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 | 12.000+ Reviews5 out of 5 stars, 4.8/5 | 12.000+ 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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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(525 reviews)
5 ★
400
4 ★
100
3 ★
25
2 ★
0
1 ★
0
Sarah M. ✓ Verified
3/23/2026
★★★★★

Wasn't expecting much for the price honestly but the quality is so well done. Runs true to size for me.

Sarah M.
Julia L. ✓ Verified
3/18/2026
★★★★★

Received so many compliments. The fit doesn't cling and it photographs beautifully.

Julia L.
Isabelle H. ✓ Verified
3/10/2026
★★★★★

I'm obsessed with this. The material feels luxurious and it's universally flattering.

Isabelle H.
Rachel D. ✓ Verified
3/2/2026
★★★★

Cute and good quality overall. Fits a little different than expected but still lovely.

Rachel D.
Emily B. ✓ Verified
2/22/2026
★★★★★

Got this for my mum's birthday and she wore it the same day. Feels way more expensive than what she paid.

Emily B.
Margaret K. ✓ Verified
2/14/2026
★★★★★

Already own two other pieces from this store and this one might be my favorite. Solid stitching, no loose threads.

Margaret K.

COMBINE AND GET UP TO 25% EXTRA OFF

Built by Family. Passed Down Through Generations.

For over 30 years, The Bennett Family has believed in timeless style, exceptional quality, and craftsmanship that lasts.

As Thomas and Maggie prepare for retirement, their son James and his wife Emily are honored to continue the family legacy, carrying forward the same care, quality, and personal service that have defined our boutique from the very beginning.

Every piece is thoughtfully selected for its quality, timeless design, and lasting comfort, so it can be worn, loved, and enjoyed for years to come.

🤍 Thank you for being part of our family's story. Every order helps us carry this legacy into the next generation.

Loved By Our Customers

Patricia W.
★★★★★

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

Patricia W. – Seattle, WA

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 The Bennett Family provides reliable products.”

Sarah G. – Nantucket, MA

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. – Portland, ME

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, Bennett Family!”

Daisy C. – Savannah, GA

Evelyn L.
★★★★★

“Fantastic experience with The Bennett Family! 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. – Newport, RI

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 The Bennett Family provides reliable products.”

Karen G. – San Diego, CA

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 The Bennett Family!”

Judith C. – Charleston, SC