Wing Tips: Your First Time…at the Tailor
Jennifer was shocked to hear that many of our readers haven’t been to the tailor. Not only that, but most are nervous about going: what will they do? What do they need? How do I know I’m getting the right work done? With a little push from Elle (who hasn’t been to a tailor either) Jen decided to write up a few tips on finding, going to, and working with a tailor. This is Part Two: Your First Time…at the Tailor. Just in case you missed it, here is Part I: Finding a Tailor.
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My Most Recent Experience with the Tailor
I took two pairs of pants to the tailor on a random, work-filled Tuesday. Here’s what they needed:
- 7 for All Mankind Crystal Dojo Jeans: I bought these beauties on Gilt.com for cheap, but knew the 35-inch inseams would need a hem, big-time. (Side note: Wash and dry your pants as usual before hemming them, to avoid uneven shrinkage. More on this later.)
- Kut Denim
: My tried-and-true Kut jeans (which I first posted about here) have started to wear out at the seam of the inner thigh. Instead of throwing them away, I decided to have them patched: the tailor will attach a piece of denim on the inside of the jeans to reinforce them. That way, I can wear them another few years before they give out completely.
Here’s how my initial trip to the tailor – a tailor I’ve never been to before, I might add – went down:
I walked in and explained that I needed a pair of jeans hemmed. The tailor offered to measure and pin the hem for me, or have me show him the length I’d like them hemmed to. Because I already knew the measurement (about two cuff lengths) I was able to circumvent the process of bringing the right shoes, trying them on, worrying about whether I was standing up straight, having them pinned, and taking them off again. Easy!
I then pointed out the sorely-needed patch job on the Kut jeans, and he deftly marked the location with a piece of red tape. After trading my name and phone number for a pick-up date (that Saturday – fast, since I’d brought them in Tuesday) and price ($26 total) I was on my way.
When I came back, it was the same no-nonsense situation: I gave them my name, got my stuff, was shown exactly what they did, and paid the bill. Receipt in hand, I went home to try my Sevens on – if I’d had the right shoes, I would have done so before paying – and kept the tailor’s number handy in case the stitching blew on the Kut Denim when I washed them. When all was well a week later – after a couple of wears and washes – I tossed the receipt and wrote a glowing Yelp review.

Before hemming, and after. In other news, I really need a haircut.
You & The Tailor – It’s Not So Bad
Going to the tailor – especially the first time – takes a little planning. Use this checklist to make sure you’re not caught off-guard when the proverbial pins are in the pants:
- Run the garments through their usual wash and dry cycles before you go. You don’t want to hem those pants to the perfect length, only to find them a half inch shorter the next time you wash them.
- Bring your heels. That is, if you want your pants hemmed to heel-height. I go to the tailor on “comfy days,” and if I’m having a pair of slacks hemmed to accommodate three-inch heels, my Skechers just won’t do.
- Wear the right bra. I could talk for hours about the importance of a well-fitting bra, but I’ll save it (for now). Let’s just say that if you wear your t-shirt bra to the tailor, and you’re having that dress with the plunging neckline taken in, you could be in for a world of hurt.
- Know the look you want. Do you want the tailor to use the same kind of cuffs that your jacket originally had, or just something basic? How about using the original, designer-frayed hem of the jeans you bought, only three inches shorter? Would you like a horizontal hem (straight across) or do you want it to come up a little higher in the front, so your shoes peek out? (I love this look, by the way.) If you’re nervous, just tell the tailor you want the same thing, just so it’s fitted to you. That makes it a lot easier.
- Be prepared to pay up front. Some tailors (and cobblers) request that you pay for their work up front. They’re not trying to screw you out of a dollar – I promise – and if they screw something up, they’ll fix it or refund your money…sometimes both.
Here’s the biggest rule for going to the tailor:
Accept yourself – your weird waist, your fat rolls, your uneven stems – and don’t try to hide who you are.
When you compensate for your “flaws” you make everything the tailor does totally worthless. When he’s hemming your jeans, stand naturally – because that’s how you’ll always stand in these jeans. When he’s pinning a dress, don’t tense up – it changes your proportions, which means you’ll still be uncomfortable in it, but in a whole new way. A trip to the tailor is a lesson in total self acceptance, in letting yourself be who you are…and letting your clothing show that off.
Which is why it’s totally worth the trip.










I adore you, Jennifer Nicole. A helpful, informative post on dealing with tailors that includes a shot of body positivity? Could you rock any harder?
Sally´s last blog ..Femininity and Athleticism
In case anyone in NYC is reading this, I recommend Jean at Ghost Tailor. I would never go to anyone else! Info here: http://wendybrandes.com/blog/2009/04/ive-seen-ghost-tailor/
WendyB´s last blog ..Most Awesome Designing Women OF ALL TIME
A good tailor really can make a world difference. whenever i get compliments on something looking “tailored for me” funny enough those are the pieces i actually did take to my tailor.
a big thing with a tailor (a cobbler too), is to find one through word of mouth. ive had some things ruined when i was trying to find one on my own.
I always pay in the beginning. Then I don’t put off picking up my things because I don’t have the cash, and yes, the tailors I’ve been acquainted with seem to prefer cash. Given that their fees seem reasonable to me I pay cash and don’t fret about it.
They’re often upstairs from a dry cleaner if you are out wandering around looking for one!
I’m big on having the sleeves of jackets shortened. In fact, I’ve begun tisk-tisking women I see with their jacket sleeves rolled up because I know they’ve done that instead of taking themselves to the tailor!