One of the first things women notice on men is their shoes. No, really. Below I take you through the main categories of boots and explain what to wear with each and address the tuck-or-not question. (Hint: it has nothing to do with whether or not you have nice ankles.) 
The Work Boot – Utilitarian and rugged in feel, but handsome nonetheless, the work boot is best worn casually. It’s often water-resistant with a warm lining and therefore great for negotiating snow drifts. And besides, if there’s any falling timber on the Upper East Side, you’ll be ready. Note: this boot looks better when it’s a little beat up.Tuck? Yep, especially when there’s a layer of slushy muck along the sidewalk. You might need to cuff your pants once or twice for this, and you can also try leaving your boots untied or loosely tied (depending on how long your laces are – you don’t want them dragging through black puddles) and pushing your pants easily into the tops. Don’t worry about making sure each pant leg looks exactly the same. It should be a little undone. 
The Chukka – Originally worn by polo players (the name is derived from the word chukker, the playing period of a polo game), the Chukka is now worn by all men, regardless of whether they carry a mallet. This low-style boot can be dressy or casual, dictated by the material it’s made from – usually suede or leather. Wear them with jeans, chinos, dress pants or a suit, depending on how refined the boot material is.Tuck? Never. 
The Lace-up Boot – These boots are your most versatile option and come in a range of heights. Pull them on with jeans and a leather jacket (make sure the shade of the jacket leather is the same as that of your boots). Or wear them with a suit for a sharp-dressy look that also keeps your ankles warm as you power across town during an arctic blast.The lace-up boot is a candidate for one of my favorite fashion moments: the nonchalant half-tuck. While you’re welcome to play it safe and wear your pants over your boots, why not show a little lace and let the bottoms of your chinos or jeans – cuffing or rolling optional – fall casually into the tops of your boots? Don’t make it too perfect. Note: if you’re feeling noncommittal (or are short on time), lace them halfway, then wrap the laces around the tops of your boots a couple of times and tie them, as in the image below.
Tuck? See above. 
The Chelsea Boot – Formerly reserved for riding your scooter around London to visit your favorite Beatle, the Chelsea boot now gets a lot of airplay in mainstream menswear. This style is often characterized by an elasticized side panel that makes it easy to pull on and off – great for zipping through airports. Wear with dark jeans for a night out or with your suit for an effortlessly sleek look.Tuck? Don’t even think about it.So that covers my general rundown on boots. For specific boot suggestions, please contact me directly. And, as always, I welcome your suggestions and comments.