If you’re looking for a stellar weekend fit for an upcoming event, date night or casual weekend hang…then you my friend are in luck. It still feels like summer but it’s officially the beginning of Fall 🍁, so yeah…we’re technically in between seasons. And that might make you a little indecisive on what to wear, but I’ve got some tricks I’d like to slide your way.
1. Set a Foundation
The first tip is to set a foundational item. One item that you absolutely love to wear, but haven’t quite had the chance to enjoy in a while. It could be a cozy long sleeve Henley, boots you found at a steal, or maybe even a lightweight jacket. For me, it’s a clean pair of solid mid-top sneakers. There’s something about high ankle footwear that looks much more stylish than your typical low top. I love athletic mid top sneakers, but for today’s style session, I’m rocking with these minimal white mid sneakers. The simplicity is going to create a lot of range to work with…and by that I mean, I’m not stuck with choosing between dressy or casual clothing items.
2. Commit to a Primary Theme
Ok Great. So I’ve decided on a foundation item. But where do I go with the rest of the fit? It depends. Weather, time, and place dictate the outfit (in that order) and I’ve decided to take my wife to an outdoor theatre, then a cocktail bar for a night cap. The clock is ticking and the baby sitter ain’t free, so we’ve gotta make it snappy! 😭 Haha. And since I’m working with all white sneakers, I know ‘for sure’ that all black will be a safe bet. So for the remainder of the fit, the theme is monochromatic. Similarly, you could opt for a different theme, like vintage with a pair of flared trousers or retro colors (browns, mustard burgundy), or a sporty theme playing with colors from your alma mater or favorite sports team. It’s NFL kickoff and I know Cowboy fans out there can’t resist the temptation. LOL!
3. The Building Blocks
Whenever I’m dressing for the weekend, I like to infuse an intersectional cross between formal and casual for one simple reason. This allows me to venture wherever the night takes me, without feeling underdressed. And if I had to choose, I’d much rather be slightly overdressed than fall short of the dress code. Because truth is, I never wanna underwhelm bro! Haha.. But on a more serious note, I’m rolling with a set of black dress trousers to dress up the minimal sneakers even further.
With this pairing, it really doesn’t matter if I went with a solid colored tee, camp collar or polo shirt. It’s guaranteed to look good. One thing to note here is: pant fitment. With a mid-top shoe of any kind, it’s best to have a slightly wider pant leg opening, so that the break of the pant leg is legit. In other words, you don’t want your slim cut trouser bunching up over your high to mid-top sneaker OR boots. This can get pretty hairy and scientific …so I’ll save that write up for another day.
4. Complimentary Choices
Based on the way this fit has been built thus far, it’s hard to screw up a shirt choice. As long as it’s 1.) Black to align with the primary monochromatic theme. And 2.) Has either a tailored or relaxed flattering fitment. Because the weather is cooling down, I couldn’t pass up a chance to put this tipped knit polo to work. The next major hack, is to play around with a tucked in approach. I don’t want to disrespect this endeavor by labeling it a trend, but it’s honestly a mind blowing gesture that can significantly elevate any ‘casual outfit’ instantly! Especially when wearing trousers. So give it a try on your next outing.
5. The Final Touches
Remember what I said about ‘in between seasons’. Summer is fleeting and cool weather is approaching. So I know I won’t get much of a chance to rock this black straw fedora for the rest of the year. But it’s also super lightweight for these warm but breezy evenings, and it’s gonna take the fit up a notch without a doubt. I’ve added my typical stainless wrist watch, cuff bracelet, and silver rings…and it’s literally game over. Haha! Sorry Gents, but a fit like this will literally have you feeling yourself. At least for a bit…🙃 So I can’t wait for you to try it and put these tips to use.
Thanks again for tuning in, and until next time fellas…
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