Finessing Fit: 10 Practical Principles For Choosing Clothes That Fit and Flatter

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I had so much fun putting together my 11 Strategic Style Solutions Guide! While it only skims the surface, it’s packed with timeless principles and useful information for you. I am confident you can implement what you learn right away but boy, oh boy, there’s so much more to talk about!

This first blog series is dedicated to teaching you more about each of the Style Solutions outlined in my guide. (If you don’t have your free copy, join the mailing list and check your inbox. It’s my gift to you.) 

First up: all things fit.

10 principles for choosing clothes that fit

Did it surprise you that the cornerstone of great style is fit? I love this principle because everyone⁠—and I mean everyone⁠—can learn how to be really picky around how things fit. Here are a few things to keep in mind as you explore your closet and shop for new garments. 

1. Ignore numbers

You need to get to the place where the size noted on garments doesn’t trip you up. It is inconsequential to style. Brands vary. International labels vary. The designer’s model sizes vary. Refuse to let a number define you. Your value is not a label and great style is not about a size.

2. Dress accordingly when you shop

When you head out to shop for a specific garment, you need to think ahead and be prepared. 

For instance, if you’re in the market for a new winter coat, be sure to wear a blazer or have a bulky sweater with you so you can ensure the coat will fit comfortably over those pieces.

If you plan on trying on dresses for a special occasion, bring along the appropriate underwear and shoes in a tote bag so you can evaluate the dress more accurately. Better to get it right in the store and save yourself a trip.

3. Make sure you can move

Style, comfort, and ease are all wrapped up together. In order to look and feel your best, clothes should skim your body but not restrict movement.

If you’re trying on jackets and coats (or anything with sleeves for that matter,) cross your arms across the front of your body. Is it easy to do? If you’re shopping for pants or a skirt, stand and sit. Is the waistband comfortable? Can you bend over to slip on your shoe? Do whatever is necessary to ensure that whatever you’re trying on moves with you.

4. Watch for shoulder lines

Particularly with jackets and coats, if the shoulder seams do not sit squarely at the edge of your shoulder, move on.

If the shoulders are too narrow, the sleeves won’t fall properly, the buttons won’t fasten without strain and the back may pucker. You’ll look visibly larger. Not a good idea.

Conversely, if the shoulder line droops over your shoulder, you’ll look droopy too. Shoulders are intended to give structure, particularly to jackets and coats, so the shoulder pads inserted by manufacturers can do wonders to improve a sloping shoulder and create a beautiful, strong line. Get really picky about this. You’ll be glad you did.

5. Be smart about buttons

I don’t recommend purchasing a jacket or blouse if you can’t comfortably do up the buttons.

Some people justify purchasing ill-fitting jackets on the premise that they'll just wear them unbuttoned. This isn't wise. That doesn’t mean you can’t wear one unbuttoned; the jacket just needs to fasten comfortably so it can function properly. A rule of thumb is that you should be able to place three fingers (side by side) between your ribcage and the buttoned jacket.

In terms of blouses, make sure there's no pulling across the front. Button placement is a critical detail. If the buttons aren't sitting properly, your blouse might gape open. No one needs to spy inside your top so either select another blouse or fall back on fashion tape. This one's my favourite.

6. Examine sleeves

What sleeve length is correct when purchasing coats and jackets?  Excellent question!

You have two prominent bones at the end of your arm: one on the outside of your wrist and another at the other side at the very end of your thumb. Ideally, sleeves should fall between the two. 

It’s a personal choice, really. I prefer mine to rest right at that wrist bone; you might like yours a bit longer. Either way, just make sure sleeves are neither too short nor too long (unless you plan on making alterations.) This is an important detail so make sure you get it right.

7. Know your hemlines

The length of your skirt will depend on a couple of things. First, your overall shape and size. Second, the shape and style of the skirt. We will unpack this more in another blog post. For now, here is a truth you can take to the bank. You never want a hemline to land at the fullest part of your leg. Never. Skirts, dresses, capris or shorts⁠—you name it.

As for pants, you want a cropped style to be hemmed to just above the ankle bone. A dress pant should have a bit of a break at the ankle and rest ½” below the top of your shoe.

8. Pay attention to pockets

When it comes to pants, everyone loves a place to store their hands (or phones!) but pockets can present problems.

If you are full through the hip and thigh, side pockets (slit or slash) can sometimes pooch out, cause a visual imbalance, and draw attention to a part of your body you’d rather not shine a light on. I suggest having those kinds of pockets sewn shut. An even better solution is purchasing pants without waistbands, with a side zipper and no pockets at all. They are sleek, clean and smooth.

9. Consider alterations

A good tailor is a surefire way to achieve a top-notch fit. It’s rare that a garment can be purchased off the rack and not require some kind of adjustment in order to fit just so. Don’t pass on something just because it’s a bit too big. Consider what a tailor could do.

The investment is almost always worthwhile. Taking in waistbands and hemming pants or skirts is no big deal. Adding a few darts to give something shape is relatively simple. 

That said, some alterations are very involved. Adjusting major structural components like the placement of a shoulder seam is much more complicated and costly. It’s important to consider the investment before you purchase a garment that isn’t quite right. (And as a quick aside, if you’re tempted to buy a jacket that doesn’t fall properly on your shoulders, unless it’s a screaming deal, pass on it. Trust me. Nine times out of ten, it’s the best decision.)

10. Notice how you feel

As you are out shopping, I want you to be keenly tuned in to how things make you feel. This is crucial. Do you feel like yourself? Do you like the reflection you see in the mirror? If the answer is no, walk away. No amount of alterations will compensate for feeling comfortable in your own skin.

Beyond that, how does the garment itself feel? Does the fabric appeal to you? Does it feel good against your skin? Can you move with ease? Does the garment follow the natural line of your body and rest nicely on your shoulders? Does the jacket have a soft, supple lining that caresses your skin every time you pull it on? Do the pants skim your body and make you feel like a million bucks?

How you feel is exponentially more important than how you look.


Great style, the kind that appears effortless and easy, takes time.  Isn’t that the way it is with everything? When something looks easy it’s typically because, behind the scenes, there has been lots and lots of practice.

Understanding how to discern the right fit will serve you in so many ways. You'll make educated decisions, avoid costly dead-end purchases, and develop a wardrobe you love to wear.

Like any good coach, I’m committed to seeing you excel. I’m here to answer your questions, respond to your issues and cheer you on. Drop a comment below. I’m standing by. See you next week!