Wearbella – High Waisted Tailored Stretch Bermuda Shorts with Pockets
Wearbella – High Waisted Tailored Stretch Bermuda Shorts with Pockets
Wearbella – High Waisted Tailored Stretch Bermuda Shorts with Pockets
Wearbella – High Waisted Tailored Stretch Bermuda Shorts with Pockets
Wearbella – High Waisted Tailored Stretch Bermuda Shorts with Pockets
Wearbella – High Waisted Tailored Stretch Bermuda Shorts with Pockets
Wearbella – High Waisted Tailored Stretch Bermuda Shorts with Pockets
Wearbella – High Waisted Tailored Stretch Bermuda Shorts with Pockets
Wearbella – High Waisted Tailored Stretch Bermuda Shorts with Pockets
Wearbella – High Waisted Tailored Stretch Bermuda Shorts with Pockets
Wearbella – High Waisted Tailored Stretch Bermuda Shorts with Pockets
Wearbella – High Waisted Tailored Stretch Bermuda Shorts with Pockets
Wearbella – High Waisted Tailored Stretch Bermuda Shorts with Pockets
Wearbella – High Waisted Tailored Stretch Bermuda Shorts with Pockets
Wearbella – High Waisted Tailored Stretch Bermuda Shorts with Pockets
Wearbella – High Waisted Tailored Stretch Bermuda Shorts with Pockets
Wearbella – High Waisted Tailored Stretch Bermuda Shorts with Pockets
Wearbella – High Waisted Tailored Stretch Bermuda Shorts with Pockets
4.8/5 | Based on 2,975+ Reviews5 out of 5 stars, 4.8/5 | Based on 2,975+ Reviews

Wearbella – High Waisted Tailored Stretch Bermuda Shorts with Pockets

Regular price $169.00 Sale price$59.95 Save Today 65%
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Proudly serving customers since 1996.

Color
Size
Size Chart

Wearbella – High Waisted Tailored Stretch Bermuda Shorts with Pockets

Size Chart

If you're unsure which size to choose, we recommend selecting the larger size for a more comfortable fit.

SizeFits Waist (in)Fits Hips (in)Length (in)
S23.5–25.536–3815.5
M25.5–27.538–4016
L27.5–29.540–4216
XL29.5–31.542–4416.5
2XL31.5–34.544–4717
3XL34.5–3747–49.517.5

Only 5 left in stock

RETIREMENT SALE UPDATE: Due to high demand during our retirement sale, only a limited number of items remain. If you can still click "Add to Cart," it's still available.

Finally, shorts that look tailored and feel like leggings.

You've been choosing between comfort and looking pulled-together. Not anymore.

Wearbella brings you the high-waist tailored construction with super-stretch fabric — the polished look of dress shorts with the give of your favorite leggings.

They smooth your middle. They move with you.

Pull them on and go.

A summer favorite reordered in three colors.

✓ Look pulled-together in seconds
The tailored fly front and clean welt pocket give these shorts the look of dress shorts. No frumpy gym vibes. No effort.

✓ Stretches with you all day
Soft polyester-spandex blend moves when you move. Sit, drive, walk — no pinching, no riding up.

✓ Smooths your middle instantly
The high-rise waistband holds you in without squeezing. Flatters most body types from the second you pull them on.

✓ 2 pockets that actually hold your phone
Two real side pockets fit your phone, keys, and lip balm. No more bag for quick errands.

✓ One pair, seven ways to wear them
From morning coffee to dinner out. Pair with sneakers and a tank, or sandals and a silk top. 

What you get today

  • Wearbella shorts in your chosen color and size
  • High-waist tailored stretch construction
  • Two real side pockets + welt back pocket
  • Ready to wear out of the package
  • Free tracked shipping
  • 30-day at-home trial

Seasonal production run — once this color batch sells out, restock pricing may change.

Grab your color and size while this batch is still in stock.

30-day at-home trial
Try Wearbella at home for 30 days. If they don't fit, look right, or wear the way you expected, return them for a full refund.


Frequently asked questions

Do they ride up between the thighs?
No. The cut sits straight on the leg with enough room through the thigh to prevent bunching, even when you walk or sit for long periods.

Will the high waist roll down?
The waistband is wide and structured to stay flat against your stomach. It holds its shape through bending, sitting, and stretching.

Are they see-through?
No. The fabric is fully opaque in all colors, including the lighter neutrals.

Can I wear them for workouts?
Yes. The stretch and pockets make them great for walking, yoga, and light gym sessions — but they look polished enough for everyday wear too.

