Staring into the void of your closet annoyed you don’t know what to wear can be the worst part about an evening engagement – especially if it’s a low key but sophisticated destination.
It’s not uncommon for a guy to have his work style dialed in – he has to wear it most days, after all. Professional, put-together, respectable to the older higher ups without feeling like a complete doofus to his peers or that one mega cool client that comes in town for meetings every so often.
But the confidence starts breaking down in those stray off hour evening engagements. Those invites that definitely call for casual but not like “just wear whatever” casual, the faux casual that slyly proclaims, “I’m so well dressed normally that even my casual is put-together.”
“Ugh,” I hear you saying, “I have no interest in that.”
But I’m going to push back and say that’s probably just frustration and annoyance at always staring blankly into your closet 45 minutes before you’re supposed to be somewhere on a random Friday evening, feeling like you’ve got no clue what to wear, and hating that you even have to put this much thought into it.
Well I hear you. I’ve literally run a men’s website for 14 years that has helped millions of men clarify, simplify, and upgrade their personal style and I still regularly have the same experience.
That’s why I’ve put together this casual outfit inspo that will come in handy anytime you’ve got somewhere to go in the evening that is casual but needs to still be refined.
Not only that, I’ve included a few variations where a simple swap can edit the outfit to be more appropriate for different scenarios.
A Casual Evening Outfit Inspo
The first place I start with any evening outfit, regardless of dress level, is with color. Since the black tie dress code is society’s uniform for formality, literally western culture’s definition of dressing intentionally, we can make two logical deductions. First, in the strictest sense, adding bright colors to clothing reduces their formality, and second, wearing dark clothing “seems” more intentional.
So as we back way down the formality ladder to something more casual, we’re going to stick with a darker outfit to be dressed casually but appear more formal. What comes after the equals sign in that equation is a casual outfit that is comfortable, absolutely does not feel out of place next to a guy in a t-shirt or a blazer.
Bomber Jacket: Levi’s
Sweater Polo with Johnny Collar: Nordstrom
Charcoal Jeans: Proof / Budget alt: Amazon Essentials
Watch: Tissot
Socks: Nordstrom
Sneakers: Nike
Cologne: Tom Ford Ombre Leather
The Bomber Jacket
The bomber jacket, also known as the flight jacket, is one of the most popular casual jacket types. Originally created as a functional jacket for the US military after World War 2, it has now become a fashion staple. The bomber jacket was first adopted by British subcultures as a tough alternative to the collared Harrington jacket in the late 1960s. Over time, it has been embraced by male icons like Steve McQueen and has been sent down the runway by famous designers like Louis Vuitton, Yves Saint Laurent, Dior Homme, Givenchy, and Zegna. The MA-1, a nylon jacket first issued to US Air Force and Navy pilots in the 1950s, replaced its predecessor, the B-15. Today, the bomber jacket is available in a variety of colors and thicknesses and can be found in stores like Target, Amazon, Urban Outfitters and Nordstrom.
The bomber jacket is incredibly versatile when it comes to style, as it can be worn with different levels of dress, especially for casual and smart casual looks. Look for less puffy bomber jackets for maximum versatility; it makes it the type of jacket you don’t have to remove when you go inside. You can wear a bomber jacket with jeans, chinos, or dress trousers. It also pairs well with a simple t-shirt (see below), sweater, or button up shirt.
The Sweater Polo
Nordstrom / Budget: Saks Fifth Avenue / Alt: Abercombie
The sweater polo, as the name suggests, is a combination of a sweater and a polo shirt. Unlike a standard pique polo shirt, the sweater polo is made from knitted fabric and is softer, warmer, and more comfortable. Also known as a knit polo, it’s perfect for smart casual outfits, especially during colder months. Depending on perspective, it’s either a dressy polo or a nice sweater with a collar, either way you can dress it up or down, depending on the occasion.
This type of collar specifically is known as a Johnny collar. It features a short, unfolded collar with a round, open front (button-less) neckline. This style of collar is typically less formal than a traditional button-up shirt collar on a dress shirt but still offers a polished look.
