We’ve talked about airport attire before. Today I was boarding my plane in my usual business airport outfit: dark denim, loafers, collared shirt, sport coat with pocket square. I also had my killer Saddleback Leather briefcase. Two flight attendants greeted me. One looks me up and down from head to toe…”You look very nice.” “Thank you,” I replied, “I appreciate it.” “No, we appreciate it,” she countered with a smile. Flight attendants, always look professional and put together. Dressing nicely in their place of work repays, in a small way, the respect and care they show us as we travel.

Decided to elevate today! Blue dress shirt under a Brooks Brothers camel lambswool sweater vest. A beautiful paisley, madder silk tie from Brooks Brothers. A tweed sports coat and brown corduroy trousers on top of some brown suede loafers. Feeling good!

For the past few months I've been homeless and living in the shelter system. Please don't ask what happened, I'm not going to go into that, nor am I looking for sympathy. I'm sharing this because one thing that doesn't get as much discussion when talking about style, but is very important when you're homeless, is the base of the style pyramid, function. The picture with the sweater and tie is how I would normally dress for work, and the other picture is clothing that has been my uniform in the shelter. In my uniform I'm wearing a long sleeve cotton t-shirt as a base layer. A navy polar fleece replaces a wool sweater as an insulating layer under my winter parka (not shown). The flat cap I got at Marshall's for $8 on sale (I have a black touque for the cold days). The pants are heavy weight cargos (one to two sizes too large), and themal underwear underneath. Finally I have a pair of the standard white cotton socks and a pair of wool socks I can double up over the cotton ones when going outside. I also have a pair of $10 aviators I got from Amazon. How these fit my functional requirements: 1. You don't stand out in the shelter, you don't want to be a target for theft or appear too much as an authority figure (a lot of the guys have problems with authority). 2. The outfit still has good color style and still looks well put together, particularly with the flat cap. This is important so you don't look homeless when out shopping, dining, or other daily life tasks. When people think you're homeless, they treat you differently. With this look, I could just be any guy who works in construction or a warehouse who didn't have time to change. 3. The clothes are durable. They can be worn 24/7 for days at a time between washing, can handle winter snow, wetness, and salt, and don't snag or rip easily. 4. Don't show dirt easily and can handle punishing laundry systems. 5. The bagginess is actually a bonus. You can layer up easily and trap warm air between layers. It also allows for more comfort while sleeping in the same clothes as you wear during the day. 6. Cargos are considered by many something to be avoided nowadays, but when you're homeless, the pockets help.

Sharing some wrist shots from a trip a few weeks ago

For the first time in about 20 years, I have cleared out my closet. It was necessary: I lost some weight and started doing CrossFit. Before I buy new things, I try out combinations of the clothes that still fit me or fit me again. My office outfit for today consists of: blue jacket white long-sleeved shirt blue scarf (to protect my neck) brown leather belt (matching my shoes) blue jeans long socks in dark navy brown leather shoes BTW: Antonio would probably say ‘those shoes scream 2000’. And yes – they are almost 20 years old and probably no longer fashionable. However, I didn't want to just throw them away, as they were expensive at the time and I have taken good care of them over the years. What do you think? Should I get rid of the shoes? Any other helpful proposals? Additional information: I bought the shoes years ago because a friend of mine said I should buy a pair of "respect shoes" sometime.