Quote:
Originally Posted by DionTheDman
For a first pair, I'd suggest the regular strand not the weave. Much simpler.

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You'd get a ton of mileage just with those two.
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Strand in a lighter brown colour are a fantastic choice for business casual. My only addition to that piece of advice, is that the Strand model tends to be expensive. AE has so many styles, that you can get a model almost identical to the Strand for a lot cheaper.
The Park Avenue is currently on sale for an extra 30% off in card:
https://www.allenedmonds.com/burnish...322_color=3324
Less than $200 total.
The Strand itself is on sale for $268.44 + GST:
https://www.allenedmonds.com/shoes-b...273_color=3355
The McAllister Wing Tip is nice:
https://www.allenedmonds.com/shoes-b...03B_color=6203
Depending on how casual the office is, a relatively low cut boot is a good option:
https://www.allenedmonds.com/shoes-b...start=1&sz=226