The outdoor apparel industry is the standard bearer of endless technical revolutions, and in the last few years, has become fashionable as well. All my clothing is hiking clothing. It is extraordinary performance apparel, and looks really cool.
1) Shirts. Do not buy cotton. It offers no insulation value, soaks up sweat, and stays wet all day long. Get polyester or merino wool. Both wick sweat and dry quickly, thereby keeping you cooler in the summer, and warmer in winter, and you can wash them in the sink. I am a big fan of Patagonia's Capilene line, which offers excellent performance, and also contains an anti-odor treatment (polyester usually soaks up body odor), and the lightest weight version looks like an ordinary t-shirt.
If you're not familiar with merino wool, it is a super-comfortable natural fabric that provides similar performance abilities, but feels even less clammy than polyester. It is also itch, shrink, and odor-free. You can wear it for a week and no one will know. However, it is also twice as expensive at $50 a t-shirt. It also dries a bit slower than polyester, making sink-washing a bit slower (it can also over-stretch when soaked; wring it out gently and lay flat to dry). This can be mitigated by buying the lightest weight fabrics. Brands include Icebreaker, Smartwool, Ibex and Patagonia. All use the same material, so just pick what fits and looks cool.
I prefer ultra-light t-shirts rather than heavy pieces. They work in summer to cool off, but still work as winter base layers. If you buy warm base layers, you can only wear them in winter, and you'll have to carry t-shirts anyway. Secondly, they dry faster, making sink-washing easier. I prefer to leave the insulation to the other layers, which you won't need to wash as often. Lastly, buy stuff that looks cool. There should be no difference between daytime performance and evening coolness. If you feel awkward wearing it, you will end up not wearing it.
2) Underwear. The same rules apply here. Let me tell you, having performance underwear feels just as good as it sounds. Spoil yourself.
In winter, you should probably get at least one pair of long underwear. It will prevent the heat loss from your legs and keep your entire body warmer. I like to wear regular underwear underneath them, so I don't have to wash the long underwear as frequently. I went with green, so I can look like Robin Hood.
Tip: if you go clubbing in them, you will feel as if your legs are on fire. If you plan on going out, leave them and deal with being cold on the walk to the club.
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