Top 5 Tips For Dressing Casually

Just the other day we posted some pictures to Facebook of Mike in a “Casual Friday” outfit. For those who missed it in all its loud, obnoxious glory, here’s a refresher:

Professional Man In Custom Sport Coat in Philadelphia

This got us thinking about how confusing casual dressing can be. The vast majority of the clothes that we make and talk about on this blog are dress clothes, mainly suits and shirts. This is fine, but relatively easy if you think about it. It’s a uniform, essentially: you could fill your closet with nothing but grey suits, navy suits, white shirts and blue shirts and never have to think about getting dressed again. It’d be boring, but it’s possible.

Casual wear, on the other hand, isn’t so easy because the rules aren’t so clearly defined. When are khakis and a polo shirt appropriate? How about jeans and a t-shirt? Here are our top five tips for dressing casually:


  1. Casual does not mean sloppy. Men and women alike make this mistake all too often. We’re not saying that you have to get decked out to go to brunch, but showing up in ripped jeans or velour sweatpants with “Juicy” written on the rear end signals to the world that you don’t respect yourself enough to care about your appearance. The world will return that sentiment in kind, so at least make the effort to put on clothes that fit and are in good repair.
  2. Business casual has many interpretations, so learn what’s best for your office instead of trying to wrap your head around the concept as a whole. For some industries, business casual means khakis and a polo shirt. For others, it means an odd jacket and trousers with a shirt and tie. Always overdress a little at first if you’re unsure.
  3. Be bolder with pattern and color if your personality and coloring warrant doing so. You might not be able to get away with it during your Monday morning conference call with the CFO, but a pink shirt with a blue/green plaid on top of it will look awesome with the right pair of jeans on Saturday night.
  4. NEWS FLASH: SPORT JACKETS AND BLAZERS ARE CASUAL. Relative to a suit, they are a step down on the formality ladder, so make sure you have a couple in the rotation. Solid navy, grey herringbone, and a gun check are great places to start a sport coat collection.
  5. Fit is still king. We don’t care of you paid $10 bazillion on a handmade suit made with cloth spun by magic elves; if it doesn’t fit you impeccably, you won’t look good. This concept applies all the way down to an outfit consisting of shorts, a polo, and flip-flops.

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