Pros
Many of the people are like extended family. The Comer Center - free on-site gym is a nice benefit. Onsite clinic also very nice to have. How enjoyable it is to work at Lands' End can depend on what department you join, what group of people. Some are welcoming and supportive; some are less so. (Probably true anywhere.) Company is willing to promote people into new/different positions when there is a fit or near-fit, allowing career growth. Benefits are decent, health insurance, dental insurance, vision insurance, 401K partial match, various misc discounts.
Cons
No bonuses to speak of for several years. There are no cost of living raises for salaried folks, but "merit" raises, which are therefore not evenly distributed and don't always keep up with cost of living. Promotions and corresponding raises more often go to those who live in the Madison area as they are more likely to leave for a shorter drive or better paying position. Those who live nearby or are long-term employees seem to be taken for granted by upper management. Tuition assistance was discontinued several years ago.