The Difference Between Dressing Well And Dressing Up
Dressing up implies formality (weddings, professional settings, etc), and dressing better is an educated skill. While the tools of dressing better are applied to dressing up, the formality of the latter isn’t necessary to have the former.
Ponder the following when navigating the art of dressing up and dressing well.
When not sure if a look is appropriate, show up early when going to a party/event
Regardless of how good (or bad) you look, shave off some awkwardness by entering a relatively empty room. It may seem counterproductive (you won’t be able to know what everyone else looks like), but it will get you acclimated.
Chatting with the other early birds, drink in hand, you’ll avoid walking in with all eyes on you, and be relaxed once the crowd arrives.
2. Show up Very late
Alternatively, you can take the other route, and show up when the party is roaring.
You’ll walk in, take in the scene, and if you don’t match it, escape and do better another day.
(I certainly hope you won’t escape the party. Rather escape the embarrassment and learn from the experience.)
Bonus: Alcohol would have been flowing freely by then, leaving beer goggles to help with any subtle mistakes.
3. Start with what is most important
You’re way ahead of the game if your shit fits and is decent quality.
Focus on that first and foremost. At a black tie event, if you accidentally wear a light blue suit that is of excellent quality and fits well, you’ll look better than the guy who is wearing a tux that fit fifteen pounds ago.
In that situation you would have made the wrong decision in etiquette, but the right decision in dressing well.
4. Eventually OverdressinG won’t matter
Outside of key social formalities, (weddings, professional, the beach), most settings are appropriate for any degree of attire.
For instance, where I grew up (in the middle of no where Catskills), dressing well was one step above the Marlboro t-shirt you got from submitting your UPC points.
Even wearing a nice quality white t-shirt with tailored denim would be the mark of someone “dressing up”. Low barometers exist everywhere. In the grand scheme of things, the only one that matters is yours.
5. Fake it until you make it
Confidence isn’t a guarantee of a well-made choice, although it surely helps when taking risks to find the right ones.
While overdressing for an occasion is sure to attract a few side glances, don’t let it hinder you from trying. I’d rather see you looking a little over the top than not growing, expanding, and expressing.
6. don’t be Dumb
Don’t do obvious things like not showering before a date for the sake of laziness or making excuses.
Looking like a schlub doesn’t make you less of a “try hard” nor does not keep you from being noticed. It gets you noticed for unfortunate things.
7. Better to over than under
As the saying goes, it is better to be overdressed than underdressed. Hell, I am always a little more fancy than necessary. What can I say? I like a pretty dress or some elegant shoes. That doesn’t mean I look out of sorts and wear a sexy evening dress to an 11 AM brunch. It means that I take care in the details of my outfit and that effort captures attention.