Specifications

  • Size: Available S–3XL (see size chart)
  • Material: Polyester
  • Lasts: Holds shape and stretch through hundreds of wears

How to wash

  • Machine wash cold with similar colors
  • Do not bleach
  • Hang dry to preserve stretch

We will always keep you updated about your order and make sure everything arrives safely. We offer free shipping in the USA on every order, and all parcels are securely delivered with UPS.

We offer a 100% money-back guarantee within 30 days of receiving your order.

Join 20,000+ happy customers
4.8(2,975+ reviews)
5 ★
400
4 ★
100
3 ★
25
2 ★
0
1 ★
0
Diane R. ✓ Verified
3/23/2026
★★★★★

The tailoring is impeccable, exactly what I hoped for. Fits true to size and feels like a real investment piece.

Diane R.
Karen T. ✓ Verified
3/18/2026
★★★★★

Ordered this for a weekend in Aspen and it did not disappoint. Compliments all night, fabric is gorgeous.

Karen T.
Margaret L. ✓ Verified
3/10/2026
★★★★★

I'm particular about quality at this price point and Caldwell Aspen exceeded my expectations. Beautifully made.

Margaret L.
Susan K. ✓ Verified
3/2/2026
★★★★

Fit is a touch different than I pictured but still a lovely piece. Would size up next time.

Susan K.
Patricia W. ✓ Verified
2/22/2026
★★★★★

Bought this for my sister's birthday and she wore it that same evening. Looks far more expensive than it is.

Patricia W.
Linda F. ✓ Verified
2/14/2026
★★★★★

This is my third order from Caldwell Aspen and every piece has been better than the last. Stitching and finish are flawless.

Linda F.

COMBINE AND GET UP TO 25% EXTRA OFF

A Legacy Worth Continuing

For more than 25 years, Caldwell Aspen has been part of our family.

My parents, Richard and Margaret, opened our boutique in 1998 with a simple belief: beautiful clothing should be chosen with care and loved beyond a single season.

A few years ago, they entrusted Caldwell Aspen to me. Today, I have the privilege of continuing what they started, personally selecting collections that stay true to the quality, elegance and care our customers have known for years.

In a world where small boutiques are becoming harder to find, every order truly matters to us.

🤍 When you choose Caldwell Aspen, you're not simply buying a piece you love. You're helping me carry my parents' legacy into its next chapter.

With love,
Elizabeth Caldwell

Elizabeth Caldwell outside the Caldwell Aspen storefront

Loved By Women Across The Country

★★★★★ 4.8/5 Based on 2,975+ Reviews
Patricia W.
★★★★★

“Fantastic experience! The order arrived quickly and safely, and the quality is top notch. I'll definitely be ordering again.”

Patricia W. – Denver, CO

Sarah G.
★★★★★

“My order was processed and delivered quickly, and I am extremely happy with the piece I received. The fit is perfect and the quality is great. It's good to know that Caldwell Aspen provides reliable products.”

Sarah G. – Portland, OR

Elizabeth S.
★★★★★

“Have ordered here several times now and each time has been an excellent experience. Products and service are truly high quality. A store you can trust.”

Elizabeth S. – Nashville, TN

Daisy C.
★★★★★

“I was hesitant to spend on a piece from a website I didn't know, but I'm so glad I did. The quality is amazing and the fit is perfect. Thank you, Caldwell Aspen!”

Daisy C. – Savannah, GA

Evelyn L.
★★★★★

“Fantastic experience with Caldwell Aspen! The order arrived quickly and safely, and the quality of the piece is top notch. A little exciting ordering online for the first time, but everything went exactly as expected. Will order again.”

Evelyn L. – Minneapolis, MN

Karen G.
★★★★★

“My order was processed and delivered quickly, and I am extremely happy with the piece I received. It's good to know that Caldwell Aspen provides reliable products.”

Karen G. – Phoenix, AZ

Michelle R.
★★★★★

“I could have hugged the delivery person. The packaging alone felt like a gift, and the piece inside was even better than I hoped.”

Michelle R. – Austin, TX

Diane P.
★★★★★

“Have ordered here several times now and each time has been an excellent experience. A store you can trust.”

Diane P. – Chicago, IL

Roberta N.
★★★★★

“I was hesitant to order from a website I didn't know, but I'm so glad I did. The quality is amazing and the fit is perfect.”

Roberta N. – Boston, MA

Judith C.
★★★★★

“I find online shopping difficult because I want it to be right the first time. But I ordered using the size chart and it fit perfectly. A big success at Caldwell Aspen!”

Judith C. – Sacramento, CA