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Unless otherwise specified, all sizes in this post are listed in women's.
1. A turtleneck knit dress because it's basically your favorite and coziest oversized sweater turned elegant, chic, fancy dress. Wear it with tights on the *coold* days or just wear it with your fave boots on the ~cool~ days.
2. A puff-sleeve dress that can be worn anywhere from a backyard wedding to a backyard barbecue. It's graceful yet casual, classic yet trendy — truly an enigma — it all just depends on how you choose to style your lower half.
3. A knit turtleneck dress you can wear for a winter date night...and continue to wear when you and your S.O. ultimately decide to stay in and order DoorDash instead. (Pro tip: DoorDash is best enjoyed without the limits of a waistband, leave the tights at the door).
4. A tie-waist batwing sweater dress that'll pretty much have you looking put together no matter what. Wear it with boots or slippers, you have no choice but to be look fashionable. Doesn't matter if you put close to zero effort into getting dressed.
5. A sweater dress because it's a dress with tights and a sweater with leggings. It's literally exactly what it says it is. I wish everything was this cut-and-dried.
6. A waffle-knit tie dress on the same comfort level as your favorite thermal pajamas. The only difference is that the dress is very stylish (my apologies to your PJs).
7. A ruffled-hem dress that's definitely what Sixpence None the Richer had in mind when they sang, "Swing that spinning step, / you wear those shoes, and I will wear that dress." To this day, I'm not sure what a swinging step is, but you should buy this dress, wear it while playing that song, and find out.
8. A super cozy oversized sweater to wear with some tights and knee-high boots, allowing you to circumvent the "dress code" your friends had in mind when they said "dress up" for your GNO.
9. A cinched-waist, button-down shirt dress that'll let everyone know you mean business...Risky Business, that is — or maybe regular business, (teetering on risky) when paired with some tights...Either way, you'll be living out your '80s rom-com dreams.
10. A U-neck mini dress that can be worn with sneakers, sandals, or boots, making it not just appropriate for any occasion, but any season, too.
11. A collared flare dress because I can't decide what's cuter — wearing it with white socks and oxfords or pairing it with sheer black tights. Buy it once and wear it both ways (for me, please).
12. A floral mini dress that embodies spring, but can be worn *way* before spring finally arrives when you wear it with some shimmery white or black sheer tights.
13. A V-neck button-down dress for the days when you're feelin' prim and proper. You can wear it with some white ankle socks or tights...or...now stick with me...wear it with both. So cute.
14. A ribbed corset dress because it's pretty much loungewear until...(you probably already know where I'm going with this) you slap on some tights.
15. A long-sleeve T-shirt dress that is absolutely necessary for any wardrobe given the endless outfit possibilities. It's understated, allowing you to style however you see fit, with the *utmost* of ease.
16. A chiffon slip dress you can buy now and wear now by layering, and then finally give it a *proper* debut on its own when it's summertime. Something to look forward to.
17. A corduroy overall dress because overalls are seasonally and situationally universal. And whatever you decide to wear under it — long-sleeve, short-sleeve, tights, highs socks — always looks really, really cute. Btw, this particular dress also has pockets, ya know, in case you thought it couldn't get any better. It can.
18. A wrap dress that'll have you looking forward to a day at the office. It's a lot easier to get out of bed when you have a stylish outfit picked out for the day...and even if the weather catches you off guard in the morning, a pair of opaque tights'll do the trick. Rain or shine — you will carry on, you will wear this dress and you will feel good.
19. A zip-up dress aka a genius combination of the beloved bodycon and the even more beloved quarter-zip. Wearing this with a baseball cap and some sneakers is probably the cutest casual outfit known to man, but dressing it up for night out will make you feel like a million bucks. Can you say "range?" because this thing's got it.
20. A roomy plaid shirt dress so you can remain casual, laidback, and comfortable all while wearing something other than the usual old T-shirt/sweatpants combination. Yes, I'm saying this dress has the same effect.
21. A mini slip dress you can throw over the T-shirt you're already wearing because you're too lazy to change out of it orrrr with some tights and pumps because you feel like getting all dolled up! Whatever mood you're in, this dress will be there for you.
22. A denim shirt dress because what could possibly be more effortless than a T-shirt and a pair of jeans? The answer is combining them into one article of clothing... AKA, this dress.
23. A swinging faux-wrap dress available in so many great prints, you probably should buy one in every color, basque in the all the ways to style it, and wear only this dress for the rest of your life.
24. A pocketed and belted sheath dress that gives you options. You can wear it off the shoulder if you wanna ~show off a 'lil skin~ or as a classic boat neck if you wanna keep it more modest. You could cover up with some tights or pair it with flats and give a lil' leg.
25. A sweatshirt dress — the T-shirt dress' cozier (yet equally as cute and versatile) cousin.
26. A flowy but fitted wrap dress because the ruffles alone will bring you joy every time you make any type of movement. And don't worry, you can dress it up or down, so you'll always have an excuse to wear it. Ruffles may be the key to happiness. Let's put my theory to the test...
27. A ribbed V-neck skater dress in case you consider yourself ~too cool for school~ and up until this very moment, you thought you were too cool to wear dresses. Rocker chic, meet flowy skirt. Legs meet sheer knee highs.
The reviews for this post have been edited for length and clarity.