Girl in tan trench and cap outside a restaurant

Getting dressed on the weekend

Share

Date:
January 2, 2026

SEE ALL POSTS

Tips

filed in:

Author:
Madison Joslyn

Getting dressed on the weekend either brings emotions of excitement cause girl’s going out, or lassiez-faire because it’s the weekend and who’s leaving their couch? Whatever your feeling is, it’s something you have to do. Or maybe get to do. Unless you stay in your pjs and never change. You do you boo boo. But, if you decide you do want to get dressed (yay!) there’s something to be said for actually getting dressed on the weekend and throwing on a fit. Sweatpants allowed, don’t worry.

The weekend outfits

Getting dressed on the weekend in a weekend appropriate outfit looks different for everyone. Some of you are going out and need to be seen, others are running to the grocery store and want to be comfortable. Or maybe you’re sideline at the kid’s game and you don’t want to look like every other soccer mom. No hate to those mamas, just saying sometimes we want to look like our own person and not like we walked out of the basic catalog.

The combos

From full sweats looks (sweats and heels?) to partial sweats looks (are we even putting shoes on?) there’s going to be some moment during the weekend where you want to be comfortable. If you’re a part of the With Mads club you probably always want to be comfortable, even when you’re going out. So we’re going to focus on comfort for these outfit combos.

The combos ladies….

1. Cozy lounging at home

When you’re spending a low-key day at home with the kids or catching up on your favorite shows, comfort is key.

Outfit combo
Top: oversized knit sweater or a soft, cropped hoodie.
Bottoms: high-waisted leggings or joggers in a neutral tone.
Shoes: fuzzy slippers or slip-on sneakers for quick trips outside.
Extras: a cozy blanket scarf and minimal gold hoop earrings for an effortless touch.
What to think about: opt for fabrics that are soft and breathable, like cotton or cashmere blends. Stick to relaxed fits so you feel comfortable lounging but still put-together.

2. Sideline chic for soccer games

For those brisk mornings on the soccer field, layering is your best friend. You’ll want something functional yet stylish for cheering on your little one.

Outfit combo
Top: lightweight turtleneck under a quilted vest or puffer jacket.
Bottoms: straight-leg jeans or fleece-lined leggings.
Shoes: waterproof ankle boots or sneakers.
Extras: a crossbody bag, sunglasses, and a beanie.
What to think about: choose pieces that keep you warm without feeling bulky. Neutral tones with a pop of color (like your jacket or scarf) can keep the look fun and sporty.

3. Night out or evening events

Whether it’s date night or a social event, weekends are the perfect opportunity to dress up and feel your best.

Outfit combo
Top: satin camisole or fitted bodysuit with a blazer.
Bottoms: faux leather pants or a sleek midi skirt.
Shoes: strappy heels or pointed-toe boots.
Extras: statement jewelry, a clutch, and a bold lip.
What to think about: balance sleek and structured items like a blazer with softer textures like satin. Adding heels instantly elevates any outfit.

4. Brunch with friends

Brunch is a weekend staple, and it’s the perfect excuse to wear something fun and trendy.

Outfit combo
Top: flowy blouse or a fitted knit top.
Bottoms: wide-leg trousers or cropped flare jeans.
Shoes: loafers, mules, or platform sneakers.
Extras: a structured tote bag, layered necklaces, and cat-eye sunglasses.
What to think about: play with textures and patterns to make your brunch outfit pop. A hint of print or color adds personality while keeping the look daytime casual.

5. Weekend errands in style

Between grocery runs and picking up dry cleaning, your errands outfit can still be functional and fashionable.

Outfit combo
Top: long-sleeve ribbed tee or an oversized flannel.
Bottoms: high-rise mom jeans or utility pants.
Shoes: chunky sneakers or chelsea boots.
Extras: a baseball cap and a belt bag for hands-free convenience.
What to think about: prioritize easy-to-move-in pieces while adding small details (like a belt or accessories) to keep the outfit looking polished.

Whatever your weekend holds, the key is to mix practicality with style. These outfit ideas will help you look and feel great no matter what’s on your calendar.

Leave a Reply

Your email address will not be published. Required fields are marked *

MONTHLY RETAINER

PERSONAL SHOPPING

CLOSET CLEANOUT

WANT TO STYLE YOUR OWN CLOSET? BROWSE MY STYLING SERVICES!

Download Now

A GUIDE TO BUILDING YOUR FASHION FITNESS 

Learning how to identify your style, create formulas for daily outfits, and feel empowered by how you physically show up in the world is what you’ll gain from this free download. 

The Ultimate Fashion Strategy