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A dress—is there anything better? You grab it from your closet, no thought required, and you’ve got an automatic outfit. Even without accessories, you still look stylish, pulled together, and intentional—with only one article of clothing. Dresses have long been worn for upscale occasions, but casual, cotton, midi, oversized dresses are now so popular that they literally can be worn every day. I wear the latter with a pair of white sneakers to the playground with my littles, but can easily sub in a snazzy pair of flats to take the same casual dress out to dinner. There’s truly no place a dress can’t go. With this in mind, we’ve rounded up where to buy quality, chic, and reasonably affordable dresses.

Boden (Sale Section)

If I could only recommend one place for dresses, it would hands-down be Boden. I don’t know how, but Boden has managed to create an equally timeless, well-made, showstopping, flattering and stylish dress time and time again. There’s a reason that I’ve worn Boden to nearly all special events in my young adult life—and always receive a handful of compliments. And they’ve absolutely mastered the shirtdress in all its forms. While their dresses are on the more expensive side of this list, they always have a thriving sale section, especially if you’re keen enough to buy dresses out of season.

Dressed Boutique

Dressed is the boutique you’ve never heard of. Many of my long-time favorite dresses are from the aptly named Dressed, and it’s easy to see why with their blend of timeless style meets modern chic. Based in northern Michigan, you’ll see dresses you’ll covet all year ‘round with their flattering sweater dresses, too. Not only will you support a small business (in a small town) by shopping here, but you’ll snag unique finds that you can bet no one else will be wearing at any wedding you attend. They don’t have an e-commerce site, but you can shop their Instagram by calling, messaging, or emailing to purchase.


It’s never been harder to go to Target “just for diapers”. If you haven’t seen the women’s section lately, here’s how my two-year-old put it recently: “Mama likes to look.” And after you see their styles and prices, can you blame me? Target has nailed the popular upscale-casual, midi/maxi, tiered, one-and-done look that you can wear to church or for an afternoon stroll. And with Target prices and inclusive sizes, what’s not to love. Plus, they have rotating collaborations with various designers for limited-time occasion pieces (I wore one to my baby shower) at a slightly higher price point (that’s still well-within a Target budget).

Piper & Scoot and Roolee

Piper & Scoot and Roolee have a similar feel and price point: slightly boho, modest, and on the more casual side. And as a woman who’s either been pregnant or nursing for the entirety of the last three years, I greatly appreciate a dress that doesn’t sacrifice style for function. These shops are both a one-stop-shop for both the recent college grad on a tight budget looking for an occasion dress and the pregnant or nursing postpartum mama who loves fashion but also wants to be comfortable.

Morning Lavender

The collection of pastels, soft florals, and romantic styles makes it feel like they nailed the brand name. I tried this new-to-me, wallet-friendly brand last summer and was quite pleased. After purchasing last year’s midi-version of this white dress, I found myself wearing it as a swim cover-up and on dates, to give an idea of the ease and quality.


Poshmark is the place to buy an occasion dress for less with pre-owned or gently used items. The recently closed, wildly popular Gal Meets Glam collection (that made dresses exclusively) can still be found in droves in a whole host of sizes on Poshmark. Poshmark is a destination spot for designer gems for less for your wedding guest, bridesmaid, or New Years Eve dress needs.

J.Crew Factory

Although it’s more expensive big sister might be well-known, J.Crew Factory offers many of the same coveted styles, with a much more reasonable price tag. Couple that with the fact that they always have sales (big sales!) there’s a reason that several of my day dresses are from here. Don’t expect to get your next occasion dress from Factory, but simple, casual dresses are their jam.

Draper James

Reese Witherspoon’s Draper James reminds me of the late Gal Meets Glam Collection—upscale dresses with classic southern sophistication and a slightly higher price tag. Like GMGC, expect lots of feminine ruffles, florals, bows, seersucker, gingham, and buttons done tastefully with longer hemlines. They also have a plethora of the ever-flattering wrap dresses.

LIV Maternity + Beyond

Pregnant moms deserve to experience the benefits of affordable, fashionable, quality dresses, too. Yet all too often I hear (and have experienced myself) that maternity clothes, including dresses, are either way too expensive for the short time that you wear them, or not good quality, or just plain frumpy. Thankfully, I discovered the new maternity and nursing (and beyond) line while pregnant with my second! I finally found a beautiful, comfortable, maternity dress to wear to a wedding. Pregnant moms will love these gorgeous dresses for baby showers, maternity photos, weddings. And being in a season of life in which my body has changed so much in a short time, the flexible, fashionable styles are ones I’ll keep coming back for—pregnant or not.

Gibson Look

Another new-to-me brand, Gibson Look caught my eye with their clean, polished website, something I don’t often see for brands of their price point (all dresses are under $100—and that’s before sale prices). The dresses are not particularly unique (read: they’re on-trend and mostly come in solid colors) but if you’re looking for a smart, classy dress that won’t break the bank, Gibson Look might be the winner.

Ever Thrift

If the fact that Ever Thrift is run by one of the founders of Verily isn’t reason enough to support them, then maybe the sustainable approach in a world of fast fashion is. Though I’ve never been a big thrifter myself, Janet takes the guesswork (and the work) out of thrifting with her incredible finds. Her hauls inevitably include unique and size-inclusive dresses—from night-out gowns to day dresses you literally can’t find anywhere else. And, of course, all at an affordable price.

Dresses are my personal weakness. Can you blame me? I don’t think any other article of clothing can convey elegance, timelessness, and style with such ease. For that reason, I can confidently say that I will always obsess over a dress.