Okay, today I am really looking for critical input. A few times, the AI app goes a little wonky in putting together a lot of colors. Most of the time I blindly try it, more sartorially knowledgeable gentlemen here have noted it works. Today... let's find out! Things I know: my jacket sleeves bunched up before I got into camera position. I am actually looking into arm bands as a short-term solution and welcome feedback from anyone who has used them. I also changed the pocket square and cufflinks to get a red theme across the upper portion of the outfit, aligning with the vest. Finally, I know this is very autumnal. The AI app is clearly pushing me to write code that will override using outfit themes that are aligned with a season long since over. I used to think I didn't care but now I think this just shows a lack of diversity in options, which is not accurate (my outfit combinations are just under 2 sextillion... I think I can craft a few of those to be non-autumnal!). I welcome all of the feedback here, as always. I have included the AI app's rational for the colors at the end of the outfit details. • Odd Jacket — DOJ‑004 (Botany): A classic tan worsted wool odd jacket with notched lapels and dual rear vents. The neutral tan creates a warm, approachable foundation that works beautifully with the windowpane vest—perfect for internal leadership discussions without the formality of a matched suit. • Slacks — SL‑021 (Ralph Lauren): Mid-gray wool slacks with a subtle basket weave/shadow stripe texture. Classic fit with excellent drape—the gray provides sophisticated contrast against the tan jacket while anchoring the outfit's warm earth-tone palette. • Shirt — DS‑044 (Charles Tyrwhitt): A white non-iron poplin French cuff dress shirt with semi-spread collar (5" spread). Cotton construction with high opacity and crisp structure—the French cuffs elevate the look and demand attention-worthy cufflinks. • Undershirt — US‑014 (True Classic): A gray cotton-polyester blend crew neck undershirt. Provides invisible comfort under the opaque white poplin without any show-through risk.

I’m in my early 40’s and have gotten to a point where I don’t like a lot of stuff in my pockets. I don’t like the look of bulky pockets and my wallet leaves a mark on them wearing out a spot. I also started needing more stuff when I’m out and about so I have a very cheap sling bag off amazon at the moment and looking for something new. What do you guys think about a man wearing a sling or messenger bag? Does it look dumb and if not which one do you prefer and why?