Casually Tailored: A Simple Style Solution

What’s the best way to throw something on that looks put together but doesn’t go overboard? One of the simplest solutions is to combine casual and tailored elements. I like to call it sharp casual, but you might also consider it being “casually tailored.” Here’s one way to do it that will work any day of the week.

Brown Suede Boots - He Spoke Style

| WEARING | J.Crew blazer, Michael Andrews Bespoke waistcoat, Brooks Brothers Black Fleece shirt, Jeans c/o Armani Exchange, Oliver Peoples sunglasses, Drakes pocket square, Timex watch, To Boot New York suede boots | PHOTOGRAPHY | by Rob McIver Photo

A waistcoat instantly dresses up a pair of slim denim and adds depth to a look, not to mention an extra layer of insulation, which is important during the winter/spring transition. Get the most out of a winter-weight fabric like tweed by finding ways to appropriate separates seasonally.

The formality (or lack thereof) of any outfit is defined in large part by the type of collar on your shirt. Banded collar notwithstanding, a button-down collar is the most casual option and a great choice when wearing tailored elements without a tie.

Brown Suede Boots - He Spoke Style

Suede is often seen as a fall fabric, but as I talked about in one of our very first style posts, don’t discount it as an option for spring. A nice pair of suede boots should be in every well-dressed man’s shoe repertoire.

Brown Suede Boots - He Spoke Style

Thanks for reading.

Stylishly Yours,

He Spoke Style

Chime In

  • Eoin Brennan

    Its a great and look and I’ll definitely rob that one, just a question about the pocket square though: Do you not think it makes the look too formal and thereby taking away from the Casually tailored appearance?

    • Brian Sacawa

      Thanks for the comment, Eoin. Tom offers a great answer above. A pocket square is the finishing touch that pulls everything together, whether you’re talking about a formal look or something more casual like this one. Cheers!

      • Eoin Brennan

        Cool thanks Brian

  • Tom B


    You need the pocket square, trust Brian! Like the Big Lebowski’s rug, it’s what “pulls the room together.”

    Notice that Brian is wearing a nice casual puff (silk?) with a flowing pattern print on it (paisley?) in browns echoing his shoes and the waist coat. It’s a casual highlight, doing exactly what the pocket square is supposed to do. If he were wearing a white linen or formally patterned square in a fold instead of a puff (think Mad Men), then it would indeed be too formal. Look at northern italian men’s fashion – Brian has a lot of links here on his site – they pull if off perfectly. Sprezzatura……

    Now if you REALLY want to pull off casual elegance, check out lsat year’s April 1 post:

    The outfit is obviously missing a pocket square, but I was hoping to see Brian outdo himself this year…



    • Brian Sacawa

      Ah, so sorry to disappoint on the April Fool’s post this year, Tom! I’ve been running on fumes while traveling the past month — finally heading home tomorrow — so we were unable to pull something together.

      Regarding the pocket square, it’s a light wool number from Drakes full of pheasants and other sporting imagery. It’s the same one I was singing the praises of in this post:

    • Eoin Brennan

      Thanks Tom, I Too am a fan of the Dude and his rug. Think I’ll throw this look together at the weekend.

  • jennifer

    How can you mix an earthy toned vest with blues?

    The top half elegance vs the bottom half casual is cool, but the elegance
    doesn’t jive. A brown jacket or definitely grey would kick. Maybe even black
    since its so versatile.

  • Mugsy Jeans

    Great point on the collar. I always struggled with pulling this look off. The problem I had is the waist-down would look too casual compared to the waist-up. The collar trick subtly resolves that.

  • Mens

    Such a nice finish. i would love to carry this look for my office and casual tours . Well the suits are important in a men life . i came to know about the importanc eof suits from .