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A guide to help the average man... look less average

Altering old baggy clothing

Mark Kwak

A lot of my friends ask me for advice on what to do with their old clothing that just don't fit anymore. The process usually goes a little something like this:

1. I peruse my friends' closet.

2. I'll see a piece of clothing that looks God-awful and ill-fitting.

3. I'll say "toss" without a second thought.

4. I move onto the next piece.

At this point, my friends will stop and cringe, hesitating to move on. And of course I get it. What if the piece I'm tossing is actually a $175 shirt? Or what if it's the most comfortable piece of clothing in the entire closet?

As a result, we get hung over the piece for several minutes, trying to decide whether it stays in the closet or goes away to Goodwill.  Then we ultimately have to come to a compromise. And almost always, my compromise is this - get it altered so that it doesn't look ridiculous.

So I wanted to quickly speak about this compromise. "Getting it altered" is an easy way for someone to make a piece of clothing look better without having to spend a ton of money. Why replace an entire wardrobe when you can go to your local tailor and have them stitch up your current wardrobe to look perfect on you?

Now, I'm all for tailoring your clothing to look good, but I will say right now, sometimes it just doesn't make sense. Here are the situations that I come across where you shouldn't bother.

1. Dress shirts that are simply far too big.

Dress shirts are usually the easiest pieces of clothing to alter. However, if the original shirt being altered is two or more sizes too large, it may be a bit of a challenge. Here's why: it is very difficult to alter the shoulder hems on a dress shirt, and the shoulder hems are the most important part of the dress shirt fit. If the shoulder perforations are hanging at your mid triceps, you're likely going to encounter baggy sleeves, baggy mid sections, and too large of a collar as well.

First off, there are just too many alterations. Second, if the shoulders don't fit, no matter how well you alter the shirt, it won't look good. Toss it.

2. Boxily (is this a word?) designed clothing often cannot be altered to look fresh and fit.

Boxy clothes are often designed to give you a more relaxed fit. Take for instance a boxy blazer. You know, the one where it feels like you're swimming in the extra space? No matter how good your tailor is, the boxy nature of the blazer will make it difficult to get it to a trendy and form-fitting spot. It's not just about the extra fabric, but it's also about the balance of the jacket from top to bottom design-wise, and making a couple cuts here and there won't work. Toss it.

3. Some pieces just aren't meant to be altered in certain ways.

Think about a coat that is too long. Or a pair of jeans that are too baggy. Both of these could technically be altered to match the fit you want. However, let's say there are a bunch of pockets on that coat from top to bottom, and the jeans are baggy in not just your legs, but also your butt and crotch regions as well.

In these cases, it's likely that the tailor won't be able to alter your clothing to look better. Instead, you'll end up with a warped and unbalanced look that will force you to toss the pieces anyway. Make sure to look at your clothing holistically before making any alterations, and decide whether it makes sense. If not, toss it.

Okay, this is making me sound like I don't recommend people to go to a tailor. Not true in the slightest. I go to a tailor all the time, and it's invaluable having a good one.

All I'm saying is that sometimes it's just not worth it. It's all a cost/effort battle. Are you willing to take the financial hit by tossing the piece, or would you rather work hard and pay a lot of money to get it to look decent? Sometimes it's worth it, but I'm saying that sometimes... just sometimes, its irreparable and not worth the effort. In those cases, be okay with donating your clothing. Perhaps someone with a more suited body-style can inherit your clothing, and wear it the way it was supposed to be worn.