As we just discussed, a complete wardrobe has boot styles for all types of occasions.

If you’re only going to invest in one boot for the season, however, I would recommend a lace-up wingtip brogue, like these badass chocolate brown “Daltons” by Allen Edmonds.

The trim leather sole, sharp toe and rich color make them appear dressy while the tall lace box, full broguing and toe medallion make them appropriate for casual wear as well.

Here, I spent five days in these guys to break them in a little.

Monday 

If you’re wearing boots with a tailored look they need to look sharp (and polished) and the suit should be cut from a Fall/Winter weight fabric – think flannel, corduroy, tweed, moleskin, cashmere, etc.

With a suit, keep the boots laced tightly all the way to the top. This keeps them looking nice and clean and allows your trousers to fall over them naturally.

A wide 2″ cuff looks great on trim-cut trousers in heavier fabric and gives the hem a little weight, pulling the pant down and allowing it to drape properly. And no, you don’t need pleats to have a cuff – don’t be restricted by these old fashioned “rules”.

Bonus Tip: The shirt, tie and suit all have a flannel finish, which makes this outfit very soft, warm and comfortable.

Bonus Tip II: The more-versatile-than-you-think flannel double breasted suit again, as featured here.

Bonus Tip III: A single-breasted coat over a double-breasted suit is more visually appealing than the other way around. A DB coat just covers up all the layers of your outfit.