Having a casual yet professional look is not always an easy thing to do. It’s not as simple as throwing on a pair of Jeans and a button down shirt and calling it a day. It involves careful planning and also having some confidence to pull the look off.
Start by wearing jeans that actually fit your body type. There are numerous websites that can assist you in finding the right jeans for your body type. I personally like the Levi’s jeans site and try their fit guide. And if you go into a Levi’s store there will more than likely be staff can help you find the right fit and maybe even a tailor on hand. I am only speaking from my personal experience but they are great at fittings and the jeans are not too expensive. You can also go to the larger more upscale department stores like Nordstrom or Von Maur and they can fit you as well. The main point is to find the jeans or pants that fit your body type. With jeans there is not one style that fits all. For example, I am about 5’6″ and around 135-140 lbs (yeah I know I’m small) so I would look best in a slim fit Jean. Not a skinny jean but slim fit. There is a difference.
Now on to the shirt. The button down shirt should not be too loose as it will make you look like a slob and the necktie or bowtie will not look right. If you button your shirt at the top and you can still stick your finger inside the collar and touch your neck it is too big. You can also get measured by a tailor or at a department store for the correct fit. I prefer the fitted dress shirt because it is a little tighter or form fitting than the regular fit but it is also not very forgiving so if you’ve had a few beers over the years and the gut to prove it then the slim or fitted may not be your best option. If you choose a regular fit I suggest that you try it on. This pretty much goes for all clothes really. A medium from one designer may actually be a small or large from another.
As you can tell having the correct fit is very important if you want to look any way other than a slob or bum. That look went out in the 90’s. The tailored look is in and hopefully for good.
Wearing a pair of sneakers with jeans a dress shirt and tie is okay for some occasions. I wear this combination often to work myself. Having the right pair of shoes is the key. You want something that will blend with the rest of the attire and not stick out too much. You don’t want it to look like you went to the gym before work and forgot to pack your dress shoes. You want it to look like the sneakers are a part of the outfit and something that you planned to do.
Something like this might work:
What you are looking at is a pair of black slim fit jeans, a red gingham pattern button down fitted dress shirt, a silver/gray bow tie (I can never tell the colors apart) and a pair of black/gray/red sneakers to tie everything together. This is not a hard look to pull off but it can be a bit tricky. Try to Mix and match your casual and dress wear in your closet and see what you can come up with.