How To Not Look Like a Frumpy Mom (fall/winter edition)

by | Tips, Hacks, & FAQ's, Wardrobe Wisdom & Style Tips | 0 comments

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Colder weather is on the way and us mamas need some inspiration for staying warm whether we’re out and about with the kids or keeping things running at home.

With the added layers of fall and winter, it can be a challenge to keep your mom outfit chic and straightforward. I always struggle with this more in the colder months. With that in mind, here are some basic rules of thumb to follow to avoid shabby when dressing for the fall or winter. 

Since I’m nearly ready to pop with our second baby, my gorgeous sis-in-law graciously agreed to be my model for this post! Doesn’t her smile just light up your screen?!

The spring/summer edition of these tips is now available! Click the image to read it in a new window.

For the fall/winter tips, keep reading below.

Here are simple guidelines for how not to dress frumpy this fall and winter.


Don’t: Wear a Loose Top with a Flowy Bottom

What’s wrong with the mom outfit below:

  • No shape due to both top and bottom being loose fitting.

  • No color contrast

  • Wrinkled (didn’t plan that! haha)


Do: Balance a Loose Top with a Fitted Bottom

What improved in the outfit below:

  • Swapped maxi for more fitted denim skirt paired with leggings to balance the loose sweater.

  • Added scarf or vest for color contrast and dimension.

  • The fashionable utility vest adds an on-trend look.

  • Kept boots, but now they add dimension to the outfit rather than hiding under the skirt.

  • Bonus Tip: Style your hair. Run a straightener through it to smooth out frizz or curl it with easy waves. It lifts your overall look! See how she has unstyled hair in the first pics and quickly curled in the next? It took her no more than five minutes to run the curling iron through it!


In addition to wearing fitted bottom with a loose top, it’s also OK to wear a flowy bottom with a fitted top. Basically: fitted with fitted or fitted with loose. Not loose with loose.

Ultimately though, take a look in the mirror and make sure the balance is working with your particular outfit. If something needs more shape, try adding a belt or a completer piece.

Add layers for dimension, such as leggings and boots, a scarf, or a vest/jacket.






For more winter fashion tips check out: How to Dress Warm & Cute in Winter


Don’t: Wear Sweat Pants/Running Shoes (Unless You’re Working Out)

This look is just fine if you’re working out or going on a hike with the family. But for day-to-day, it looks pretty shabby. If comfort is your goal, there are some casual alternatives that can lift your look!

What’s wrong with the outfits below:

  • (Left) The polka dot top is cute, but it clashes with the casual athliesure on the bottom.

  • (Right) Great for working out, not so great for going out.

Do: Wear Cute Casual Alternatives.

What improved in the mom outfit below:

  • Swapped running shoes and sweats for slip-on canvas shoes and jeans. Still comfy, but a better counterpart to the cute polka dot top.

  • Vest adds another layer of interest/dimension.

Of course, there will always be those days that you NEED to unwind in your favorite athletic wear, and you should feel the freedom to do that.

I love the idea given by one mom: she purposefully wears chic mom outfits for most days of the week but also purposefully saves 1-2 days of the week for wearing sweat pants. And you know what, when you only casual down like that occasionally rather than all the time, your family will probably find it relaxing too. It becomes a signal of “we’re relaxing today” instead of “just another day in the life of.”

To make this outfit warmer, simply roll down cuffed jeans, swap shoes for boots, and add a scarf and bomber jacket or peacoat. Can you picture it?

You might also like: Fall Fashion Trends That Are Mom-Friendly


Don’t: Wear Shapeless WORN-OUT Shirts or Pants.

What’s wrong with the outfit below:

  • While the top’s design is cute, it lacks shape. Paired with these worn-out jeans that also lack shape, the whole look lacks interest.

  • Adding a cardigan doesn’t help with shape.

Do: Add shape to your tops, only wear those that fit you right, and invest in a great pair of jeans.

What improved in the outfits below:

  • (Left) Addition of belt to shape shirt, a better fitting cardigan, and fitted, dark wash jeans!

  • (Center) Addition of belt to shape shirt, vest for color variation.

  • (Right) Using a plaid top and belt to add shape to the top. Also swapped sandals out for boots for a different look.


Layering with a button down shirt and belt or cardigan can redeem shirts that are ill-fitting. However, if you find that a shirt just doesn’t look your size no matter what you do with it, just get rid of it! Decluttering your closet of clothes that don’t flatter you will simplify the process of picking something to wear each morning.

Would it be helpful to have some casual outfit ideas for moms? 

Casual Outfit Ideas Wearing Burgundy Pants 
Casual Outfit Ideas Wearing Chambray 
Casual Outfit Ideas Wearing Leather Leggings



Don’t: Old or Baggy Jackets & Tees

Going out to grab groceries? That latest free t-shirt you got and workout hoodies are so often a go-to, but can be easily avoided with more stylish alternatives!

What’s wrong with this outfit:

  • Frumpy hoodie

  • Old tee

Honestly, my sis looks so adorable in anything that this really isn’t as bad as I was trying to portray! Basically, stay away from athletic jackets and free t-shirts unless you’re working on a project or exercising!

Do: Wear a Stylish Blouse and Fitted Cardigan, Vest, or Jacket.

What’s improved with this outfit:

  • A classic striped tee swapped out for old tee.

  • A fitted denim jacket adds shape.


If you opt for a cardigan, just make sure it’s the right length for your top (or dress if that’s what you’re wearing). It should either match a hemline, or fall far enough from it to look intentionally styled.

Bonus Tip!

You can also get comfy hoodies that are cute, feminine, and fit you well. Like this one that I ordered on Amazon recently.

See my full round up of cute hoodies and sweatshirts for under $25 on Amazon here.

Summary notes

  • Wearing something baggy or loose is not a problem as long as it is counterbalanced with something fitted in your mom outfit. For example, large olive green utility jackets are popular right now. To look right, you’ll want to wear them with skinny jeans, leggings, or a mini skirt + leggings.

  • If there are t-shirts in your drawers that you got for free, they are most likely going to bring down your outfits. They are not made to flatter you. Either get rid of them or reserve your favorite for down days, project days, and work outs.

  • Athletic pieces should be reserved for your most casual day(s) in the week rather than worn by default. To make this possible, it’s important to have casual alternatives that are just as comfortable. Keep this in mind when you’re making your shopping list.

I hope these tips help you keep it chic while you dress warmly this fall and winter season!

Do you sometimes struggle to avoid looking frumpy when you're choosing what to wear? The need for added layers in the fall and winter only makes it harder! Check out this mom bloggers 4 rules for dressing chic while staying comfy in the fall and winter. Click through for easy-to-follow examples. // How to Turn Frumpy Outfits Into Chic Mom OutfitsDo you sometimes struggle to avoid looking frumpy when you're choosing what to wear? The need for added layers in the fall and winter only makes it harder! Check out this mom bloggers 4 rules for dressing chic while staying comfy in the fall and winter. Click through for easy-to-follow examples. // How to Turn Frumpy Outfits Into Chic Mom Outfits