This is part two of a three part series called Back to Basics. (You can find part one here.) I wanted to cover some typical questions I get on a regular basis.

Part two is about making better choices when dressing casually.

Two and a half men - casual?

At home, fine. Leaving the house? no.

Let’s say you have a day off, and you’re orchestrating an outfit. You’re not dressing for the office, but you also don’t want to sit around in your three-piece flannel pajama set all day. Maybe you’re heading to Starbucks for coffee with a friend, or to the park to take your corgi named Merlin for a walk. Perhaps you’re running errands at The Container Store after stopping by Whole Foods.

Here are some alternatives to the usual outfits (jeans and tee / sweatsuit / pajama bottoms with Uggs / workout gear) that people find acceptable being seen wearing in public these days.

Back to Basics: Clothe Yourself Casually

Effortless Gent: Clothe Yourself Casually

(Not big enough? Download the full image – right click and Save As…)

Let’s do a complete rundown of this graphic, starting with shirts.


The usual: A quirky tongue-in-cheek tee

The alternatives: gingham button down, polo shirt, long sleeve waffle crewneck shirt

  1. Red gingham button down by Epaulet
  2. Custom fit polo by Polo Ralph Lauren
  3. Waffle crewneck by Gap

Keep in mind: Quirky tees scream college (or San Francisco tech startup), so graduate your style and choose from one of these alternatives instead. A slim-fitting polo shirt is closest to a tee in look and feel, so if you’re big on tees, try a polo as your first small step. The button down and waffle crewneck are some long sleeve alternatives.

In general, the layer closest to your body should be your thinnest, relative to the rest of your outfit. That will keep everything in balance and prevent the universe from imploding.


The usual: Shapeless, baggy, long, light-wash jeans (I hope to God these aren’t your usual.)

The alternatives: steel gray corduroy, deep-hued twill, dark slim denim

  1. 511 gray corduroy by Levis
  2. D1 slim wine-colored chinos by Dockers
  3. 511 unwashed denim by Levis

Keep in mind: Fit makes all the difference with your garments, but especially pants. Slim doesn’t mean skinny, it means fitted to your body, not hanging off your hips. It means minimal break, not 5″ of leftover material bunching at your ankle. Also, Don’t be afraid of color. Blue denim gets boring; switch it up and try a bit of color.


The usual: Basic crewneck

The alternatives: merino or cashmere cardigan, shawl collar sweater, rugby shirt

  1. cardigan by Polo Ralph Lauren
  2. shawl collar sweater by Gap
  3. rugby shirt by Rugby Ralph Lauren

Keep in mind: Nothing wrong with a basic crewneck, but the whole point of this post and this site in general is to present you with alternatives to the usual choices so you can discover other items that make you look good.

Cardigans aren’t just for gramps anymore. Many brands make slim cut cardigans and you’ll want to stick with these modern versions to get the right fit.

Rugby shirts are my favorite alternative to sweaters, and don’t be afraid to wear a button down collar underneath. Double collars can add a nice layering effect you won’t get with just a t-shirt.


The usual: Clunky, ratty, workout sneakers

The alternatives: unadorned, simple sneakers, driving shoes, desert boots

  1. Low profile Chuck Taylors by Converse
  2. Driving shoes by Aldo
  3. Desert boots by Clarks

Keep in mind: Don’t wear Asics with your outfit. That’s something most dads wear with their dad jeans, which I don’t get. Leave the high tech workout shoes in the gym locker, and wear shoes appropriate to the situation.

Sneakers are fine if they’re something like these Chucks: Basic, low tech, simple, logo free. I prefer driving shoes in the summer (sockless? yep) or desert boots. Just make sure to check the weather (or waterproof your suede) before walking out of the house with the desert boots on.

Your turn to try it!

If you’re unsure, snap a photo or two of your outfit and send it to [email protected]. Crop your head out if you’re shy. It’d be cool to post these images in a future follow-up post. That way we can have a more in-depth discussion of what works and what doesn’t.

Check back soon for part three of Back to Basics. Remember, part one is right here.

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