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Prior to owning Theodore 1922 I had a business organizing people’s homes and closets. My company was called the Space Liberator a name I felt really captured the goal of my company: freedom from clutter and dreck. Here’s my silly logo:

My clients closets were often quite out of control….both men and women alike. But I discovered that men in particular really like to hold onto old clothing. Like a glacier from which you glean info about years gone by, these closets told stories that were sometimes decades old…layer by old unused layer.

Ones closet should not be a time machine or a walk down memory lane. Remember, it’s a closet, not a museum.

The most useful closets help you spend as little time thinking about your clothing as possible because everything has a purpose. A healthy closet houses current clothing that makes you feel your best and sets you up for your A-game. It’s easy to navigate on work days, weekends and for special events.

I no longer have time to Space Liberate but still I feel the need to help, having heard many times how frustrated you are by your closets.

So! I have condensed some very basic rules for the guy who’s closet has gotten out of control. For some of you, these tips will be too basic. For you I am working on a more comprehensive check list. But if you are a guy who has an overstuffed, frustrating, booby trapped closet you will benefit from these tips.

I highly recommend executing the actions….even if you feel it’s a waste of time. The amount of satisfaction (as well as time and money savings) to have a closet that works for you is immeasurable.



I know it sounds basic but if you don’t make a date, it’s not getting done. That being said…don’t schedule too much time! Biting off more than you can chew is a sure way to foster procrastination. Try hour long chunks. And here’s the kicker: set a timer. Would you start a meeting at work that had no end? Would you watch or play hockey if there were no time limit!?! Sheesh, no. So set a timer for organizing too. It helps to see how much time has passed and how much you can get done in the 60 mins.


You can’t organize your entire closet in 60 mins, especially if this is your first time doing a clear in (forever?) a long time. You are going to have to decide what is most important. Is your sock drawer overflowing with expired goods?

Got gag boxers still hanging around from your bachelor party?

Are your ties more like a lair of snakes? Maybe you want to tackle suits and shirts! Decide what will give you the most satisfaction and do that thing. In fact, write your chunks down (A chunk would be “suits”, for example. Or sweaters. Dress shirts. T-shirts. Socks. Outerwear etc etc). Don’t waste your hour deciding what to do next cuz you may surprisingly finish sorting your hole-y, stretched out socks from the ones that stay up in like 15 mins. And you get to check that chunk of your list. Only you know what is really disrupting your closet so the list is important. No one can tell a Space Compromised client what isn’t working.

Keep this list close to your closet area (in a drawer or tacked up on your tie rack) so you don’t have to do this step again.


Only you can answer these questions but they are the questions I’ve asked Space Liberator clients as they tackled their wardrobes.

Is this stained? This is the easiest one. If it’s stained, ripped beyond repair, snagged or ruined throw it the eff out. Not even the Salvation Army wants stained clothing and neither should you.

Do I like this? Not “I should like this”. Not “I spent a lot of money on this so I should keep it.” No. Ask yourself if you really like it. Now, this may require some effort because you are probably going to have to try it on. It might look good (or bad!) on the hanger but does it look good on YOU. Do you love the image it projects? This is very very important. If anything gives you low self worth or reminds you of a meeting that went horribly wrong or itches or is too tight anywhere..donate the eff out if it. It will look good on someone else and it’s useless to the world just hanging in your closet. Liberate that space!

Does this fit? Seems pretty elementary but if something has been hanging for anything over 12 months you MUST TRY IT ON. Because there’s got to be a reason why it’s hanging and not working for you. Every day your clothing should be working for you and if it’s not, gather the freeloaders and question why they are squatting in your closet. So, does it fit?? If not, donate the eff out if it!!

And finally: Here is a list of things I can absolutely guarantee you can get rid of/donate without having an ounce of regret. Actually, I’m going to take that a step further just so you are not tempted to keep a “maybe when” pile: you don’t need them, they are OLD, they are TIRED, they ARE NOT COMING BACK:

Pleated Pants: not coming back in any incarnation you have in your closet. Yes, there are some pleated pants but the pleats are sewn in tight, so do not add volume. Still not sure? Would you wear a pair of pants from the 1940’s to work? No. Because even though fashion might be inspired by the past it never 100% replicates itself. So no, Versace isn’t going to say “Hey Let’s do exactly what we did 20 years ago!!” It just isn’t going to happen and that fact needs to be faced.

