What to wear with black military style boots

Published on April 15, 2013

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Q: “Enjoyed your How to Dress Down Your Suit Jacket story. Do you have any tips for wearing what a vest casually?” – Patrick N. 

A: Often we get asked about how to wear a vest with a suit and we’ve written a whole article about how to wear a vest with a suit the modern way but we’ve also got some tips on wearing a vest casually. So go ahead and give that suit jacket or blazer a day off and give that vest a little moonlighting as a stand-alone piece. In fact, a vest can be a perfect candidate for achieving that dressy-but-not-too-serious-and-still-looking-better-than-99%-of-the-room look at the next after work social.

Here are a couple of our favorite ways to wear a vest for that casual, weekend warrior look:

How to wear a vest casually: Give the vest the spotlight.
  1. Give the Suit Jacket a Rest – Leave the jacket at home and wear that vest with a well-fitting button-down shirt and some suit pants. For an even more relaxed look, opt for a more casual button down like an oxford or a chambray. And if you’re knotting up, reach for something a little laid back like a knit or cotton tie, rather than a more formal silk tie. Feel free to keep your shirt collar unbuttoned with a loosened up tie knot to let people know you’ve switched from work mode to play mode.
  2. Go Vest + Jeans – If you’re pairing your vest with some jeans, you want to go for a dark wash with no fancy fades, major whiskering, holes or bagginess. Make sure the denim is a slimmer fit, so it’s consistent with your vest. With the right pair of jeans, you can achieve a smart casual look and avoid a jarring juxtaposition between dressy and casual. You never want to look business on top and over-relaxed on the bottom.

And please don’t attempt to pull off some 3-piece hybrid like this, which will make you look like you lost your pants and had to borrow some jeans from your dad.

As for the vest itself, make sure it fits snug, with the length long enough that the sides reach to your belt line. And remember to leave that last vest button unbuttoned.

So give your vest a chance to shine. It’s a great way to add some versatility to your outfit. Mix and match, get creative and see what you can come up with!

Got any questions or outfit suggestions on wearing a vest casually? Leave a comment below! 

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