Yes, I used to be fashion challenged.

In fact, seeing my choice of outfits in old photos sometimes makes me think this:

What was I thinking with that shiny "going out" shirt? I look like a MASSIVE bag of douche.

Now, I've never been fashion challenged in the way some guys are where they have no idea what to wear.

My problem has always been worse because I used to be one of those guys who always thought that what I was wearing was attractive to women (when it really wasn't).

Luckily, my problem has gotten better over the years through research and a LOT of female feedback.

It has also improved because I always ask myself these three questions before buying shoes, accessories, or any item of clothing:

Does It Fit Properly?

If there is one big takeaway you should remember from this post, it's this:

Fit is King.

Too many times I have wasted money on a shirt, pair of pants, or a jacket that looked cool on the hanger, but not on me.

For any of the trendy, name-brand items I bought, major alterations would not even bring the items to the point to where they looked good on me.

Too tight. Too baggy. Wrong fit on the shoulders. The sins were all the same.

To prevent these sins of poor fit, remember these tips:

  • Learn something about how clothes should fit your body type
  • Always try the item on in the context of a finished outfit (i.e., tuck in shirts, put shoes on when trying on pants, etc..)
  • NEVER be afraid to ask for a female opinion (e.g., friend, clerk, customer)

Of course, when it comes to fit, you should remember this most important tip of all:

Be honest with yourself.

Don't do what I did and tell yourself that the name-brand, cool style, or cheap sale price overcomes all.

I have seen guys in Hugo Boss who look terrible in their ill-fitting suits.

I have also seen guys in Banana Republic suits (1/5 of the price of Hugo) who get LOTS of stares from women because the fit of their clothes compliments their overall shapes (skinny and huskier builds alike).


Be like the second group.

Do I Look Good Wearing It?

This is the most important question of all but also one that may be hard to answer alone.

If you are like me and you cannot answer this question on your own, try this:

  • Get at least one female opinion after trying something on
  • Look for the speed of her reaction to what you're wearing
  • Stick with items that generate an immediate positive reaction

Sure, if a woman looks at what you're wearing and immediately says, "I like it" or "That looks good on you," then you buy that item.

Don't think. Just buy it.

If she says, "You look hot!" then buy two (in case the first one wears out).

If she has to "think about it," don't buy it. Or, return it if you already bought it (always keep ALL receipts).

The trick here is to have an open mind and trust the female opinion.

This is especially true if you are trying on an item that is not your normal style or something that you think doesn't look good on you.

For example, I once tried on a shirt and then heard a female friend tell me this:

I LOVE it. You look good.

The shirt had some pink on it and some touches that I thought were a little too "girly" for my taste.

I ended up buying that shirt along with a few others that day (that I picked out myself).

The next few times I wore the "girly" shirt, I got tons of compliments from other women.

Guess how many compliments I got on the ones I picked out myself?



If one woman likes the way you look in a new shirt, pair of pants, jacket, shoes, or anything, other women will like the way you look too.

Is It Worth The Money?

If you read any men's magazines, you sometimes get the feeling that expensive, high-end labels equal a more attractive you.

Sometimes this is true. Sometimes it's not true at all.

One reason I'm talking about price is that too often a high price tag often carries the illusion of better style.

Another reason is that saving money on some purchases will make it easier for you to stomach the higher prices on others.

For example, you might think that $200 designer jeans are better than a $20 pair from Wal-Mart and you'd probably be right.

However, just because you spent $200 on jeans does not mean that you are now ten times more attractive to women.

Of course, if you are watching your budget and spending $200 on jeans means you have nothing left for shirts or shoes, don't buy the overpriced jeans!

So, what's the bottom line with all of this? Simple.

Unless you are certain that it looks good and you are getting your money's worth, don't waste your money.

Price tags, sales, and name brands can all play tricks on your mind and the "Is it worth it?" mindset is a great workaround.

The beauty of this way of thinking is that you laser-focus your shopping only on items that make you feel good about how you look.

When you feel good about how you look, women DO notice.