Oxfords: The Classic Choice

Oxfords are timeless. Seriously, they're the epitome of sophistication. Think sleek black leather oxfords for a formal event, or try a bolder color like burgundy for a touch of personality. I own a pair of Allen Edmonds Park Avenues—they're a splurge, but worth every penny. They've seen me through countless weddings, job interviews, and even a rather epic dance-off (don't ask!).

• Pro Tip: Look for oxfords with quality leather and good arch support. Your feet will thank you later, I promise!

Loafers: Effortless Chic

Loafers are perfect for that 'dressed up but not too dressed up' vibe. Gucci loafers are iconic, of course, but there are tons of great more affordable options available if you want something equally stylish without breaking the bank. I personally like to pair mine with well-cut chinos or dark jeans for a smart casual look. They add a touch of sophistication without seeming overly formal.

Chelsea Boots: The Edgy Touch

Chelsea boots offer a bit of an edge to your footwear game. They're versatile enough for both casual and semi-formal occasions. The elastic side panels make them easy to slip on and off, which is a major plus when you're rushing out the door. I've noticed a lot of people styling chelsea boots with slim-fit jeans or suits for a smart style look that is not too formal or casual.

• Style Tip: Try a pair in suede for a richer texture, but be prepared for some extra care (suede cleaner is your new best friend!).

Monk Straps: A Touch of Sophistication

Monk straps bring a unique, sophisticated flair. They're like oxfords’ more refined cousin. The buckle detail adds a touch of personality, and they're surprisingly comfortable for extended wear. I've worn mine to art gallery openings and business dinners, and they always seem to make a statement.

• Consider this: Monk straps come in single or double buckle styles—choose the one that best suits your taste.

Boots: The Fall and Winter Staple

When the weather turns cooler, you can't beat a good pair of dress boots. Think about leather chukka boots for a rugged yet refined look, or go for something more formal like leather riding boots. I generally prefer chukka boots for their versatility. They can be dressed up or down, making them a great investment for your wardrobe. Also, I’ve seen a lot of people wearing them with jeans for a more casual yet stylish look.

Wingtips: The Bold Statement

Wingtip shoes are definitely a statement piece. The distinctive brogue detailing makes them perfect for those who want to stand out from the crowd. However, it is best to avoid wingtips at too formal events. While I love a good wingtip, it is best to keep them to events where you want to make a stylish impression, but it is not too formal.

• Important Note: They can be a bit more challenging to style, so make sure the rest of your outfit complements the boldness of the shoes.

Derbies: Comfort and Style Combined

Derbies offer a happy medium between oxfords and loafers, striking a balance between formality and comfort. They're super versatile, working equally well with suits or more casual outfits. Plus, the open lacing makes them easier to adjust for a perfect fit. I find Derbies super versatile for both formal and casual occasions, making them a worthwhile addition to your wardrobe.

Espadrilles: Summer Style

For warmer weather, espadrilles are a stylish and comfortable option for casual events. They're lightweight and breathable, perfect for long days exploring a new city or relaxing on vacation. I’ve always been a fan of espadrilles—especially during summer. Try to wear them with shorts, chinos, or even some linen pants for a comfortable and stylish look.

Slip-Ons: Easy and Stylish

Slip-on shoes are all about convenience. They're great for everyday wear, and surprisingly, many stylish options are available. Look for ones made with quality materials like leather or suede for a more sophisticated look. They are a great casual wear item and I find them really versatile for my style.

Brogues: The Classic with a Twist

Brogues are similar to oxfords but add perforated detailing, giving them a bit of texture and personality. They’re a great choice for adding a touch of character to a more formal look. I would recommend pairing brogues with chinos and a button-down shirt. Try to experiment with different colors and textures.

Boots (again!): The Versatile Choice

I mentioned boots earlier, but they deserve another mention because of their versatility. From rugged chukka boots to sleek Chelsea boots, the options are endless. Think about investing in a quality pair in neutral colors like black or brown; they’ll go with practically everything! Remember, when picking a pair of boots, make sure the material and design match the formality of your occasion.