As a young child, I cared very little of fashion. I didn’t care if my hair was combed, if my jeans were dirty, or what my sweater looked like. I just didn’t want my clothes to itch. What kid can stand itchy clothes?

So Mom and Dad and Grandma and Grandpa would do their best to buy me non-itchy clothes that they felt like I looked good in. I shouldn’t say “looked good.” I should say “adorable.” They loved it when I looked adorable. Whether it was a hat that looked like a pumpkin or a miniature baseball jersey, my parents loved it when other parents would say, “Oh - doesn’t he look adorable!”

This pattern continued for many years. By the time I was a young teenager, I had an undeveloped sense of fashion and, like most boys my age, just wanted to find a way to fit in at school. So I resorted to wearing baggy jeans and sweatshirts most days. I only “dressed up” on forced occasions when I had to take my one pair of dress pants and a colored dress shirt and put it on for some holiday or special occasion. And I hated it.

An extended period of time in college, exposure to both the arts and business worlds, and some mentoring from a distinguished English gentleman has allowed me to create for you what I call Timeless Trendy. This is a system that I developed that makes my wardrobe and fashion stay in style for considerably longer than the average “trendy” individual. How often do you see people spending a small fortune on clothes every other month? Sure, they’re wearing the “in thing” now, but what they’re wearing turns into garage sale material in about six months. Here’s a run down of some things to look for that will make your fashion dollar stretch further.

Here are a list of items to be on the lookout for. I’m going to cover t-shirts and jeans in detail today, and the other items over the course of the next two or three months.

Black dress shoes
Black dress socks
Dark Suit
Dress shirts, french-cuff
Button down shirts, button-cuff
Cuff links
Tie(s)
Jeans
Black Belt
White t-shirts
Boxer briefs
One Sweater
Top Coat
Wool dress pants

Some have said that it’s what’s on the inside that counts, and this is only partially true. I’m referencing what you’re wearing underneath those clothes that people can’t see. Let’s start with the white t-shirt.

White t-shirts come in many shapes, sizes, and prices. I’ve worn the $2.00 t-shirt and the $50.00 t-shirt. Could I tell a huge difference? Not really. Your standard, national brand, multi-pack t-shirt will be in fine.

What is important about a white t-shirt is that it’s fitted, meaning it holds close to your body and isn’t super baggy. Further, it should be a standard crew-neck, not a v-neck t-shirt. You will always wear these white t-shirts underneath your dress shirts, sweaters, etc. They are essential for a variety of reasons. First, some dress shirts (both cheap and fine) can be quite thin, and without the white t-shirt, someone will be able to see your skin underneath the shirt. The white t-shirt will bring out the natural color in the dress shirt and will shield your skin from being seen underneath the shirt. Further, for those of us that can sweat when we’re either overheated or nervous (or both), the t-shirt will be the first line of defense in absorbing sweat. The most unsightly sweat comes from underneath our arms, and this also has the potential to stain and ruin a dress shirt. But obviously we don’t just sweat underneath our arms, and if your dress shirt looks like you’ve been working out in it from the amount of sweat that’s coming from your chest, you’ll certainly be sending the wrong message to the girl you’re with… unless you two are engaging in a physical activity that would require such perspiration.

A nice pair of jeans is something that can not be missing from your wardrobe. Whereas you can can buy the $2.00 white t-shirt, good jeans typically range from $50 - $200. Don’t skimp on the jeans. They can be worn with your favorite sweat shirt, with various types of dress shirts, and with or without a sport coat. This will be the most versatile - and most worn - item in your fashion artillery. The color of these “blue” jeans should be a moderate blue, leaning towards a gray hue if possible. Avoid colors that are extreme, e.g. very dark blue or very light, almost white colored jeans.

As mentioned, I will be covering other essentials over the next several weeks and helping you make Timeless Trendy a part of your lifestyle. In the meantime, what do you consider an “essential” in your wardrobe?

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