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.

If this was at all useful, how about you follow me on Twitter? You could also Like EG on Facebook. Till next time.

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35 Responses

  1. Anonymous on

    Nice post, but I’m not terribly sure about the double-collaring look you suggest – seems like a thing you’d see in LessEffort!

    • Barron on

      are you saying you doubt me!? how dare you.

      actually that may not be for everyone, but i do like pulling one over a shirt/tie (loosened) every now and then. the layering really does look great. i’ll have to find a photo somewhere.

      if it’s not your thing, just disregard that piece of advice 🙂

  2. Dan on

    Big fan of the graphics like this. I bookmarked this picture in addition to your brown-or-black shoe visual guide.

  3. KCruz on

    do you have an example of the double-collaring look? i am curious as to how it would appear. any ideas would be swell as a follow-up post.

    • Barron on

      i should have an image but i’ll have to dig. did a quick google search, and it would look something like this (with a tie — and this isn’t me, if it’s not obvious)

      Michael Bastian does this often as well: I really like the look of layers and it might take a while to figure out how to pull it off if you haven’t tried it, so just play around with it a bit.

  4. Andy T on

    I love the guide Barron. I wonder how many of your ideas transfer internationally. I’m on the hunt for some Desert Boots over here in Oz as I love the idea of wearing them with my Gap jeans.

    Double layered olo shortsd were arounf back in the 80’s when I was living in England and they just remind me of back then, and not in a good way.

    • Barron on

      Hi Andy. I’m glad you like it and find it useful. I’d like to think my suggestions are applicable worldwide 🙂 Mostly because I’m all about classic looks with a modern twist, or the individual’s own taste incorporated into a standard look.

      Are you able to order from or Not sure of their shipping limitations, but I know they have a large selection of desert boots. Good luck in your search!

      • Andy T on

        Unfortunately neither ship to Australia. Having said that I have been stung buying desert boots online before. I ended up getting two pairs online as I couldn’t find any when I was off on safari. Neither pair would fit. After that I would much rather try them on. Off on a hunt for some tomorrow!

        • Barron on

          That’s a bummer. I can relate though. One pair of Clarks desert boots I have is a 9. A year later, mistakenly bought a 10 forgetting I had to adjust my size, and for some reason they fit exactly the same! No idea what’s up with the inconsistency there.

          Hope you had good luck.

    • Barron on

      Personally, I like mine to fit like a sweater would. Loose enough to where I can wear a shirt underneath, but not too billowy. Check to make sure the shoulder seam hits your shoulder bone and not your upper arm; that would mean it’s too big.

  5. Dave M on

    Found your blog recently and I’m lovin’ it. As a 43 year old dude in the tech field (travel a lot), my wardrobe needs some serious fixing. Sadly, you’ll still find me more often than I care to admit in black dockers (yes, with front pleats), a too-big-for-me polo with company logo, black socks and black basic casual leather shoes (like slip-on Dockers or similar).  I know, I know… Ugh!  

    My 2012 resolution is to really clean up, spruce up, and simplify my wardrobe. I’m getting rid of all the pleats for sure and my huge collection of t-shirts. 🙂 I also want to ditch all the company-logo’d Polos. I’m not required to wear one anyway, and the company I work for is well known enough that I’m really getting sick of the, “OH, you work for ?? I have a question about….” encounters! 🙁

    For some reason, I struggle with socks and shoes. I understand the issue with ratty athletic shoes or Asics with “dad jeans”, but how do you feel about sneakers such as Nike Free’s or some of the other minimalist/bare-foot style sneakers (New Balance Minimus comes to mind)?

    Socks always trip me up too… I basically wear black dress socks or white athletic socks, depending on the shoe. Sorry! Sometimes I wear very thin black footies with my Nike Free’s.  Have you written any articles about choosing the right socks and figuring out which ones to wear with which shoes/outfit? That’s what I REALLY need! 

    Thanks. Merry Christmas and Happy New Year! 

    • Barron on

      Hey Dave,

      Glad to hear you’re gonna clean up / simplify your wardrobe and style this year. Definitely a good idea to ditch the pleated Dockers and company-branded polo shirts. They’re not paying you to advertise, so why provide them with free promotion? 🙂

      Re: shoes, if they’re athletic, wear them for their intended purposes (ie Nike Free / New Balances for working out, being active). I’d stick to more casual, neutral sneakers for your casual outfits (think Converse, Superga, Jack Purcell, Adidas Samba).

      Re: socks, athletic socks (white/black cotton) with athletic/casual shoes. Dress socks (you need more color in your life here) with dressier shoes (leather lace ups, brogues, etc.) That’s your basic rule.

      Hope that helps!

      • Dave M on

        Thanks for the response! Regarding the socks issue, it seems the general “rule” is that sock color should match the pants. Do you agree with that? It just seems weird to wear tan/khaki socks with tan/khaki Dockers or chinos.  I usually just go with black dress socks no matter what color slacks I’m wearing. 

        Have said that, I’ve also been wondering if I should just ditch the light colored pants and stick with darker colors such as black, charcoal grey, brown, etc. I’m pretty short (5′ 7″) so it might be a better idea to wear darker colors on bottom, and lighter on top.  

        I dunno… This is going to take some time!  LOL

        • Barron on

          The reason that rule exists is because matching the color of your socks to your trousers elongates the leg, whereas a mismatching color breaks the visual line.

          That still makes sense to me, but I love color, and socks are one of the only things guys can really go crazy with, so I never really “match” anything. If you’re feeling open and a little brave, check out Happy Socks, my favorite maker lately.

          Re: pants, yes, darker colors will always look better, but you should mostly be concerned with fit. Go for a straight leg or a slightly slimmer leg. Never relaxed, those will be too baggy and make you look shorter (and fatter).

          You’ve got it, keep it up.

  6. Nicklaus on

    Just stumbled upon the site tonight and being that I like to dress with slightly more sophistication than my other 22 year old counterparts, I’ve been reading through most of what you have. 

    I do have one question though.

    What is EGs take on shorts? Is any of it ok? Khakis? Plaid? Cargo? What about fitting? Thanks!

  7. sss on

    I’ve been searching for a little while, and wondering, is there any way you could provide a link to the shawl collar sweater? I really enjoy the design of it, and the patches as well. 

    • Barron on

      Hey there,

      This article was written over a year ago, and that sweater was from Gap. Gap has a quick turnaround with its products, so that’s probably been out of stores for, 11 months now, unfortunately.

      There are a bunch of great shawl collar sweaters out there though. If there are any left, they’d be on sale (since stores now have their spring / summer collections in).