Dressing a Middle-Aged Man
A lot of older men tuck their shirts in all the time, and I think this is a big mistake. The older you get, the more you sag, so tucking will only accentuate that. It's okay to do so when you have to, such as a dressier situation, but for corporate casual or anything less, just let it hang out. The other piece of clothing that ages men is those navy blue blazers with the three brass buttons on each sleeve. Just like women, men are getting lots of choices of blazers, so pick a nice one and use it to dress up jeans or cords, like in the outfit at left. Fabrics that flatter include tweeds and corduroy - suit materials should be left for the suit. The earth tones help to keep the outfit from looking too young, but the collared sweater with zipper make this otherwise avuncular look more modern. Footwear is also an important choice to make, and if you happen to own shoes with tassles on them, get rid of them immediately! Yuppie-wear is strictly prohibited in the 21st century, so instead go for a casual oxford with a squared toe. You'll look appropriate but also hip.
Let's say you're going on a date, and corporate casual makes it seem like you just wore your work clothes out. The two wardrobes should be different! In most cases, as you age, stick with the classics - pieces that stand the test of time - with a modern touch. A black blazer with a button down, like in the outfit at right, is youthful but flattering, and the khakis make sure the outfit isn't too casual for a nicer restaurant. The scarf is up to you, but I think it goes overboard. That's where I think youthful takes a wrong turn into midlife crisis, so I'd recommend just the tried-and-true outfit underneath. Of course, the thing you must keep in mind at all times is how comfortable you feel in an outfit. If you think you look like a fool in an outfit, you most likely will - confidence is what you'll need to really pull any outfit off. I know, it sounds like girl advice, but it's guy advice, too. Remember - you're at the age where you've moved beyond having something to prove into living well as the best revenge.
Let's say you're hosting game day at your house and you want an outfit to chill with the guys in. Jeans are an indispensable staple, but I recommend you go with classic fits and washes rather than some of the trendier sorts. I also suggest darker washes to flatter the figure more. The outfit at left is a great choice, and also illustrates the excellent technique of layering. Pairing an earthtone with a brighter color, like in this case, is a great way to experiment with bolder looks. Again, the sweaters are also more modern than your typical sweatshirt. The word on the street is individualism, so embrace it wholeheartedly and pick all kinds of different things. Now, the real beauty of the three outfits is that they didn't come from expensive department stores - they all came from Old Navy. That's right, folks, everything was inexpensive, but at least you'll get a pretty decent quality for your money. Hope that helped, Mike!