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Know When to Walk Away: Avoiding Menswear Remorse

August 5, 2011

We’ve all had our moments. That sale on Gilt where we are watching the 10 minutes click down and we are actually convinced that the Rick Owens pants look good. Or when we believe that the unconstructed jacket on eBay that doesn’t fit in the shoulders somehow will when it arrives on our doorstep. Or that we really need that 8th blue oxford shirt that is on sale because we believe it is somehow different than the 7 other hanging in our closet at home. At times everyone gets lost in the moment and forgets that sometimes it is better to simply walk away.

I’ve been talking with a good friend who has a footwear collection that exceeds my own about knowing when not to make a purchase and it made me realize that for those of us who enjoy the sartorial arts, the menswear game can be quite an addcitive one. Indeed anyone can be a buyer but it takes wisdom to know when not to pull the purchase trigger.

Certainly no one bats when acquiring his habiliments but we should all strive to be better in our accumulation of gear. Less can indeed be more and I don’t know about you, but I sure as shit don’t need another repp stripe tie, anymore raw denim or another pair of canvas sneakers.

But how do we really know when to walk away from a purchase? Here are some rules I try to go by when I go buy.

Rule #1. Don’t Buy Anything that Doesn’t Fit (that can’t be tailored): This is the easiest rule of all. If it doesn’t fit and it can’t be easily altered to do so, exit stage left. Is that size 42 jacket a steal at 75% off? Yes it is. But if the shoulders don’t fit now, they never will. Are those XS shirts on sale tempting? You betcha. But unless you are really an XS, leave ’em for the next (really skinny) guy.

Rule #2. Be Careful Concerning Brand Loyalty: Even amazing designers strike out sometimes. Don’t be the guy so brand loyal that he can’t differentiate the good from the not so good.

Rule #3. Don’t Go for the Overly Trendy: Just because you have seen it on all the celebrities on GQ’s This Week In Style doesn’t mean you should be wearing it. Look, Justin Timberlake can wear gear you and I just can’t pull off. He probably has people giving it to him to wear so guys like us will be tempted to run out and spend major $$$ on the clothes he is wearing. And to be honest, even if he is buying it, JT has the cash money to waste on trendy garbage. You don’t. Save your hard earned money on the classics, leave the trendy on the rack.

Rule #4. Be Wary of the Buy One Get One 50% Off Sale: This one’s an obvious trap. Sometimes you don’t need two… sometimes you don’t even need one.

Rule #5. The Danger of an Expensive Designer, Highly Discounted: Just because it is on sale and it’s Jacobs by Marc Jacobs for Marc by Marc Jacobs in Collaboration with Marc Jacobs for Marc by Mark Jacobs doesn’t mean it should be coming home with you. Plenty of the stuff high end designers make barely even looks good on the runway and there are no real life situations that will warrant you wearing it. Thus when you see that Thom Browne Fringe Man Skirt a couple years from now marked down to $63… just don’t do it.

Rule #6. A Good Store Doesn’t Equal Good Purchase: There are some great menswear stores out there which keep most of us menswear fans geared up and our credit cards maxed out. Just don’t be fooled that you need everything from that store or that everything from that store makes for a great purchase.

Rule #7. Don’t Try to Keep Up with the Joneses: Know yourself, know what you like, #&@% the Joneses.

Rule #8. Remember If You Already Own It: So you see that OCBD’s are on sale at (fill in the blank place you like to shop) and you end up picking up a couple while your lady is in Anthropologie. What you forgot was that you literally already have the same shirts at home. Sure, a man needs plenty of OCBD’s but you have enough for everyday of the week and twice on Sunday. No wonder you liked it… you already have it.

Rule #9. Don’t Avoid the Big Purchase: It’s your birthday/holiday/great aunt left you an inheritance and you got some extra cash to spend. Think of investing it in a big purchase for which you wouldn’t normally have the loot to afford (aka navy blazer, amazing footwear, great leather travel bag, that perfect suit you’ve always wanted, a vintage timepiece, etc). Don’t waste your purchase power on lots of inexpensive attire you will never care to wear. Unless you are starting from scratch, you shouldn’t continue to accumulate repeat items before you get your hands on some timeless ones. Don’t be afraid of the big purchase. Sometimes it’s expensive because it’s flat out better.

Rule #10. Don’t Listen to the Salespeople: When your job is to sell something, the odds are you’re going to try and sell something. Makes sense, right? That being said, why would the lady at Bloomingdales have any reason to tell you that the shirt you are trying on doesn’t fit you right or that the pants make your ass look weird? She doesn’t. Truth be told, there actually are a few storehouses where the good folks working there do a fantastic job in telling you the truth concerning their products on your frame. Just keep in mind that those places are the rare exception to the rule that salespeople are there to sell. Know yourself, know what you like, #&@% the salespeople.

Rule #11. Be Attentive at Outlet Malls: Look, I’m not saying that you should never find yourself purchasing items from an outlet, as sometimes you can find some of last season’s greatest gear for a song. Just remember, there is a reason it is at an outlet and not somewhere else. Many larger brands (J.Crew, Brooks Brothers, Banana Republic, etc.) have an “outlet” brand variety that is typically lesser quality than the store brand. Some outlet shops carry damaged products, have items that were just too damn ugly to sell (see An Expensive Designer, Highly Discounted) and even try to trick you into thinking you are getting a good deal by buying more (see Buy One Get One 50% Off). If you do decide to make the occasional outlet purchase, just be sure you know what you are doing and you know what you are getting.

