Theodore 1922 is a high-end men's clothing store in the Annex. In between all the used book stores it's a little out of place but I love going there.
They are very helpful and clearly know and care about clothing and fashion. The clothing is expensive and you are obviously paying more for the expertise, dedicated service and to support a small business. The clothing ranges from conservative (navy blue suits) to very fashion-forward (exotic patterned shirts). Prices are much more reasonable during the sales, usually twice a year.
There is obviously a bit of sales pressure but its not overwhelming and the experience is always positive.