Any guy who has a fun, outdoorsy personal life and a buttoned-up office job knows how difficult this polarity can be to balance. Sure, you know you can’t wear your vintage beer tee to that charity gala, and you also know you don’t break out your Cape Cod Oxfords for a day of tossing Frisbee with Fido. But since you do have a balance to maintain, why not treat yourself to all the shoes it takes to get the job done? Business, pleasure, and all things between these stark swings of the pendulum can be matched with all kinds of shoe styles from 20, 40, 60, or even 100 years ago.

The sneakers that work for weekend jaunts

Fun in the sun or driving up the coast with your best girl and man’s best friend is all about comfort and style. The go-to for a lot of guys is skate or soccer shoes, including Vans slip-ons or a timeless classic like the Adidas Samba. But you can up the ante and improve your overall look with Nike fashion footwear or Supras, both of which will offer you cloud-like comfort in addition to their clean, sporty, haute couture look. If you have a little more scratch to spend, you can also get true couture sneakers from Gucci, Armani, and other high-end names, but keep in mind, these more expensive shoes don’t usually offer the same level of comfort as their Nike or Supra counterparts — additionally, the big names at Fashion Week followed the lead in fashion sneakers from Nike, Supra, and other skate shoe brands — not the other way around.

Meet me at the clubhouse for a martini

You definitely shouldn’t cruise to your “optional” weekend picnic with the bigwigs wearing your Chuck Taylors — especially if you’re up for that big promotion. However, you don’t want to overdress for a casual event either. Depending on what the weather is like and what kind of event you’ll be attending, there are a couple of really fun, hip options. For the more business than casual event where chinos, cardigans, or sports coats will likely be the dress code, try a twist on the fashion of the day with a two-tone Derby brogue. These lace-up dress shoes are loaded with personality, but there’s nothing Vegas about them. Think golf course without playing golf, or corporate party at a mountain chalet in spring. For summer events at the beach, riverside, or at a company summit where boating or more relaxed wear is at play, try a men’s moccasin or topsider in navy blue or brown, which both offer timeless class and comfort, and can be worn in warm or cool weather, with or without socks.

The charity dinner, corporate gala, and black tie affairs

One of the biggest mistakes some guys make is to play it tongue in cheek by suiting up a perfectly gorgeous couture suit or tuxedo and try to get a laugh by pairing it with sneakers. Do not be this guy unless you’re hosting the Nickelodeon Kid’s Choice Awards. In any other instance, pick an elegant classic. You can add a little personality with a black on black wingtip, or keep it simply sleek and perfect with a squared-toe, lace-up black oxford, or for especially formal events, a black paten leather classic cap toe slip-in.