (that is, suits and sport coats), then you’ll need at least two pairs of dress shoes. This will allow you to properly rotate through your shoes so that each pair can have a full day’s worth of rest after each wear. If you don’t rotate through your shoes, the sweat from your feet will break the leather down faster, so give them at least a full day to dry out.

Weekend Loafers

Next come your weekend shoes. For spring and summer, we suggest slip-ons. There are a dozen variations – driving mocs, horsebit loafers, boat shoes, camp mocs, monk straps, etc. A pair of horsebit loafers will have a sleek, slightly more European styling, while tassel loafers can be distinctively American. These days, you can wear slip-ons with almost anything – fuzzy woolen trousers with a light blue button up shirt, cotton chinos with a long sleeved polo, or even just jeans and a t-shirt. They are on the slightly more dressy side of casual (compared to the running sneakers most men wear today), but useful if you like to look a bit dressed up without seeming overdressed.

Weekend Boots

Similarly, for fall and winter weekends, we recommend boots. Again, there dozens of variations. Something like balmoral boots will be quite dressy, brogued boots will be rustic, and Chelsea boots a bit British Mod. There are few, however, that are more basic and versatile than your simple brown leather chukka. Pair them with jeans, moleskins, corduroys, or heavy woolen flannels. They’ll go with everything as casual as a quilted jacket or waxed cotton coat, to something dressier such as a tweed sport jacket.

Simple Canvas Sneakers

Again, both the leather slips on and laced boots will be on the smarter side of casual. For something true-blue-casual, which you can wear almost year-round, there are canvas sneakers. These can be a relatively cheap way for you to add another pair of shoes to your weekend rotation, and thus invest a bit more in your leather footwear. Plus, white canvas sneakers can look more harmonious with certain casual ensembles than leather shoes of any stripe.

Of course, only you can figure out what mix of shoe styles is right for you, but at least now you know what might be some of the reasoning. Take a look out our collection of Italian dress shoes to find the best pair that suits your style.


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We recommend ordering a full size below your regular US dress shoe size.

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Like most other Italian brands (Gucci, Prada, Tod's), our shoes run a full size larger than US dress shoe brands.

Extra room in your toes is by design. Think sleek and sexy.


Resist the urge to press down on your toes to assess the fit. There's always going to be extra room because of the shape of our shoe lasts.

You have the perfect fit when:


There is enough room across the widest part of your foot and your heel sits comfortably in the shoe. If you can confidently strut your stuff in the shoes, you're good to go.

And don't worry about minor heel slippage or extra room in the your toes!

Minor heel slippage is normal in a new pair of leather-soled shoes.


After you break in your new shoes, the heel slippage will stop. Our Italian calfskin leather needs a chance to conform to your foot. If it doesn't, email us and we'll make it right.

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