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As noted in the products you shouldn't buy cheap question, you should buy quality, long lasting clothes. Where can you find quality clothing and how can you recognize quality clothing in discount and thrift stores?

A corollary, "How do you extend the life of this clothing?" is even further afield from Personal Finance, even if it could fall under the category of maximizing personal economy.

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On the quality angle a big part of it is experience, but the biggest thing is careful observation. You have to take a close, critical look at any article of clothing. (This holds true for just about any purchase.)

  1. What is the quality of the fabric? (This would include bstpierre's point about the color fading and washing instructions.)
  2. How about the stitching?
  3. What about any design or embroidery? (This also goes to avoiding fad topics, which may very well kill your desire to wear said article even if it is still in good shape.)

As far as finding them for reasonable prices it's the usual thing: sales and buying them second-hand.

Finally, regarding maintenance:

  1. Don't wash them too often. (This may sound gross, but sometimes unwashed does not equal dirty.) The best way to deal with this is to have a sufficiently large wardrobe and to rotate through it consistently.
  2. Wash them in the coldest water that is reasonable. Basically, avoid hot for anything that is not underwear or seriously dirty.
  3. Also, be careful with your clothing. Don't crawl under the car in your Sunday best. Be mindful of what you wear around the house.
  4. I almost always wear a white t-shirt as an undershirt.
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The idea that you should buy quality, long lasting clothes shouldn't go unchallenged. It's just not true for everybody. If you have a job or a lifestyle that makes it so your clothes are going to get worn out fast regardless of quality, buying expensive clothes doesn't make sense.

With that said: look for heavier-feeling fabrics, avoid colors that will fade (or worse: bleed into your other clothes in the wash). Check the laundry instructions so you can see whether they're on the delicate end of the spectrum.

Re: how to extend the life: avoid bleach. Even color safe bleach contains peroxide which can break down fabrics faster.

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Use resources like Consumer Reports and recommendations from like-minded friends to figure out brands which have a reputation for making quality clothes. Then trust, but verify.

Ideally have a friend who sews a lot go with you on a clothing expedition if you don't know how to determine quality in clothing. People who sew knew their fabrics, and this could be very helpful to you. Start at places that are known for quality clothing, but make sure the reputation hasn't outlived reality. I'd look for:

  1. A fabric which isn't overly prone to wrinkling by bunching it in your hand and squeezing hard. The fewer wrinkles, the better. Even if you like ironing, there are gradients within clothing that requires ironing on how wrinkly it is. Cheap fabrics are sometimes worse.
  2. A thick fabric (generally will hold up better, although something like linen can be quality and is light for summer)
  3. Stitching which seems solid (you don't want to see a lot of hanging threads - that's a sign of poor workmanship).

Once you've identified places that you can trust, wait for sales at those stores. I've found that shopping sales at department stores (or better, places like L. L. Bean) is cheaper than a discount retailer and much easier. Even cheaper, go to a thrift store and look for those brands in timeless styles. Your mileage will vary in terms of the what people throw out in your area. Thrift stores work extremely well in high cost of living areas where people give away nearly new items.

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Are specific brand recommendations allowed? I'm a big fan of Lands' End. They have good quality clothing at reasonable prices in all the basic styles. They have great customer service and you con order online and avoid clothes shopping at the mall (which I hate).

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According to this http://shine.yahoo.com/event/financiallyfit/cheapest-days-to-shop-online-2301854/ Tuesday is the best day of the week to buy men's apparel.

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The best way to find good quality is to check the garment tag: What kind of material is it made of? Jersey 100% cotton or any 100% cotton is one of the best quality material for most casual clothing.

Then, you should touch it (designer step/touching). You will get better along the way. If you think you will like it, it may be a good quality. You should try it. and look for similar material when shopping. It does not matter the store where you shop, you should check the garment quality because even at the expensive stores you can find bad quality.

Quality in Stitch: you should check the the garment stitch, look at the top and underneath stitches, watch for good and consist stitching pattern. especially the sides and armholes underneath of the garment.

Style is something personal. Everybody has different style, but stores are classified by age targeting. If you can find a store that usually made your style, good quality material at reasonable price. you should consider shop there. Most of the time, it will cost a little bit more or much more. BUT CHEAP IS EXPENSIVE!! you end up spending more money at the end of the year.

Reasonable means a fair price for both parties, You and the seller. Neither cheap or expensive.

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