Rule #12. Don’t Buy Because A Blog Told You It Was Cool: At the risk of annulling all you just read, don’t always listen to bloggers. Plenty of us are loud mouths who are highly opinionated about things that make little difference in the real world. More than half of the time you can bet that we don’t know what the hell we’re talking about. Let’s just hope that this post is that small percent of the time I just might be right.

Got your own rule to add to the list? Add it to the comments to help us all know when to walk away.


22 Comments leave one →
  1. August 5, 2011 9:39 am

    Ask yourself when you’ll wear it: I know I’ve seen some super cool items (bright suede shoes, patchwork blazer/shirt, etc), but it’s not worth shelling out big cash for something I’ll wear twice a year (unless we’re talking a tuxedo or something else that I’ll rock for the next 20 years). Living in Maine also makes some clothing very seasonal. I don’t like spending a couple hundred on something I can only wear three months out of the year.

    • Rafael Ramos permalink
      August 7, 2011 9:20 pm

      Completely agree. Living in Maine myself makes wearing certain bits of clothing very difficult to pull off unless I was somewhere a little more metropolitan. Know your surroundings.

    • August 7, 2011 10:13 pm

      Wise addition.

  2. dmisaacs permalink
    August 5, 2011 12:23 pm

    Wise words. I’ve been in the process of re-creating my wardrobe for the past couple of years, and before I buy something, I assess what I already have and think about the gaps in my current collection. Then when I shop, I just try to fill the gaps with good versions of the things I want. When I am targeted like this, it keeps me from buying things on a whim that I will only regret later. I’ve given away too many pieces that sat idly in my closet for months, or even years, and I hate wasting money.

    • August 7, 2011 10:15 pm

      Makes good sense.

      I often find myself drawn to blues in shirts and brown (of course) in pants, which leaves me lacking in many other areas.

      I like the idea of buying with purpose as you suggest.

  3. August 6, 2011 9:18 am

    J, this was great! #12 made me think of that ever so typical comment on blogs that goes, “…you do own a _______, right?” Well done.

    • August 7, 2011 10:16 pm

      Haha. I figured most other menswear bloggers would get a kick outta #12.

      Thanks for the kind words my friend.

  4. August 7, 2011 6:10 pm

    This is an outstanding post, J. Look for a follow up on RCS this week.

  5. August 7, 2011 9:30 pm

    Fantastic piece for men like myself who sometimes need to know when to stop shopping.

  6. Sean permalink
    August 8, 2011 2:33 am

    #11. Some of the larger brands do make a “cheaper version” of there brand specially made for the discounters but Ever since the economy turned I would have to guess 90% of designers “now” send there leftover stock too off-price stores and to make it even worse they sell it at nearly the same time it’s in the regular retail stores. The way they keep this hidden is by only placing a very small amount of units per door and there’s way more discounters than retailers these days. so if you see a full rack of seven diamond (bro club) shirts and maybe one or two “good designer” brand shirts, Your possibly scoring a deal….but you never know. It’s a shady menswear game out there ha ha great article!!

  7. August 8, 2011 11:37 am


    I mean there’s definitely truth in this, man, zero doubts about that. Personally, I’ve been working on trimming the fat, cleaning out my closet of the stuff that I’m just stockpiling and never really wear in order to sell it or simply give it to Goodwill for someone else’s benefit.

    To be honest, I’m finding that all I really need is a small, closely edited wardrobe of versatile, and most importantly, high quality items that keep you looking smart and fresh. Being impulsive with your purchases is simply ill advised, and I think it’s also important to realize what’s a trend piece and what’s actually going to give you true value in the long run. But yea, definitely a great write up, man, I’m right there with you. I appreciate the thoughts!


    • August 8, 2011 5:06 pm

      Truth in the keeping the closet mean and clean.

      I move through mine a couple times a year and rid myself of anything I didn’t wear in the past year. At times it means facing the hard truth I made a poor purchase and letting some items go to the consignment shop, but c’est la vie.

  8. August 8, 2011 3:17 pm

    Excellent post. While most style sites focus on what to buy or what they want, this is a great piece on determining if you need it, to show some caution. I’ve shared it with our readers as well, thanks!

  9. Dano permalink
    August 8, 2011 4:54 pm

    I wish I read this like 3 months ago before I went broke :) Great article!

  10. August 9, 2011 7:47 am

    Came across this post from valetmag, agree with you 100%. I would also concur with the person who spoke of versatility. If I can wear it for work AND for play, simply by unbuttoning a collar or changing shoes, that’s a plus. Also, fit is becoming a main focus for me now, before I had a collection of too big BDs, now I’m in the midst of tossing those in favor for ones that don’t look like my older brother’s shirts. Great work.

    • August 9, 2011 8:35 am

      Cosign on versatility my friend.

      Glad you found AHD on Valet. Hope to see you back around these parts and thanks for the kind words.


  1. How to Buy Clothes You Need

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