Style Q&A: How to Layer With Wide Leg Pants, Dresses for Pear-Shaped Women, and More

putting me together + style questions and answers

I always say style should serve your life, not stress you out. That’s why every month inside the PMT Style Club, we host live style Q&A calls where members can get practical help, friendly advice, and real solutions to their style struggles. Members can ask whatever style questions they’re stuck on and get real, practical, personalized answers they can actually use.

In case you have some similar questions, I’m taking you behind the scenes and sharing some of our style Q&A from the last couple of months of our calls along with easy style tips you can steal. Let’s get to it!


Q: How can I bring to life a creative/modern style that feels “me,” but still works with my hourglass shape?

Nellie shared that she loves offbeat shapes and colors, but if she’s not careful, her outfits can look a little chaotic. Her Pinterest board is full of slouchy, modern silhouettes that she felt aren’t always flattering on her hourglass figure.

This is a great question as it can be hard to imagine how to actualize the look you want with the shape you have. Here’s a peek at her board:

putting me together + style q & a

We encouraged Nellie with a few things:

Focus on the vibe, not the exact silhouette.
Look for details like interesting colors, unique textures, or playful elements — but in cuts that fit and flatter your shape better. You don’t have to replicate the exact baggy fit to capture the spirit!

You can pull off more silhouettes than you think, but look for the nuances in the fit points and proportions of the items.
For example, I’ve talked about how a lot of women think they can’t pull off wide leg jeans without feeling shapeless or looking sloppy, but almost everyone can look great in them without looking shapeless. However, some of us need to look for specific details about how they fit at the hips and thighs in order to pull that off. (I lay it all out for you in great detail HERE.)

So, maybe Nellie won’t wear those EXACT pants that she sees on someone else. But she can wear pants in a similar color, even in the same cut, but a different pair that hits the nuanced notes of fit better on her.

“You don’t owe flattering to anyone.”
Most importantly, Courtney, our PMT stylist and Community Manager inside the Style Club, also dropped this gem that you don’t owe flattering to anyone. Courtney and I are both firm believers that you don’t HAVE TO wear clothes that are flattering. We want you to wear what makes you feel good. If things that are flattering make you feel good, we give you the tools to do that. If you don’t give a rip about that, we empower you in that, too!

It’s all in the details.
We then broke down a few of the outfits on Nellie’s board and some of her own outfits she shared in our private Facebook group and offered simple tweaks that helped her outfits still feel creative but a little more polished — without losing the fun! For her, because she has a very creative/modern vibe, one big tip was that we even want her basics to have a little extra detail. So, jeans with an interesting detail at the hem or a semi-funky silhouette, for example. Extra details, even in standard wardrobe essentials, will give all of her outfits that oomph that she craves.


Q: Suggestions for dresses for pear-shaped women?

Jennifer asked for help finding dresses and skirts that flatter her pear-shaped figure, specifically that don’t make her hips look wider.

Additionally, I know what Jennifer’s Style Type Mix is, what her color palette is, and what her height is, so I kept all of that in mind when searching for dresses for her.* She also didn’t want midi lengths because they overwhelm her and hit her at undesirable spots.

*Didn’t know that we can help you personally shop in the Style Club? Yes, we love helping you save time! Like I said, members can ask anything, and we’re here to help, including shopping help!

Here are a few options I pulled for her:

1. Draper James Dress (update: no longer available): This dress is cute and totally in her colors and style! It cinches at the waist to define her narrow waist and can flow over wider hips.

2. Anrabess Dress: This is a comfy t-shirt dress with extra details that elevate it. You can dress it up or down, easily pairing it with wedges, sandals, and lifestyle sneakers. The waistband again helps define her shape while the a-line skirt portion will flow over hips. The extended sleeves at the shoulders helps fill in narrower shoulders that pear shapes tend to have, which balances out wider hips. (Again, like I said with Nellie’s question above, you don’t have to wear things that are flattering, but I know Jennifer likes to!)

3. Denim Skirt (update: no longer available): This shape is nice for pear shapes, as it falls straight down from the hips to balance them out.

Then, as a follow-up, a couple of members also shared these dresses for Jennifer:

4. Banana Republic Factory Linen Dress

5. Old Navy Shirt Dress: Jess, one of our rockstar members who shared this, recommended belting it for more definition. CUTE!


Q: How do you layer with wide leg pants without looking like a box — especially if you’re pear-shaped?

Erica asked for help figuring out how to layer outfits with wide leg pants — without feeling like she lost all her shape.

Here’s what we worked through together:

  • Make sure the pants fit in a way that still hugs your shape.
    A good fit at the waist and hips makes a huge difference in defining your shape underneath the wider leg. (For all the details, read my post How to Look Good in Wide Leg Jeans: Four Fit Tips to Find the Right Pair!)
  • Pick shorter layers.
    Jackets, sweaters, or cardigans that hit right at the top of the hip help balance proportions naturally.
  • Tucking your shirt is an option, but not a must.
    A full tuck can give even more definition, but you can absolutely skip it and still look pulled together.

