Personal Coaching on How to Choose a Dress Style

Learning how to choose a dress can be key to creating a simple wardrobe and style uniform.


As someone who wears almost exclusively dresses, I know what an amazing freedom this choice can offer in your wardrobe for simplicity and ease of putting on ONE item. But choosing the right dress can get tricky. 

So many silhouettes, not to mention the details like sleeves, necklines, colors, and prints, and it can feel overwhelming to find the right one for you. Join me with Style Star Becki to discuss finding her perfect dress silhouette. 

Although she knows so much about her own style, and has many personal uniforms nailed down, the right dress has been eluding her. In this episode, we talk about some options she has and find the little details that make her perfect dress style.

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Stacey: We’re here this morning with Becky Zingg, our star for September. Before we get started, why don’t you tell everybody in the group how you earn these 15 minutes with me?

Becky: By just doing what I always do: posting, liking, and commenting. This is my favorite place to engage. 

Stacey: Yep, that’s how you win the 15 minutes. Every month we have a style star. To win, you need to be the person with the top engagement, and that includes comments, posts, and likes. Facebook tells me who it is every month. Just be active in the group and it could be you next month! 

It gives you a chance to ask your burning questions and get my help. One-on-one for free. Having said that, Becky you’ve been with me a long time. I think that you might’ve been one of the first people to join my Facebook group when I started. 

I know that you’ve learned so much and your style is pretty cemented at this point. So what questions do you have for me today?

Becky: I feel like I have not yet found an ideal dress silhouette. Part of the challenge is that I cannot make dresses that aren’t petite work for multiple reasons. One is that I have a short torso. That takes out of the running a lot of companies that just don’t even make petite dresses.

How to Choose a Dress: Colors and Essences

Stacey: As a fellow tiny person, I understand this problem. As somebody who wears dresses every day, I do understand that finding the silhouette can be difficult because they’re all so different. So for everybody, Becky sent me seven pictures of herself in one dress she’s thinking about buying. I’m going to go through and analyze them.

Stacey: The first I can see are some trends in essence and I can see some trends in the things that I know that you like to wear. If I had to take a quick stab without really thinking too much about it, my first thoughts were that classic is your primary. 

I say that because of the way you like jackets, styling, tailoring, and some of that structure in your clothing. You’ve probably got gamine and ingenue mixed in there as well.

When I look at your color palette it’s pretty cohesive and I feel like yours isn’t super large. This is a perfect example of the way classic essences use color because they tend to stick to neutrals with just a few classic colors, like cobalt blue or red. 

You have a wine dress, some red here and there, and then you have some seasonal pops, like the lighter coral color that you use. Of course, there’s navy, black, and white in there. You wear cornflower and cobalt and you wear red a lot. 

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How to Choose a Dress: Silhouettes

You wanted to talk about silhouettes after I rambled for a few minutes. What I see interestingly enough is a lot of consistency in the silhouette. I see that you’re going for a fit and flare for some waist definition in most of the dresses.

Except this dress is not petite. I can tell it’s not petite because of the way the waistband is curving down. My suggestion when I saw this dress, because I think you like this dress other than the fit, is to take it to a tailor and have them pull the waistband up.

Becky: I already had someone take it in at the zipper at the back and it brought it up a little bit, but not enough without doing some major work because there are pleats and puffs. 

Stacey: Yeah, I mean, honestly, is this a sheared waistband?

Becky: It’s gathered underneath. 

Stacey: I would almost say even just cinch the waist just a little bit and see if that pulls that up just a little bit. That might be better. The other interesting thing I see is that you tend to go with tiered skirts.

Becky: 1, 2, 3 of them. Oh my goodness!

Stacey: This is a really interesting feature. Tiered skirts have been really trendy here lately. They kind of lean into that boho natural vibe just a little bit. You could maybe say they’re sort of ingenue, but I get a lot of boho vibes from it. 

Becky: It’s the only boho outfit I have in my piece in my whole wardrobe. 

Stacey: It’s interesting because, from that perspective, those prairie dresses have been trending. I’m getting it from this. The gingham is the only thing that’s making it not a very prairie dress. This one with the light color, I’m getting it here. 

I want to talk about my favorite one. I know that this one has caused some issues with how you feel in it and the fit. What I love about it is that it gives off a vintagey kind of vibe when you put everything together. 

