“You have good taste, but you dress very casual.”
My dad assesses an entire situation in a succinct declarative statement. In context, he was telling me about a very sharply-dressed guy my age he saw at a meeting, wearing a seersucker suit.

Selfie at the Oxford Exchange: Gant Rugger dreamy “Hugger” oxford I had additionally tailored (darts in lower back)
As usual, he’s right. Pretty much since age ten, I have relished in the perfect basic item, and likewise spurned the many I’ve owned over the years that have been far from perfection.
I can fixate on jeans that fit like a second skin, though finding them isn’t as easy as you’d think. The same goes for v-neck t-shirts. Hoodies, etc. Color, cut, fabric feel, and overall quality after a couple of washes are all potential pitfalls on the path to near-perfection.
Give me a pair of venetian loafers, dark tapered jeans, and a variety of tops and coats. I will add sparkle and glam with neat hair, subtle jewelry, and a bag, wallet, or shoes that have been chosen with careful consideration.
When I look at the universe of menswear bloggers, instagram accounts, and general idea of what mens’ style is, all I see is blazers and suits. Sportcoats and office separates as far as the eye can see.
Sure, in Manhattan or London, I’d have to invest more heavily in biz-casual, and dilute it down to ‘going-out wear’ or an ‘after-hours uniform,’ and rely on a handful of weekend standbys. But elsewhere in the first world, the opposite process prevails.
Silicon Valley, arguably the source of future world trends related to technology and business investment, is more James Perse than Hugo Boss.
With proper attention to the details, not unlike traditional suit tailoring, you can dress up a fine jeans-based outfit easily, with an unstructured sport coat or untucked dress shirt.
How I see it, why would I get excited about something that piles on the layers (especially in this climate!), is usually an imperfect cut, if not custom tailored, which can cost into the thousands. Even if not that dear, such pieces still cost a ton on a per-wear basis.

These Peal & Co. for Brooks Brothers monk strap shoes I’ve had for five years are about the dressiest it gets
Plus, I have to find the right shoes, the right socks. And it’s not like you can wear the same suit five days a week.
My immediate reaction to wearing a tie is to remove it. Unless it’s loose, I CAN’T BREATHE!
Once I got in trouble for not wearing socks to a civic group presentation. A board member was front and center, and she reported back to my boss on my bare ankle display. The nerve.
I’ve been thinking about this a lot, the dressy/casual dichotomy. I just want to look good. No rules, no “must have jacket and slacks.”
How about I wear jeans that are better-tailored, a dry-cleaned gingham shirt made in Italy, and suede loafers that probably cost more than your clunky Aldo shoes?
ICK!
This realization and assertion of nonconformity means I can’t get enough of those ingredients with which to build a veritable casual re-per-toire. I.e. jeans, shorts, slip-ons, sandals. Tees, polos. I just belong in Cruise season year-round.
See Style Staples on Pinterest.
Some key items in my closet: Jil Sander plain or color-blocked tees, Vince hooded long-sleeve double-layer tee, Nudie Jeans Grim Tim fit in 11 year wash, Gant Rugger gray cotton hoodie with navy satin lining, Barena wool vest, and a number of plain James Perse round and v-neck t-shirts.
Ask me about suiting, and I will consult outside expertise. Ask me about casual wear, or accessories, or shoes. And we’ll chat.