Timex Weekender - my daily watch for nearly 15 years.
Classic, timeless, and easy to maintain. Not much else to ask for, especially since you can switch the band when bored.
Incredible jeans.
The barrel shape is interesting without being hard to wear, the denim is sturdy but not overly hefty, and the belt is great once you get used to it.
Had to adjust to sizing - the XL fit perfectly despite being a M in most other brands.
Alden full strap calf loafers - "full strap" and "calf" tend to get hate from menswear enthusiasts but given the price of leisure handsewn these are a great alternative.
Try on in store if at all possible.
