It’s the special date night, pivotal interview morning, long-awaited sales presentation day, evening out with colleagues, or weekend with the family. The clothes you’ve selected compliment the confidence and poise you have, but what shoes will complete the look best for the specific occasion? Men’s shoe options can be so vast, so how do you know which pair is right for you? Let’s open up your shoe portfolio and make the best choice…
The Shoe Portfolio…
- The Oxford: (Refined, Timeless, and Dressy) – Formal Events
- The Classic Boot: (Casual, Classic, and Authoritative) – Business Casual Environments and Outings
- The White Sneaker: (Versatile, Simple, and Clean) – Casual Settings and Weekend Wear
- The Double Monk: (Fashion-forward, Suave, and Distinguished) – Business Professional and Casual Events
- The Loafer: (Dynamic, Relaxed, and Dapper) – Casual, Formal, and Weekend Wear Settings
1. The Oxford 
2. The Classic Boot 
3. The White Sneaker 
4. The Double Monk 
5. The Loafer
Dressing well is a form of good manners.
Tom ford – Fashion Designer
1. The Oxford
“Refined, Timeless, and Dressy”
The Oxford is the most refined men’s dress shoe. Generally worn in darker shades of brown and black, they’ll pair exquisitely with your suits or tuxedo. The timeless classic is marked by the closed lacing system and emphasizes your professional and sophisticated demeanor.
Where to Wear: Formal Events
- Business professional events and meetings
- High-end date nights
- Formal concerts and shows
- Black-tie events
- White-tie events (if shined high-gloss black)
*Tip: To dress-down for a less formal outing try a wingtip-oxford.
2. The Classic Boot
“Casual, Classic, and Authoritative”
The Classic Boot is the go-to for keeping your style classy in all casual settings. Crafted in leather and suede, boots are worn today in three primary stylings: the Chelsea, Cap-Toe, and Chukka – all of which look terrific with jeans or khaki pants. When wearing, make sure to never tuck in your pants, but lace-up and go command stylistic respect from those around you.
Where to Wear: Business Casual Environments and Outings
- Business casual events and meetings
- Nights out: concerts, date nights, casual social gatherings
- After-work: coffee-shops, breweries, and out-on-the-town
- Day-to-day activities
*Tip: On a cold or rainy day, try a boot with no toe-guard and throw on a business casual suit.
3. The White Sneaker
“Versatile, Simple, and Clean”
The White Sneaker is your ultimate weekend shoe. Constructed from leather or canvas, the simple selection keeps you comfortable yet fashion forward. As a result, they are perfect for the every day activity: the sneakers can be worn with your jeans, khakis, trousers, or even your favorite shorts.
Where to Wear: Casual Settings and Weekend Wear
- The day off of work or relaxing weekend
- Sporting events, concerts, and other related festivities
- Day-to-day activities
- A casual date
*Tip: Throw on these shoes, a simple t-shirt, and a bomber or workwear jacket and enjoy a leisure filled weekend.
4. The Double-Monk
“Fashion-forward, Suave, and Distinguished”
The Double-Monk is an iconic leather men’s shoe that reflects your elevated self-expression while maintaining the classic look respected in your professional circles. It can be dressed up or down and is well-suited for a variety of activities. In all settings, the fashion-forward selection sets you distinctly apart from your colleagues as a style-conscious and adventurous individual.
Where to Wear: Business Professional and Casual Events
- Business professional settings
- Networking events
- High-end outings and date nights
- Office wear
*Tip: Strap on a pair of brown double-monks with a two-piece blue or grey suit and distinguish yourself from the rest of the office.
5. The Loafer
“Dynamic, Relaxed, and Dapper”
The Loafer is the slip-on, dapper throwback from the 50’s. Fastened from leather or suede and ranging in style from Penny to Snaffle, the loafer is the recognizable pair that exemplifies your relaxed yet get-things-done personality. Loafers are your highly versatile option and can be worn well with your summer shorts or dressed-up with an ankle-length trouser suit and no-show socks for an advanced casual look.
Where to Wear: Casual, Formal, and Weekend Wear Settings
- Day-to-day activities and an adventurous weekend
- High-end and casual date nights
- All concerts and shows
- Some white-tie events and award show environments
*Tip: While stylish and worn well in most settings, avoid wear in the workplace or business professional settings.
Now that you’ve chosen your perfect pair, you’re ready to hit the streets in style for any occasion! If you’re still looking for just the right fit, go visit our friends at Paul Evans NY to complete your shoe portfolio or secure any of the pictured selections above.
Our Partner
Special thanks to our friends at Paul Evans NY for letting us display their shoes in this post. To learn more about Paul Evans NY visit their website or check out their Instagram.
