My friends say I dress nicely. Here's what I wear:

Volcom, Men's Frickin Modern Fit Stretch Chino Pant, Charcoal Heather. They look dressy. They are 40% synthetic so sweat/rain dries quickly. They're a bit stretchy which is comfortable. I own 4 pairs and have washed each one about 75 times. The color has faded a bit, but evenly. There is little visible wear. TCO ~$0.75 per wear. Wear with a simple brown leather belt.

https://www.amazon.com/Volcom-Frickin-Modern-Stretch-Chino/d...

Banana Republic Factory, Standard Fit Non-Iron Shirt, Sky Blue. This is a standard Banana Republic shirt, but made with more durable cloth. I own 4 of them and have washed each one about 75 times. They all still look great. TCO is <$0.50/wear. Check with 2 fashionable friends before going with a non-sky-blue color. I usually wear a thick dark gray merino long-sleeved "base layer" undershirt or a thin cream-colored merino undershirt.

https://bananarepublicfactory.gapfactory.com/browse/product....

Uniqlo, Extra Fine Merino Crew Neck Long-sleeve Sweater, Dark Gray. I own 4 of these sweaters, purchased over 2.5-1 year ago. I can't tell which ones are newer or older because they all look great. They are warm, soft, extremely durable, dry quickly, and don't hold any body odors. I wear each one about 10 times between washes. I wash them in a front-loading washer on delicate warm cycle with standard fragrance-free detergent and hang on a normal hangar to dry. TCO is <$0.25/wear.

https://www.uniqlo.com/us/en/men-extra-fine-merino-crew-neck...

Uniqlo, Cashmere Crew Neck Long-sleeve Sweater, Dark Grey. Compared to the merino one, this sweater is also durable, twice as warm, twice as soft, three times the price, and a bit shorter in the waist. Uniqlo's product is special in the industry. It's a $200 sweater for $100. $100 cashmere sweaters from other companies will pill after 5 wears and look terrible. Uniqlo's is durable. I've worn mine about 30 times, washed it twice, and it still looks new.

https://www.uniqlo.com/us/en/men-cashmere-crew-neck-long-sle...

Patagonia, Men's Torrentshell 3L Jacket, Andes Blue. This is good for wind and light rain. It rolls up into about 1L of volume. I've worn it nearly every day for 3 years, walking about 1 hour a day and riding in carshare. The waist tension cord channel fabric has worn through in the back. The jacket still looks fine and functions well. TCO ~$0.20/wear.

https://www.patagonia.com/product/mens-torrentshell-3l-rain-...

Crazy Cool, Men's Seamless Boxer Briefs Underwear, Camouflage. Underwear can be fashionable. These have no interior seams to rub against male equipment. If you have a belly crease, the wasteband will start to roll after 5 wears, but it's not too tight. They can smell if you sweat repeatedly. They dry quickly. The legs ride up. I expect final TCO to be ~$0.20/wear or lower.

https://www.walmart.com/ip/Crazy-Cool-Men-s-Camouflage-Seaml...

Woolly Clothing, Merino Wool Long Drop Boxer Brief, Everyday Weight, Charcoal. Extremely expensive and extremely comfortable. Wearing these and using a bidet will solve all body odor issues below the belt. The "long drop" version doesn't ride up your legs. The company had fabric durability problems but solved them. These wear out by getting holes on the seat after about 50 wears. If you have a belly crease, the waistband will get a crease after 15 wears and can roll and become tight and uncomfortable. TCO ~$0.55/wear.

https://www.amazon.com/Woolly-Clothing-Merino-Boxer-Brief/dp...

Columbia, Men's Newton Ridge Plus Ii Waterproof Hiking Boot Shoe, Cordovan/Squash. These are roomy in the toes and flat inside (no "arch support"). The interior fabric and tread wear out after about 750 miles of walking. TCO ~$0.10/mile. If they wear out within a year, ship them to Columbia and they send you a $96 gift card.

https://www.amazon.com/Columbia-Newton-Waterproof-Hiking-Cor...

Nike, Men's Revolution 4 Running Shoe, Black/White/Anthracite. These are flat inside (no "arch support"). I put these in the washer every 6 months to whiten them up. To wash, remove the laces and inserts, put the shoes and everything into a mesh bag, and wash them on a delicate warm cycle. The tread lasts a long time. The inserts and interior fabric fail around 750 miles. TCO ~$0.10/mile.

https://www.amazon.com/NIKE-Revolution-Running-White-Anthrac...

Darn Tough, Vermont Men's Merino Wool Boot Full Cushion Sock (Style 1405), Charcoal. These are the best warm socks. I wear them all day every day, even at home. I walk 1,000 miles a year and go through about 6 pairs a year. TCO ~$0.13/mile. Darn Tough makes many variations of socks so be sure to get the full cushion version.

https://www.amazon.com/gp/product/B01ENQYZIE

O'Neill, Loaded 2.0 Hybrid Shorts, Heather Black. Comfortable and quick-drying. With a collared shirt tucked in and a belt, you'll look "loaded".

https://www.amazon.com/ONeill-Loaded-Hybrid-Shorts-Heather/d...

Minus33, Merino Wool 703 Algonquin Men's Lightweight Short Sleeve Crew, Dark Gray Heather. Super-quick drying, nearly eliminating body odor. Extremely durable fabric and stitching. They keep their shape. They don't fade. I own four, purchased 4-6 years ago. I have probably worn the oldest one 100 times. I cannot tell which one is the oldest. They all look fine. TCO ~$0.50/wear.

https://www.amazon.com/gp/product/B000R7E1LU

Tortuga, Outbreaker Daypack. Chest strap. Understated logo. Comfortable even when full and heavy (2L drinks, 13" Macbook Pro, charger, headphones, sweater, jacket, lunch, snacks, & workout clothes. Water-resistant zipper stops being water resistant after about 1,000 zip/unzip cycles. Stitching around top handle fails after about 1,000 miles. TCO ~$0.10/mile.

https://www.tortugabackpacks.com/products/outbreaker-travel-...

----

I wash my clothes in a front-loading washer on a delicate warm cycle and dry on delicate warm. I take them out immediately after the dry cycle finishes and hang them up. I never iron. All wool skips the dryer, going straight from washer to a hanger or clothes-pin rack.

https://www.mamaslaundrytalk.com/the-proper-way-to-hang-dres...

For drying socks and underwear on the bathroom door:

https://www.amazon.com/Whitmor-Clip-Drip-Hanger-Hanging/dp/B...

https://www.amazon.com/Over-Fitting-Sized-Doors-Unjumbly/dp/...

For drying sweaters and shirts:

https://www.amazon.com/JEFEE-Garment-Clothes-Storage-Fashion...

If you use a top-loading washer with an "agitator", double or triple the TCO numbers. Such washers destroy clothes.