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1) Find tailors with high review ratings in your city. Search local review websites like yelp andcitysearch for "tailor" and "alterations". Extra points if there are positive reviews from other petite women. This is how I found my last favorite tailor in Los Angeles.
2) Ask other women. Know any perfectly tailored and well dressed women? Chances are these chic ladies have a fabulous tailor helping them out. This also works for impeccably dressed men. There's also a thread in the Alterations Needed Forum dedicated to tailor recommendations!
3) Look for tailors that advertise as specializing in custom menswear. Tailors knowledgeable in menswear tailoring should be able to handle your most difficult of alterations, no sweat. (tip courtesy of The Pocket Stylist by Kendall Farr)
4) Ask high end boutiques and clothing stores where they send their clients for tailoring.Most of these stores have a reputation to keep, so will work with the best of the best.
5) Skip the dry cleaner tailor. Unless all you need done is a simple pant hem, these tailors aren't as skilled as one who has their own shop.
6) Skip the department store tailors. They are often in a hurry, inundated with items, and disinterested. They won't take the special care with your garment a privately owned tailor shop will take. (Of course, there are exceptions. I've heard of ladies requesting specific tailors at department stores likeNordstrom that they know for a fact do a good job. I've never had such luck).
7) Ask to see a piece of their work. This is a good idea if you have lots of complicated alterations or expensive garments. Make sure the stitches look good, garment looks symmetrical, and that it doesn't look obviously altered. If a tailor shows you a hacked, misshaped piece of work, run away quickly!
8) Bring an easy, starter piece to be altered before you bring out the really expensive or complicated ones. Things like a pair of jeans that needs hemming or the waist taken in is good. That way, you can get a feel for the tailor's work, before handing over anything of value to get altered.
9) Talk with the tailor, not at them. Tell them what bothers you about the garment and ask them what alterations they think it needs. This way you can get a feel for just how knowledgeable they really are. The mistake I made at first was telling the tailor what I thought the garment needed, and never asking them for advice. They made my alterations, but I was never satisfied. Why you ask? I'm not a tailor! I don't know what a garment needs!
10) Make sure your garments are worth the cost of alterations. Don't spend extra money to get an item altered if it's going to have a short closet life. Avoid altering cheap fabrics or cheaply manufactured items. I've made this mistake, and ended up tossing tops I'd had shortened after only a few washes because they were cheaply made and ended up piling/fading like crazy. Never again!