The Tea on Tailoring

One of the most important benefits of working with a stylist is getting help understanding how to tailor your garments. So often, clients will want to get rid of perfectly good pieces of clothing because they aren’t wearing them. And they aren’t wearing them for 1 of 2 reasons - either they don’t know how to style the piece (ie: what to pair with it) OR the item doesn’t fit quite perfectly. If the latter, I often find that simple tailoring adjustments can make all the difference in making the garment more usable! As stylists, we can easily determine how a garment needs to be adjusted to make it look great on you. Here are some tips and teachings about tailoring your clothing to ensure a perfect fit.

The Case for Tailoring

As we know, all brands adhere to different sizing charts and as such, many people are not able to purchase things right off the rack and have them appear perfect (at least not 100% of the time). If you have some common sizing challenges (like you’re extremely petite or are larger chested or have wider hips than waist) then you are probably very used to making adjustments to clothing - but even for those who can often buy off-the-rack, tailoring is a great tool that can take your outfits to the next level! 

Do you ever wonder why celebrities on Instagram, on red carpets or in magazines look flawless in their clothing? Much of it has to do with the fact that they tailor their clothing to fit them to perfection. Common tailoring services include hemming the length of jeans or dresses, cinching trousers in at the waist, shortening sleeves, adding clasps to the bust and letting out seams - all of which can help your items fit you that much better.

For a small investment of time and money, you can walk away with a wardrobe that fits you like a glove. 

Where to begin?

Determining what needs to be tailored starts in the dressing room (or in the comfort of your home). First, try on each piece as you would style it (ie: wear the piece how you intend to wear it in everyday life, this is particularly important with hem lines). If you plan to wear a jacket over sweaters, you want more room so make sure you’re trying on as such. The consequence is that you may over or under alter the garment because you weren’t focused on the day-to-day styling. 

Once you try it on, it’s critical that you analyze the fit in the full-length mirror. First, take a look at the length of the garment! Are your sleeves covering any part of your hands? Are your jeans dragging on the ground? Are your culottes making you feel matronly? Is there a gap between my back and my jeans? Is your blouse pulling apart at the bust? These are all the questions you should be asking yourself as you determine the fit of a garment. If the answer is “yes”, the good news is that simple alterations can fix these little annoyances. You can use your thumb (or measuring tape) to estimate how much you need to tailor to get the fit right. 

I, personally, find it easier to “batch” my alterations. So I’ll try on a variety of pieces at once and then take them all together to the tailor. This lightens the time-suck and creates more efficiency. When at the tailor, you’ll try on every garment and you can give clear instructions on how you want the garment adjusted. If you bring in an estimated inch count that’s great, OR take recommendations from your stylist OR trust your tailor to know best (be cautious to not let them over-hem, you can take more up if needed). 

While some clients will take another garment for the tailor to compare to, I don’t recommend this as every garment fits differently. No hem length is created equal because no pant hits exactly the same as the other. 

A Note on Proportions

Creating a better fit for all of your clothing will help you create the right proportion for outfits and that is ultimately what creates a great ensemble. Here are some notes on how common garments should fit you!

Jeans - These are probably the items that need to be tailored the most and yet, I don’t have an easy rule of thumb. Every jean style is different and therefore, calls for different alteration. If your jeans are dragging on the ground (like a flare or straight leg) or bunching a lot (like a skinny), you’ll want to get them hemmed. I prefer my flares just about brushing the floor when wearing heels (creates elongation) and I prefer my straight legs hitting the top of my shoe. If wearing an ankle length (like demi flare or culotte), I prefer they hit right at the ball of my ankle. This ensures you can see a little bit of skin and the crop appears to be intentional. 

Skirts - if you bought a great slip skirt to wear this winter, pair it with your tall heeled boots to determine if it needs to be hemmed. “Midi length” items should hit between the knee and the ankle - most flattering when the length is at the smallest part of the calf. Dresses, like jeans, call for different length as they are all different styles. Similar to flared jeans, I think a full-length dress should just barely miss the ground (covering the shoes). Similar to midi skirts, midi dresses should hit at the calf. 

Jackets - The most common problem I see in jackets is the sleeve length. Jacket sleeves should hit right at the break of the wrist which is often a challenge for petites. Sometimes, a jacket may fit well in the arms and shoulders but be a little tight in the torso. If this is the case, they can let out the seams a little bit in the back of the jacket to create more space. That said, I don’t recommend buttoning a blazer or moto jacket so you don’t necessarily need to tailor to close.

