Q & Answer: Suggestions For Stylish Boots?

Samson writes:

I am currently on the hunt for some stylish boots that could work for both casual and semi-formal occasions. I’ve looked at various Red Wing (white soles- questionable for more formal occasions), Clarks (nice, but I already own a pair and would like to try something different), Frye (kinda butch), etc… but none really do it for me.

I happened upon these by Alden that I really like (even my fiancé loves them)  but they are both sold out and not anywhere in my size… oh and quite expensive (but if everything I’ve read about Alden is true then maybe worth it). Anyway I’d appreciate any suggestions.

It will be difficult to find boots that are both appropriate for casual wear and for semi-formal occaisions.  Boots are generally out of place with any but the most casual suit, casually worn, and most boots aren’t appropriate even with a sportcoat.  That said, you do have options.

You can go with a casual boot.  The Red Wing Gentleman Traveler is a great option here, especially in black cherry.  This boot will smarten up jeans or cotton pants, but you wouldn’t pair it with anything more formal than that.

You could also consider a Chelsea boot.  R.M. Williams is an Australian manufacturer who make whole-cut (meaning the only seam is at the back), elastic-sided boots that in their sleeker (and low-heeled) versions can look equally at home with blue jeans and wool pants.  I’d consider the flat-heeled, chisel-toed models, like the Craftsman pictured above.  Williams have a store in NY, or can be ordered online from Australia – shipping runs about $30, and the boots are a bargain at about $250.

If you’re looking for a dressier boot, you could try one from one of the mid-end traditional English manufacturers, like Tricker’s or Grenson.  Above is the Grenson Sharp, a brogued boot with a larger, more traditional toebox that could certainly be worn with jeans or your favorite country clothes.  I grabbed these shots from the excellent Pediwear.co.uk.  You can also find seconds of some of these mid-level English brands for less on Ebay.

You’re right to consider Aldens, as well.  Alden is America’s finest traditional shoe manufacturer, and they offer a variety of great styles.  There are several retailers that specialize in Aldens, and they have a store in San Francisco.  Leather Soul of Hawaii has a number of lovely exclusive Alden boots.  I’ve included a plaintoe called the Flextoe, version of their iconic “Indy” boot in super-durable shell cordovan and left out some other beautiful shoes.  If I were going to recommend one shoe for this purpose though, it might be the last Alden, a simple chukka.  At $400 or so, it’s no bargain, but with good care it will last you the rest of your life.