Julie Rath: To Tuck or Not to Tuck — Wearing Boots

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.