I'm often asked if there is one shoe they could buy that could be worn with jeans on the weekend, casual Friday's, a suit, and in bad weather. The answer is "NO", that magic shoe does not exist. Fellas, it's ok to have more that one pair of shoes for lots of reasons. The more you have, the longer they last. At the very least you should have 5 pair of shoes (I have more golf shoes than this!), which doesn't include your gym/running shoes, golf shoes, hiking shoes, winter boots, etc.
I'm a shoe guy so coming up with 5 was difficult for me so part 2 of this will include some additional options. Keep in mind the first 5 options can be interchanged based on color or style preference. Here we go from left to right:
1. The Chelsea Boot - This is a great addition to every closet. It's a slip on dress boot that you can wear with everything from jeans to a suit. They are easy to get on an off for those who travel, and you can find waterproof options that allow you to get to the office and about town in rain or snow while still looking your best.
2. The Dress Oxford - I suggest having a black and a brown version but, if you only buy one I will let you decide the color. This is your slacks and suit shoe for work or events. Keep them polished!!! There are lots of options for styling from the plain oxford shown to a cap toe, apron, split toe, and wing tip.
3. The Casual Oxford - Stop wearing your running shoes on the weekend with your jeans! Step up your style with something like this Cole Haan Lunar Grand Wing tip. It has the feel of a running shoe but much more stylish. There are a ton of cool options in men's footwear these days so there is no excuse for not finding something great. Don't be afraid to get out your box and pick up something with a colored sole or laces. If your job is casual you can also wear these to work.
4. The Loafer - A loafer is another versatile shoe for your collection. It can be worn to work and on the weekend. You may be scared of the Kiltie Tassel so you can get a venetian (plain upper), penny, bit, or regular tassel. The loafer is also your friend when you travel or you never learned how to tie your shoes.
5. The Vintage Running Shoe - If you are going to wear a sneaker on the weekend it should be cool. Leave your half marathon shoe in closet.
Bottom line you need more than 1 or 2 pairs of shoes and your significant other, girlfriend, or wife will appreciate it!