33 Beautiful Downtown Boutiques for Local Fashion Finds

Simple icon of two tall buildings. Downtowns of Durham

From jersey knit tops to oh-so soft yoga pants, many of us have mastered the art of dressing comfortably during the stay-at-home phases over the last two years. If we’ve learned anything, it’s that comfort is key and “hard pants” are not the necessity we once thought they were. As we begin to re-emerge to our offices, visit with family, and enjoy other social gatherings, why not extend the comfort of casual into your wardrobe by investing in some fashion finds that pair comfort with style?! From wide-leg work pants to flowing blouses, and cute cashmere cardigans to soft dress shirts, it’s time to support local with a downtown shopping spree for comfortable fashion finds.

To help in your search for comfy attire, we’ve compiled this list of 33 downtown shops where you can free yourself from the restrictive world of your old wardrobe.

If you need more than a few pieces, you may want to head over to downtown Bowmanville and make a day of it. From designer digs to casual outfits and work scrubs, there are so many cute shops! And by so many, we mean you may want to bring a friend or two to help carry your finds. We simply couldn’t choose just one shop to feature, so here’s a list of all the must-visit vendors:

Gather store interior with clothing hanging on racks.
Gather, 51 King St. E., Bowmanville
Source: Gather

At the north end of the Town of Whitby you’ll find Humphrey’s Boutique, located in historic downtown Brooklin. Humphrey’s is the perfect place to find unique ladies upscale casual clothes, accessories and more. With attention to personalized service, they feature comfy high-waisted leggings, socially responsible clothing and accessories you won’t find in the average mall.

Buildings in downtown Brooklin.
Downtown Brooklin
Source: Durham Tourism

With an emerging group of designers and dress makers calling downtown Oshawa home, try locally-made athleisure at Frere Du Nord, upscale workwear at Krish Lynn Designs, or custom designed apparel at Joyce Hancock Designs. Looking for something fresh? Explore racks of vintage clothing at Baby’s Basement Vintage, and fun finds at Fashion Rebel. Doug Wilson’s Men’s Wear also offers upscale men’s wear, currently by appointment only.

Frere du Nord store interior.
Frere Du Nord – 45 Prince St., Oshawa
Source: Frere Du Nord

We simply can’t talk comfort without talking about bras. Why not treat yourself to a bra fitting at Comfort Bras by Pauline in the beautiful Pickering Nautical Village? Give them a call or visit their website before popping by to book an appointment.

Mannequins at Comfort Bras by Pauline.
Comfort Bras by Pauline, 611A Liverpool Rd., Pickering
Source: Comfort Bras by Pauline

Unlike a traditional thrift store that receives donations, Couture Consignments in Pickering Village lovingly hand picks every item on their racks. With an eye for quality and brand, this shop offers high-end designer labels on a budget—carrying women’s and men’s clothing, jewelry, shoes and purses.

Couture Consignments store exterior.
Couture Consignments, 82 Old Kingston Rd., Pickering Village
Source: Durham Tourism

Pulse, located in downtown Ajax, has an eclectic mix of both men’s and women’s clothing. From dresses to jackets and accessories, there’s a lot to choose from—especially on their sale racks.

Racks of clothing outside Pulse.
Pulse – 118 Harwood Ave. S., Ajax
Source: Durham Tourism

If you haven’t had a chance to shop in downtown Port Perry, you are missing out on a collection of shops and stores that will have you coming back for more! Find unique fashions and designer originals from Anja of Sweden, or pop by Kelly’s on Queen where everything is made in Canada. And, don’t forget to visit the historic sixth-generation Brock’s Department Store for endless fashion finds! There are so many great shops, you’re going to want to plan a patio visit for lunch to refuel for your awesome shopping adventure.

Kelly's on Queen exterior sign.
Kelly’s on Queen – 249 Queen St., Port Perry
Source: Kelly’s on Queen

While you’re in North Durham Region, swing by Maxine’s Fashions. Located in downtown Beaverton, is a great local go-to for fashion finds. From flowy dresses to relaxed collared boyfriend suit jackets and French dressing denim crop pants, there are lots of choices to up your style game while maximizing your comfort.

Maxine's storefront.
Maxine’s Fashions, 360 Simcoe St, Beaverton
Source: Maxine’s Fashions

The Thrift Hub in quaint Cannington is a great spot for finding thrifty fashion finds. From clothes to housewares, furniture and books, there is lots to find during your thrifting adventure.

Thrift Hub sign on exterior building.
The Thrift Hub, 33 Cameron St. E., Cannington
Source: Durham Tourism

Woods Clothing in gorgeous downtown Uxbridge has everything you need to build back your comfy work wardrobe. With lush kimonos, cute cardigans and on-point pants, you can create the look you want that’s not just stylish, but also a joy to wear!

Clothing displayed on mannequin at entrance of Woods Clothing.
Woods Clothing, 70 Brock St. W., Uxbridge
Source: Woods Clothing

Delightful downtown Whitby has all the back-to-work items you could ever need—from beautiful tops and stylish dresses from Turquoise to high-end fashion pieces from Jayne and upscale consignment items from Inspired By You. This is one spot where you’ll be sure to find something to make your wardrobe sparkle.

Jayne store interior with clothing hanging on racks.
Jayne – 103-B Dundas St. W., Whitby
Source: Jayne

While shopping in our downtowns, don’t forget to treat yourself to a bite at a local restaurant! Be sure to explore our website for more great shopping in Durham’s downtowns.


NOTE: At the time of publishing, Durham Region and the Province of Ontario are in Step 3 of the Roadmap to Reopen; the Province’s three-step plan to safely and gradually lift public health measures, based on ongoing progress of province-wide vaccination rates, and improvements of key public health and health care indicators. Many businesses now require proof of vaccination; please check ahead for specific business policies. Residents are encouraged to follow health guidance when safely exploring their local communities, including wash hands frequently, wear a mask and physically distance from others.