To help Erica really see it, I pulled up outfit examples from our Community Manager and stylist Courtney who has a similar build and rocks wide leg jeans regularly. Courtney’s pictures are below. Note where all of Courtney’s layers hit and how she doesn’t look completely shapeless, even without tucking any shirts (she’s a staunch anti-tucker 😂), thanks to jeans that fit at the hips and layers that sit right on top of her hips.

putting me together + style q & a + black wide leg jeans + black and white striped shirt + denim jacket + mary jane flats + tan cardigan + white tee + light wash wide leg jeans + white sneakers + white and tan and blue floral cardigan + tan tee + flare jeans

Q: How do you actually find time to work on your style when life is so busy?

Leslie shared that even though style is super important to her, it just wasn’t getting prioritized with everything else going on.

A couple of members shared their rhythms, such as doing a little bit each evening or sometimes binging on various lessons inside the Style Club if they’re in a heavy learning season. Then, we also came up with some ideas:

Use the time you’re already showing up.
Since Leslie was consistently joining live calls (go Leslie! 🙌🏼), I encouraged her to use that time to actively work on style tasks. I told her I WANT her multitasking, using the live calls as accountability time to actually DO style stuff, not just keep listening, reading, or learning — like ordering the jeans she’d been meaning to grab for weeks.

Focus on one next step at a time.
We agreed that each call, I’d help Leslie figure out her next action step so that she can keep making progress, whether that’s finding jeans, ordering dressy shoes, or adding versatile everyday sneakers to avoid defaulting to slippers.

Curious as to what her first steps were? Leslie’s steps:

Leslie’s very first step was to get her color analysis done. She shared months prior that color was the biggest thing for her in feeling good, but she felt very stuck without having clarity on her colors. I told her that that was her very first step, and she did it while we were on the call!

Next was to order jeans she’d been meaning to order. She finally did it, and now she has not one, but a couple of pairs of jeans!

Her next one was to get a pair of versatile dressy shoes, since she wanted to have options for going out to dinner. She hadn’t yet done that, but she did realize that in her daily casual outfits, she usually defaults to slippers, which ruins her outfits. I said I want her to have one pair of versatile lifestyle sneakers and a pair of sandals that go with everything so that she CAN just throw something on and run out the door, but actually look pulled together. I had members share their favorite lifestyle sneakers and sandals for Leslie, and she ordered sandals right on the call!

It’s been so fun to see Leslie’s style grow little by little — all from taking small, doable steps instead of feeling like she has to overhaul everything at once.

If you want to make progress with your style, here’s what you can do:
1. Use time you’re already showing up somewhere to work on style
2. Put it in your schedule if you need to
3. Determine each of your next steps, one small thing each time. If you’re not sure what to do, start with my free Starter Kit Wardrobe Guide. Make sure you have each of the pieces on the list. If you don’t, make each missing piece your next set of to do’s!

And of course, if you could use a little oomph, motivation, and coaching from me like we’ve been coaching Leslie, join us inside the Style Club so you can make progress and feel great in your clothes the way you desire to!


Q: Should I get red espadrilles or red or pink Mary Jane Rothy’s?

Amanda was debating between two shoe options and wasn’t sure which would fit her style and wardrobe better.

We walked through a few things to help her decide:

  • Red espadrilles felt like the better match because their two-toned look (woven bottom + red top) makes them easier to dress up and dress down — perfect for more casual outfits, too.
  • The Mary Jane Rothy’s, while super cute, would feel a little too dressy for some of Amanda’s everyday looks.

To help Amanda visualize it, I pulled up a few of her outfits she had shared in our private Facebook group and showed how the espadrilles would totally work whereas the Mary Janes might feel out of place. Our rockstar member Jess shared she has the Rothy’s and pretty much only wears them for dressing up to teach.

Here’s a tip for whenever you’re trying to decide between pieces:
👉🏼 Think about your last 3–5 real-life outfits that you’d want to wear with the piece.
👉🏼 Picture wearing the new item with them.
👉🏼 Choose the option that fits more of those outfits!

(I can’t wait to see Amanda rock the espadrilles!)


Those are the questions for today, and perhaps I’ll share a few more soon.

Sometimes it just takes a tiny tweak (like a shorter layer or a new pair of shoes) to completely shift how you feel in your clothes. And sometimes it helps to have a group of people in your corner who can see things you might not — and cheer you on while you try something new.

If you’ve ever wondered some of these same things, I hope this gave you a few helpful answers to get going!

And, if you want the kind of support and insight we shared in this post — and a style coach who’s cheering you on and helping you take the guesswork out of it — come hang with us in the PMT Style Club. We’d LOVE to help you feel confident and proud each day!


PMT Style Club

Hey there! If you love playing with new styles and want to be around other style enthusiasts, join us inside the PMT Style Club! In it, we have fun honing our style, experimenting with new things, and learning from experts, like color specialists, petite experts, plus size experts, and more. We also have monthly style challenges to keep things fresh and make it FUN to get dressed! Check out how the PMT Style Club can help you and join to get access to all the resources and the amazing style community, HERE!

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