I can hear it now: “But Andrew, actually sportcoats ARE casual jackets. Did you know they were originally made for hunters in the UK?” Yep, that's true, and it's pretty crazy to think that what was essentially the Real Tree Camo of the day is now considered appropriate for a first date. BUT, let's be real. Sportcoats in today's culture are dressy. They're used as a tool to make a statement about the occasion or venue that you're showing up for.
Having said that, I ask you this: Isn't a herringbone sportcoat really just a shorter walker coat? The material is similar, the lapels are the same. The waist suppression is the same.
So if you're a guy on a budget, don't waste a couple hundred dollars buying a sportcoat and then only wear it twice per year when you have a wedding rehearsal dinner to attend. Get some use out of it! Throw it on over a sweatshirt and pair it with dark denim. It'll keep you warm on your journey and you can take it off when you arrive, just as you would any other coat. I would add the caveat that this works specifically with a tweed-like sportcoat like the one I'm wearing. A traditional blue-and-gold-button blazer doesn't work the same.
I really like my President boots from Thursday Boots and I find myself wearing them all the time. They're sleek and minimal, skipping the bulk and chunk of other heritage boot styles, making them complementary to everything you wear it with. Dress them up with wool trousers, or rock them with jeans and a henley. You'd be hard-pressed to find a full grain leather boot, Goodyear welt construction, and glove leather lining that doesn't require a break-in under $300.
Most briefcases suffer from one of two problems: They either look like they're housing the nuclear codes or you feel silly carrying it anywhere that isn't a boardroom. Similar to the boots, this briefcase from Daniel's NYC has a design that looks appropriate in a coffeeshop or walking into a client meeting with some higher-ups.