You can wear it with jeans, chinos, or trousers, and it also pairs well with a jacket or a blazer, heck it’s even a great, comfortable choice with joggers for a put-together but cozy at-home look:
For more tips on how to style a sweater polo, check out why the knit polo will change the way you dress. Also, check out four tricks for wearing polos if they make you feel like a dork.
A More Casual Swap Out: Bomber Jacket with a T-shirt
T-shirt: Lucky
The sweater polo is a fantastic choice for dressing up or down, but maybe it’s a smidge dressy for where you’re heading. You can easily edit this evening outfit by swapping it out for a tasteful t-shirt to go another notch down on the casual spectrum.
A More Colorful Swap Out: Vibrant Knit Polo
If you want to inject some color, either to be less formal or to be a little more playful, you can swap the sweater polo for something Dwayne Johnson would definitely rock. Unfortunately, more budget-friendly retailers haven’t caught up to the trend, so this one isn’t cheap but it is by one of the best men’s clothing brands.
Charcoal Jeans
Proof / Budget alt: Amazon Essentials
Charcoal jeans are a great alternative to regular blue jeans. They’re just as universal, but have a more sophisticated look. The dark gray color is less harsh than jet black, making them easier to pair with different styles. The Rover Pant at Huckberry is a great option, it’s crafted with 73% cotton, 25% Sorbtek, and 2% lycra, providing durability and stretch.
Watch
If you’re in the market for a refined timepiece that won’t break the bank, look no further than the Tissot PRS 516 Powermatic. With a 42 mm case size and a sleek 316L stainless steel construction with ceramic bezel, this watch is sure to turn heads by watch nerds and laypeople alike. As a Swiss brand with over 150 years of experience in watchmaking, Tissot has a reputation for producing high-quality timepieces at affordable prices. The automatic Powermatic 80 feature gives it an impressive 80-hour power reserve.
Socks
It’s easy to assume that if you’re wearing sneakers then you would wear casual socks like athletic socks, but I prefer to wear crew socks more akin to dress socks. It makes the outfit feel cohesive with the rest of the intentional pieces and this is especially important if you end up as a guest at a shoes-off home.
High Top Sneakers
The Nike Blazer Mid ’77 is an iconic high-top sneaker that has been a staple in sneaker culture since its release in 1973. With a sleek and simple design, the Nike Blazer ’77 has been a favorite of sneakerheads for decades. It features a suede toe cap accent, and a large vintage Swoosh. The Blazer ’77 has been updated over the years with new materials, colors, and patterns, but overall remains a classic.
These are the closest thing to high top Killshots you’ll find, and in black tow that line of sneaker and boot. The leather makes it just a tad bit dressier than what you’d get with a pair of high top Converse (which would also be a good swap if you’re looking to switch things up).
A Dressier or More Rugged Swap: Chunky Chelsea Boots
If high tops just aren’t your thing or you’re looking to augment the outfit slightly more formal or slightly more rugged, a chunky pair of Chelsea boots is a sharp style that is secretly mega comfortable. I’ve been wearing them for years.
Cologne
When it comes to men’s style, fragrance is an essential component that can easily be overlooked. Cologne is a subtle yet powerful tool that can enhance your personal style and leave a lasting impact on those you interact with. One fragrance that has been making waves in recent years is Tom Ford’s Ombré Leather Parfum.
This fragrance is perfect for those who prefer scents that are woody and smoky. The middle notes of jasmine sambac and orris add a floral touch, while the base notes of leather, woody notes, and tobacco give a warm and masculine aroma that lasts throughout the day.
If you’re looking for a cologne that exudes confidence and sophistication, Tom Ford’s Ombré Leather Parfum might be worth considering.
A Dressier Edit
This makes for such a solid base, that we can continue swapping out items to make a full business casual edit of this outfit:
Sportcoat: Todd Snyder / Dress Pants: Spier & Mackay / Suede Loafers: Winthrop Hamilton (also worn here)
Like this look? Chat with me in the comments!