It’s very much like a fitted bodice with a fuller skirt, like a housewife from the fifties.  I love this one and think that it taps into that classic essence because it harkens back to that vintage dress style. It also has the fun of the polka dots and your colors. 

It’s marrying some of the best things that you enjoy. I love this keyhole neckline and the sleeves, which have a little bit of that puff sleeve to them. Honestly, when I look at all these pictures together and I think about this one it’s leaning a little romantic. I feel like going with more of a vintage cut is going to be most flattering for you.

Becky: Do you know, my issue with this one is I feel really busty in it.  Because I’m short-waisted, I feel like it goes, oh, bosom. That’s the one thing about this that makes me kind of go, nah.

Stacey: It’s interesting because I understand why it feels that way as a fellow busty person. But it doesn’t come across me that way. Of course, if it’s feeling that way, you could always try minimizer bras, which will give you some squish.

Becky: I have a minimizer on in this picture.

Stacey: Checkmark. I did that. It may be the dart placement because it’s right down the middle of your bust and also coming up across your bust.  Darts that start center and then go down below might just be a little bit better for you also. 

These dresses also could work because they’re typically in a stiffer fabric, not a knit. They’re usually in a woven fabric with darts across the back as well. So it may just be an issue of choosing dart placement. I don’t love this one for you.

Becky: Which one is that one?

Stacey: The one you were thinking about buying.

Becky: It’s not the color I would order.  Not even the cut or anything.

Stacey: I’m not sure. It would be interesting to see you try it because a wrap dress is sort of classic, but it’s a knit, right? You don’t wear a lot of knits. Everything here is woven pretty much. There’s something else, all that strong classic essence needs the structure of the fabric.

How to Choose a Dress: Custom Dresses and Alterations

Becky: Okay, so let me ask you a question because I have somebody who could make dresses for me. If we were picking the burgundy dress in the top corner, can I cherry-pick all my favorite parts and have somebody make a custom dress? I feel fabulous in that, but I do not like the neckline where it’s at.

Stacey:  If we were going to do that, I do love the neckline on the blue dress.  This would be your signature neckline for dresses because it wraps and curves. Roundness is a feature of some of that softness which helps to balance the stiffness of the classic with some of your softness too. 

I love the neckline. I would talk to her about dart placement and how this makes you feel busty and try to find some ways around that for sure. I do like the skirt on this one, but it’s the deep V and the coloring together that kind of pulls it off a little bit. 

I suggest you have her mock up one version for you so that you can get it right before she starts making you a whole bunch. That also allows you to pull the patterns that you want, the colors that you want, and the fabrics that you want. 

Becky: So if you were going to ditch one which would you choose?  I wear the navy dress a lot in the winter because I just don’t have a lot of winter dresses. That one doesn’t have a whole lot of shape. Would that be the one you’d ditch?

Stacey: Is there a waist seam here?

Becky: I do have a waist, sort of.

Stacey: Is there a seam here though on this dress? 

Becky: Yes. There’s a seam and the top fabric is a different material than the bottom. 

Stacey: This is the next one where I would say to have the waist altered just a tiny bit. I can see that it’s sagging here, which means there’s a bit of a fit issue. I feel like if you had it altered a little bit, it would fit better and look better. 

Sometimes that’s really the trick. If you think about fashion construction and fashion production, it’s made big box for standard body sizes. Once upon a time, that’s not how clothing was made. It was made for your body. Even when they first started bringing out made-to-wear kind of clothing, people would buy it and alter it at home or take it to someone and have it altered. 

A lot of times all you need to do to save a garment, to save a piece of clothing that you overall kind of like, is just some small alterations. There are some alterations that I’ll tell you are not worth the money or the time. 

Things like shoulders, you don’t want to go there. But something like a nipping in a waist is a pretty small alteration. And fairly inexpensive as well. That will make a big difference in how something like this looks.

Becky: Okay. And the other dress that’s not petite. I have two of them, that gingham one in the bottom corner. I’d have to take it up at the shoulders because there’s too much fabric in between my shoulder and where the waist is. 

Stacey: I don’t love this one. The length is a little bit wrong. It needs to be a little bit shorter or just go all the way down. It is a strange length because you didn’t buy a petite. When you’re a tiny or smaller person it is hard because everything is shortened in different ways. I don’t want to tell you to get rid of stuff because I don’t hate it. It’s just not the best for you. 

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No more wondering how to choose a dress, these tips will help you find the perfect dress style.

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