Women’s Dressy Sneaker Outfits For Any Age

I’ve been a professional stylist longer than they’ve been alive, but I’m totally taking style notes from Gen Z so that I can source women’s dressy sneaker outfits that look cool at any age. I love people-watching and outfit-stalking. I know every woman wants to look effortlessly stylish wherever we go and I’m convinced women’s dressy sneakers are the easiest way to do that. I’m running out of room in my closet but I can’t stop buying sneakers so I’ve decided to make more casual and dressy outfits to go with them. Here are a few you can copy.

Women’s Dressy Sneakers & Dresses For Any Occasion

I can’t get enough of this outfit combination. It seems to work for any occasion.

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The Best Women’s Dressy Sneakers For Travel

Sneakers are the best shoes to travel with all year long. These are the the styles and brands I recommend the most.

1. Classic Converse

There is just something utterly cool about Converse sneakers. They are ageless and effortlessly complete any outfit.

2. Leather Sneakers

A leather sneaker is more supportive and can be worn all year long. Bright white is classic and easy to dress up. Shop my top 6 women’s white fashion sneakers in THIS POST.

I highly recommend P448 or Paul Green. They are quality-made in Europe and designed for lots of walking.

Jennifer Sattler Sacramento Doco Center wearing metallic joggers Adidas sneakers and silver chanel purse white cdc bracelet
Adidas Sneakers | Joggers Similar | Black Turtleneck | Vintage Chanel from Panache

3. Adidas

Everyone I know is obsessed with these sneakers. My husband and I even have matching pairs. They are so comfortable and I love the stripes on the side.

4. Retro Sneakers

These are the most fashionable sneakers right now. Balance this bulkier style with an almond-shaped toe and by showing a little skin around your ankle.

Jen wearing rag and bone retro runner sneakers at pink door holding the tote bag and wearing a yankees baseball hat
Rag & Bone Retro Runner

If you wear a lot of dark colors on the bottom or want a style that doesn’t stick out in the winter I recommend a darker color.

Designer Inspired Sneakers


Dolce Vita

Alexander Wang

Steve Madden

The Best Summer Jeans With Dressy Sneakers

The best jeans with dressy sneakers this summer are those that stop right around the top of your ankle bone.

The most flattering jeans with sneakers are those with a straight leg shape. If you want to wear a flare or wide leg jean with sneakers try platforms for more height or a low profile fitted hightop sneaker that connects tucks under your cropped jeans.