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Style Guide

How to Choose the Perfect Crossbody Bag for Your Lifestyle

Leah Mickschl ·Founder, Pretty Simple · ·6 min read

Walk into any boutique, or scroll through any fashion site, and you'll find dozens of crossbody bags. Different sizes. Different shapes. Different price points. It's a lot. But the right crossbody doesn't just look good in photos; it works for your actual life, the one with school drop-offs, grocery runs, date nights, and everything in between.


Why Crossbody Bags Have Dominated Women's Accessories for a Decade

The crossbody bag has quietly become the most versatile piece in women's fashion. Practical enough for the school pickup line, dressed-up enough for date night, and hands-free for everything in between. When you spend enough years living your life with a bag on your body, you learn what actually matters, and what's just marketing.

Here's the framework I use when I'm designing our bags, and it's the same one I'd use if I were shopping for one.

Diagonal Woven Westlyn Bum Bag

Step 1: Get the Size Right First

Before you fall in love with a color, decide what your bag actually needs to hold. Phone, keys, wallet, sunglasses? A slim crossbody works beautifully. Add a water bottle, notebook, or diapers into the mix, and you need something more structured with real capacity.

The mistake most women make: buying a bag that looks perfect in the mirror but can't hold what they actually carry. Measure your essentials, then measure the bag interior. The math should work.

Reader Favorite

Westlyn Woven Bum Bag

Our top-selling crossbody, available in 32+ colors. Fits phone, wallet, sunglasses, and keys without bulk, the everyday bag customers keep coming back for.

Shop Westlyn, $72

Step 2: Match the Strap to Your Body

Strap length is the difference between a bag that looks proportioned on you and one that fights you all day. Shorter women (5'4" and under) generally look best with straps that hit at the hip. Taller women have more flexibility to wear the bag higher or lower as a style choice.

Adjustable straps are worth prioritizing, they let you switch between shoulder-only and crossbody, or shorten the length as you layer with heavier winter coats.

Step 3: Think About Closure and Security

Zip closures keep contents secure, ideal for travel, commuting, or anywhere you're in a crowd. Flap-and-snap closures are faster to access but offer less security. Our Quilted Travel Collection prioritizes zip-top closures specifically for this reason.

For everyday use where quick access matters more than maximum security, a magnetic snap or turn-lock keeps things accessible without slowing you down.

Diagonal Woven Westlyn Bum Bag
Diagonal Woven Westlyn Bum Bag

Step 4: Match the Bag to the Occasion

Not every crossbody needs to be a workhorse. If your everyday bag is a woven bum bag for errands and school runs, a small dressier crossbody for date nights or dinners with friends is worth having as a second piece. Different materials, different vibes, different jobs.

This is one reason we design so many silhouettes in the 3 Sisters Collection, each bag has a job.

Step 5: Choose a Material That Fits Your Life

If you're outdoors a lot, kids in the mix, or unpredictable weather is standard, choose a material that can take a wipe-down. Woven vegan leather, PU-coated canvas, and nylon are all forgiving.

For structured, refined looks, think blazer-and-jeans territory, smooth vegan leather in a neutral tone reads elevated without being fussy.

Our Most-Loved Crossbodies Right Now

  • Westlyn Woven Bum Bag, the top seller, hands down. 32+ colors, fits everyday essentials.
  • Sienna Slouchy Woven Shoulder Bag, for the everyday minimalist. Slightly larger, still crossbody-strapped.
  • Wrenlee Woven Flap Crossbody, more structured, refined finish. Good for date night.
  • Pebbled Sabrina Studded Bum Bag, the original 3 Sisters silhouette. A brand favorite.

Whatever you choose, buy the bag for the life you actually live, not the one you post on Instagram. The bag that gets used every day is the one that pays for itself a hundred times over.

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