Dressing for Success

A few weeks ago, I had dinner with my parents, and it was right after I got back from Colorado and the fencing program. They said I looked great, they praised me to the skies, they said all sorts of nice things, and they bought me a very nice dinner at a very nice restaurant.

At the end of the night, though, they got honest. “You look great. Your clothes look terrible.” I was indignant, but they were right. My shirt was all wrinkled and bent out of shape, my pants were stained in places, and the hems were ripped. The were also unflattering to a man of my build and proportions.
Going through my closet to prepare for the first days of school, I discover that what my parents said about my clothes that night applies to much of what I own. It seems that I am afraid of good clothes. I own a lot of stuff from Old Navy, which does not hold up to the kind of uses to which I put my clothes. I have too much ‘festival’ clothing which I hardly ever get to wear, and not enough of the clothing that I use on a daily and weekly basis, like collared polo shirts, dressy button-downs nd suits. I have too much underwear (some of which needs to be thrown away), and not enough pairs of socks (and not enough athletic socks compared with dress socks). I have three pairs of shoes that look crappy, and a couple of pairs of boots that look even worse. There are several pairs of jeans or shorts that don’t fit me (and look terrible on me even when I do lose the pounds to wear them). Half of my ties are stained and not really good for regular use. Many can’t be cleaned, and many more are wrinkled.

Mom told me I should go through my clothes and find a lot of stuff to throw or give away. She wants me to be ruthless. Torn cuffs on pants? Toss ’em. Threadbare collars on shirts? Shred ’em for rags. Highly visible stains? Throw them out? Worn in places and unflattering? Give to Goodwill.

It’s a little horrifying how much of my wardrobe falls into one of the four categories just listed. But it’s not only that the older stuff is worn or damaged. I have a pair of shorts I bought only this summer that are already stained and look nasty. I have two nice Lacoste shirts, presents from my mom this summer, and both of them have indelible stains on the front or on the shoulder; both shirts are light colors, and one is white.

How do people decide what to wear, and when to get rid of something? When you get rid of something, do you take it to Goodwill or the Salvation Army or a consignment shop, or do you just throw it away?

Liked it? Take a second to support Andrew on Patreon!
Become a patron at Patreon!


  1. do you take it to Goodwill or the Salvation Army or a consignment shop, or do you just throw it away?

    In general if I’m culling clothing for any of the reasons you’ve mentioned (stained, ripped, worn) I toss them in the trash. I see no sense in me sending something that I consider “damaged” to any mostly volunteer organization for culling.

    If I’m tossing stuff because it no longer fits that is another story. If it’s in good shape I send it on to charity. Except the underwear. Never the underwear.

  2. Mmmm Clothes

    Ben here. My favourite line of clothing, pants-wise, is the Stain Defender by Dockers. They’re just regular khakis, but they have some sort of Teflon coating that literally makes liquids bead and roll off, just like on a freshly-waxed car. Usually Kohl’s is having some mega-sale on them, so you can get a pair for under $30. I have about seven pairs, natch. They also hold up very well under pressure. Happy clothes hunting!

  3. The aforementioned culling advice is good so I won’t go back over that.

    For procuring: I suggest evaluating the dress of your colleagues. Figure out what it is that you admire and/or disdain about the ‘looks’ of people around you. Their exact items are probably not going to work for you but it could help you figure out what general impression you want to strive for (or avoid). Once you figure out how you want to transition from the college-esque laundry pile look (which I’m not knocking cuz I’m most comfy in that too!) then you figure out what clothes get you there. Having a shopping buddy who is either invested in your look or is completely neutral (and therefore painfully honest) could be helpful. Um, is Mom an option? She’s obviously been thinkin about it!

    General inventory is a good idea. I like the 2-weeks-worth-available scheme. And, “ruthless” is a good goal.

    Good luck!

  4. A few tips from someone who has been replacing the majority of her wardrobe every 6 months or so for over a year now:

    If you are losing weight with any regularity, don’t buy good quality clothing in your current size. Even if you take excellent care of clothing (which, I’m guessing you don’t) re-sale value on everyday stuff is non-existant. Old Navy & the like are good for “temporary” clothing.

    Clothes to immediately trash: anything with visible stains or rips anywhere but on a seam.

    Clothes with rips on seams or missing buttons you can repair and keep if they are otherwise in good shape. These kinds of items can also be donated (Goodwill will do basic repairs).

    Again, if you are losing weight, anything too big goes. Anything unflattering or weirdly cut goes. It is okay to keep a few things that are in nice shape even if they are a little loose, but if it looks even moderately oversized, toss it.

    As for replacing, my policy is to have enough clothing for my everyday life for two weeks without doing laundry. I almost never go two weeks without doing laundry, but still. So basically, you need 10 days worth of work clothes and at least 4 days worth of casual wear (although I like to have a full week’s worth of that as well). Apply the same standard to underwear and socks.

    Good luck. My closets are due for a clean sweep as well, so I feel you on this.

  5. Re: It’s not a bad idea.

    You spend less time looking at you than your choice of companion does; pull a few dollars together and make an afternoon of shopping together. Let her pick the bulk of stuff out and play with the budget for it. It’s in her best interest to have you looking sharp, and it looks good to make the funds go as far as possible.

    What? Me, insightful about human behaviours? Banish the thought!

  6. It’s not a bad idea.

    I’ll have to think on it, though. I know that I’ve already gone through stacks and stacks of t-shirts, and tossed a great many of them. I’ve done the same with dress shirts and slacks.

    Actually at this point I’m more worried about what I’m going to wear, than what I shouldn’t wear any more.

  7. Me, I just turn my current girl loose on my closet. She is inevitably far harsher on taste than I am, and desirous of not only making me look better, but culling old stuff so she can establish appearance territoriality.

    Everything ejected goes to Goodwill; they’ll sort out the garbage so you don’t have to.

Leave a Reply

This site uses Akismet to reduce spam. Learn how your comment data is processed.