Applying "Shoe Rules" to Boots

Sometimes I am annoyed when I read these on-line “style guides” whose authors have made some statements that are derogatory about wearing boots in particular situations, such as in a business settings. Oh well, their loss; some of them just don’t get it.

Anyway, I found a silly “25 Shoe Rules” on the about.com website, and thought I would offer a Bootman’s perspective. Below, the “shoe rule” is in regular type. My suggested “Bootman’s Rules” are in italics below each “shoe rule”. Enjoy!

1. Your shoes should be darker than your pants.
Your boots should be darker than your pants if wearing dress pants. Otherwise, boots that contrast with jeans look great!

2. Your shoes should be the most expensive part of your wardrobe.
Your boots should be the most expensive part of your wardrobe.

3. No socks with sandals.
Men should not wear sandals. Period. Nobody wants to see your feet. Nobody.

4. Buy new flip-flops each summer.
Never buy or wear flip-flops for any reason. They are unsanitary, unsightly, and just plain wrong on so many levels for adult men.

5. Be careful when wearing sneakers with khakis, you run the risk of looking older than you are.
Wear boots with khakis for an interesting appearance of style and fashion.

6. Your socks should be a nice bridge between your shoes and your pants.
When you wear boots, no one will see your socks. But always wear comfortable socks that are part wool, part cotton, and part synthetic, to have the advantages that these materials offer (absorption of sweat, comfort, and durability).

7. Your dress shoes should always be shined and looking good.
Your dress boots should always be shined and looking good.

8. The darker your suit, the darker your shoes.
The darker your suit, the darker your boots.

9. No flip-flops at work. Unless you work at a surf shop.
No flip-flops, period. See revised rule #4.

10. Match your socks to your shoes.
This is repetitive. See revised rule #6.

11. Know how to shine your shoes, and if you can’t do it, find a professional shoe shiner. You’ll get great looking shoes and an interesting conversation.
Know how to shine your boots, and if you can’t do it, find a professional shoe shiner. It will probably cost a bit more to have boots professionally shined, but you WILL have a great conversation (as those guys rarely have the chance to shine men’s boots).

12. Always spend money on shoes rather than shirts or pants.
Always spend money on boots rather than shoes, shirts, or pants.

13. Loafers go with just about anything.
Repeat after me: loafers are what you find sitting on the couch. Boots are what you find on your feet.

14. When in doubt, go conservative over edgy.
When in doubt (about wearing boots), go conservative, but stop obsessing about what other people think. Wear boots!

15. Always choose fit over style.
For boots, always choose fit over style, even if that means having boots made custom to your size requirements.

16. Cowboy boots don’t work with suits. Unless you are a real, honest to God cowboy.
This is bullshit stereotyping. Cowboy boots DO work well with a suit, regardless of your employment. Get over the self-imposed fear and learn that dress cowboy boots go quite well with suits! (proof here).

17. Be fitted for running shoes if you’re going to push yourself.
Be fitted for tactical boots if you’re going to push yourself.

18. Wingtips are cool again.
Wingtip boots are cool again.

19. Make sure you have one great pair of boots.
Make sure you have at least two great pairs of boots so you can let your boots breathe between wearings. As you obtain more pairs of boots, you can donate your shoes to charity.

20. Your shoes should match your belt.
Your dress boots should match your belt.

21. Replace your workout shoes at least every six months.
Replace your tactical workout boots at least once a year (boots last longer than sneakers.)

22. Don’t wear sandals if you have gross feet.
Don’t wear sandals at all. See revised rule #3.

23. Buy a nice pair of brown oxfords, they go with almost anything.
Buy a nice pair of brown dress cowboy boots to alternate wearing with your black dress cowboy boots. They go with almost anything.

24. Splurge once a year on that pair of shoes you really want.
Splurge once a year on that pair of boots you really want.

25. Try out the new athletic shoe trends before training with them.
Just cut to the chase, and buy tactical boots to wear if you will be engaging in sports or running.

So, there you have it — a Bootman’s take on silly “style rules for shoes.”

Life is short: wear boots! Dump the shoes and never, ever, wear sandals or flip-flops.