Sure, this guy is pulling off pleated pants and if you are going for a hipster look, rock on sister. But I am talking classic working gent here which these 2 guys are clearly not.

If you are a larger guy…I’m talking quite beefy…then you may need a pleat for the extra room. But even my beefy guys have mostly moved over to a flat front pant as the look slims them down. This is going to have to be your call. At least try a pair of flat front pants on in a store to see how they feel…can we at least agree to that?!

Box Pleat Shirts: This is the one with the pleat at the back. It cannot be tapered, it will always be big at the waist. Again, this is for really burley guys who just can’t fit a shirt without the pleat. All others, see the notes on “pleated pants”.

Suits or Jackets That Don’t Fit Your Shoulders: If you can grab a finger and thumb full of fabric at the top of your shoulder then the jacket doesn’t fit. Perhaps you slimmed down. Or maybe you were buying jackets to fit your waist instead of your shoulders (something the sales person should have talked you out of).

Most garments have enough fabric to let out the waist but it is impossible to take in the shoulders.) Whatever the reason, move on from the mistake and get garments that fit well.

Pants That You Can Grab a Handful of Fabric at the Crotch/Seat (from behind): You can lose 15lbs off your silhouette just by buying slimmer pants. Baggy pants weigh you down. I have been preaching this for 7 years now and thankfully even the die hard baggy pants-ers (you know who you are!) are converting to slightly slimmer styles. Listen, I am not talking Queen Street West skinny here. But do you really think George Clooney would make the girls swoon so much if he had on saggy pants. He dresses like a classic gentleman and there’s no reason you shouldn’t either.

Ok, phew…that’s a lot of questions and deciding! This is the meat of the work here folks. It requires some work getting answers but remember, it’s only an hour and a chunk of your closet at a time.


Seriously? Yes, seriously. Decision making is actually physically demanding. There are some interesting studies on how food impacts our decision making. It’s why I always take snacks with me on buying trips. I dont want to get decision fatigue when making many important decisions in such a short period of time. So set yourself up for success and eat a healthy snack just before you start.


Custom clothing: Custom, tailor made clothing is a dying craft. At one time even PanAm pilots got their uniforms custom tailored (I just saw Catch Me If You Can again).

Those days are long gone. Fast fashion is taking over and although there are still Italian tailors working here in Toronto, they won’t be around forever. It actually surprises me that more men don’t flock to Made to Measure events because it is such a dying art and you should get it while you can. The long and the short is, if you have anything custom made for you I would say keep it…for now. Unless your entire wardrobe is custom and you plan on restocking your custom pieces seasonally in which case, donate your old stuff you lucky dog! But if you went the distance and got a custom suit for your wedding or for a special occasion and it’s not stained, worn and it fits then don’t get rid of it.

If you don’t have a custom suit or jacket then I’d suggest you get one stat. Like I was saying, one day Italian tailors will be a thing of the past and you want to be able to say “I got this made to fit me. It’s custom, no one else in the world has one. That was back when clothing came in stores and not delivered by a drone.”

Ok, the future might not be all that bad…but you never know!


We all have items we just can’t get rid of whatever the reason. That’s ok! As long as it doesn’t become every other ill fitting garment this is perfectly normal. There are a few things you can do to limit the amount of space these Museum Pieces take up.

-literally limit them by buying a container. This is your Memory Lane Box. Put your varsity jersey in there. The last pair of socks your grandmother gave you. Stuff like that. Once it’s full it’s back to decision time of what stays and what goes.

-take a picture of the item in use. Take one last photo of yourself and your wife in your wedding suit…no one needs to see that it doens’t do up at the front! Take the pic then frame it.

See, then the garment is back living out in the world, free from the dark closet. Go one step further and get a session with a professional photog! Boy, closet AND relationship advice in one column!!

-give it to someone you see on a regular basis. Maybe your best buddy would like that polo. Got a kid who will almost fit that groovy t-shirt? Ask them if they want it. Some of my best clothing items growing up were pilfered from my parents closet…my moms and my dads.

-and finally the old standby: Put the dreck in a box and write the date on the box. Seal the box. If in a year you can’t remember anything in sealed box, take it straight to the donation place. Do not unseal. Do not unseal. Do not unseal!!


It’s not easy sorting closets but it’s very rewarding once it’s all done. And keep in mind all the people who are more needy than yourself who will be very grateful for your donation.

Have fun!

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