All About Menswear


I cannot over-emphasize the importance of tailoring on menswear. While Men may have an easier job dressing (fewer options, more straight-forward) the thing that separates the well-dressed man is how he tailors every item to perfection. Because their outfits are so much more simple, the fit becomes so much more important! For example, if a 32 inch inseam on a 6’3 man is just a bit short, he might think he can get away with it. But is there anything worse than “flooded” pants? 

While men can often get away with not tailoring their day-to-day clothing like jeans and t-shirts, they absolutely should be getting all of their suits, slacks, and dress up clothing altered. There is no “shortcut” to being a well-dressed man! Because of the heavy need of mens suiting to be altered, I often recommend going semi-custom to begin with. When going to a specialty suiting shop and allowing them to fit you from the get-go, you’re actually saving time and money. Much like a stylist, a tailor at a custom suit shop is a specialist in the field and knows exactly what size you should be purchasing in each piece to minimize the need for tailoring. I see many men buying ill-fitting suits off-the-rack, only to then spend a fortune on tailoring to try to get the fit right. Trust the experts to guide you, even if it’s bit more of an investment. They’ll help ensure you look great and as we know with tailoring, the devil is in the details!

So, How do I Find a Great Tailor?

Again, the benefit of working with a stylist is they can make recommendations for great tailors near you. We know it takes a village to get your garments correct so we do our best to scout all of the professionals in your area. 

If you don’t have a personal stylist, good old fashion Yelp research is a great place to start! Most mom and pop tailors don’t have websites but many DO have Yelp pages - and the benefit is that you can see how others have experienced the business. I find it very helpful if the tailor has suiting and bridal gown experience. If clients have entrusted the business with their most prized garments, then I am more likely to trust their services. 


The only real way to test out a tailor is to take a garment and have them conduct some basic alterations. If you are happy with their due diligence (measuring, chalking, pinning) then they are likely reliable. Again, the tailoring experience is that much better when you know exactly what you want. 

A note on dry cleaners - I personally trust my local dry cleaner with simple alterations like hems. You can alway have your dry cleaner do your easy alterations and take more complicated needs to a specialist. 

Anything you can’t tailor?

While tailoring is a magical thing, unfortunately, there are things that cannot be tailored. Have a jacket that is too boxy in the shoulders? You are out of luck! Shoulders are the one piece of the garment that cannot be taken in or out so shop accordingly! 

Zippers in a moto jacket are extremely challenging to work around. While some tailors may be able to hem a sleeve with a zipper, it’s probably more costly than it’s worth. Special cuffs on the other hand are easier than they appear! It’s as simple as removing the cuff, hemming above the cuff and then reattaching. Knowing these small nuances will help you determine what you should/should not tailor.

Unfortunately, you cannot drastically take IN or OUT a garment (like changing it more than a size). Sometimes, a piece may be just a big snug and while you can often “let it out” - there is typically allowance only for about an inch. I only call this out so you don’t get your hopes up of fitting into a dress you wore 15 years ago. Tailoring is about perfecting a piece, not changing the fundamental structure of it. 

While there are a few cases (as listed above) where tailors cannot adjust pieces, you also should be cognizant that certain alteration services may cost more than the garment itself is worth. In these cases, I do NOT recommend tailoring. I am very transparent with my clients and let them know when it’s not worth altering a piece and the more acquainted you get with tailoring, the more knowledge you’ll have to determine whether or not a service is worth it. The worst thing you can do is get a $150 leather moto jacket and get $200 worth of alterations on it - for that much work and effort, you might as well have spent $350 on a better fitting jacket.

QUICK tipS

  1. Ask yourself if the tailoring is likely to cost more than the garment itself. If the answer is yes, IT IS NOT WORTH TAILORING (unless it is highly sentimental). 

  2. Bring the shoes! Make sure  you bring a pair (or multiple pairs) of shoes to accurately reflect how you will MOST wear the garment. If tailoring flared jeans for boots (for example) make sure to bring a pair of boots and not your low sneakers. 

  3. If you have “waist gapping” where you need a belt to avoid space between your skin and jeans when sitting, simple tailoring can fix that - as such, you’ll want to make sure you purchase jeans to fit your widest part aka, your hips. 

  4. Purchase your jackets to fit to your shoulders - everything else can be tailored around the shoulders. 

  5. While tailoring is a tool in the toolbox to help you, you’re better off returning something if it is very ill-fitting from the get-go. Sometimes you can’t tailor your way out of a bad garment - don’t try to fit a square peg in a round hole!

  6. You don’t need to tailor your sleeves if you have room to roll. If you’re okay with the appearance of rolling up your sleeves (which often looks flattering and more relaxed) then you can save yourself a trip to the tailor!

  7. When in doubt about your hemline, go longer. You can always take more up but as we know, it’s always difficult to add fabric once it’s gone. 

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