Q. What kind of shoes work best with fall and winter clothes? I have a somewhat conservative business office, and like go to high end restaurants on weekends. Are my white rubber-soled dark leather shoes okay in the coming seasons?

A. I’m glad you asked, and, while I don’t want to be harsh, I would say they are not appropriate in those settings at any time of year. In the first place, I would not even call those shoes, I consider them to be sneakers.  I have trouble accepting the popular look for even slightly dressy occasion. Sneakers certainly do not fit any but the most informal office; also, if you feel the rest of your outfit should be dressed up in a restaurant, think the same of your footwear.

Adjusting clothes for both the season and the event is important, and I am a great believer that shoes often define the man. As long as they are not gimmicky, most men’s shoes are fine with the clothes that take us into fall. Depending on the occasion and what else you’re wearing, some dress shoes are more suitable than others. In the well-dressed world (where sandals and sneakers just don’t cut it), two types of shoes are acceptable, lace-ups and slip-ons.

Both are crafted of smooth, supple leathers, and both are best when they are simple, straightforward, and free of unnecessary decorative touches – assuring that they will always look appropriate no matter the season or the occasion.

Leather lace-up style shoes that well-dressed men wear are black, dark brown, and sometimes cordovan. Only those colors are appropriate for business and dressy wear. Even though other colors, such as navy, gray, and tan, are perfect for suits and blazers, they are not acceptable for dress shoes. There are essentially three varieties of lace-up oxfords:         

• Wing-tips – you can wear them all year round, but be sure that their level of formality is appropriate with the other items you are wearing (that is, that they are not too formal).
• Cap-toes – this less dressy style is versatile enough to work with suits that are light and casual or dark and dressy. They’re also perfect with blazers and sport coats, or with chinos.  
• Plain-toes – are great shoes to own. In rich, dark brown, they are ideal with more relaxed tan and khaki suits; yet in black they are even more dressy than the other two styles, and, in a pinch, can double as formal black-tie footwear

Every man should also have a few different pairs of slip-on shoes: 

• Classic loafers.  Only in the stuffiest of traditional circles are these considered inappropriate for business. They also go with every form of casual dressing.
• Boat/deck shoes.   These casual slip-ons offer a lot broader range of colors. For example, they can be worn in navy, gray, even bright red.
• Saddle Oxfords. One of the best-dressed guys I know likes to wear eye-catching two-color pairs with his casual, weekend wear.

At the barest minimum, I recommend investing in a pair of fine cap-toe lace-ups in either dark brown or black and two types of slip-ons. Keep in mind that simplicity is the key to good taste in all things, and nowhere more so than in shoes. 

A final useful note: It is a smart move to buy a pair of dress shoes before you need to wear them. Even if you don’t wear them often, when it’s time to wear them, you’ll be glad you have them. A suit and sneakers (even that contradiction of terms, “dressy sneakers”) just won’t cut it for a a job interview, an important meeting, or a wedding. Rushing to find a pair of dress shoes before an event limits your options, and wearing brand new shoes that have not been “broken in” could be so uncomfortable that you don’t enjoy the occasion. Shop ahead of time.

Please send your men’s dress and grooming questions and comments to MALE CALL: Lois.Fenton@prodigy.net