40 Dresses You Can Wear With Sandals Now And Boots Later

Soon you'll see your two fall BFFs: a pair of ankle boots and light jacket.
Floral dress, tie dye dress and bohemian dress.

Popular items from this list:

  • A cherry-picked frock in case you need yet another ’90s-inspired thing in your closet.

  • A striped beauty (OK, it’s in some solid colors too) if you prefer keeping things as comfy as possible.

  • A strappy casual dress can really help you show off some of the local plant life.

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1
A cherry-picked frock in case you need yet another '90s-inspired thing in your closet
Promising review: "This looked so cute on me! It fit perfectly! I just can’t wear a super padded bra but I don’t mind that. The material isn't bad either for what you pay." — JH
2
Elizabeth Lilly / BuzzFeed
An airy nap dress I own and plan to wear into fall with a moto jacket and ankle boots
I know, I look SO elegant and not at all like I've been running on three hours of sleep a night for going on a week at this point of my vacation, right?! I packed it for Italy knowing that I'd be going in lots of churches and religious sites that require having your shoulders and knees covered, and I pulled it off with this by merely slipping the sleeves up higher. But I owned this dress months before I touched down in Rome and have been racking up compliments from strangers on the streets of NYC thanks to this frock. ("Thanks! It's from Amazon!') It washes well, is super lightweight, and very easy to wear with a regular bra. The only thing it doesn't have is pockets. But I'll make an exception for this comfy beauty.
3
A striped option (OK, it's in some solid colors too) if you prefer keeping things as comfy as possible
Promising review: "The dress is the perfect length for work and isn't see through at all. I love black and white stripes and this dress, also, pockets!" — Brinna Kerrick
4
A tie-dye maxi dress you'll don on the couch, then show off while you pick up your farmers market haul
Promising review: "I love this maxi so much! I've had it for a couple of years now. It is so lightweight and perfect for hot summer days, but is also great paired with a jean jacket or cardigan in the fall. I love the functional pockets. LOVE that it is not sheer at all and holds up AMAZINGLY wash after wash. It is a little oversized, so I would definitely size down. I have it tied up in the front for looks and because it does drag a tiny bit on the ground." — Amazon customer
5
Amazon
A printed option to please folks who like some fabric on their arms
Promising review: "I searched out this dress after researching the wardrobe of Judy Hale on the Netflix show Dead to Me. I love her modern boho style. This was worn in one of the first episodes. After reading the other reviews about size, I ordered the XL. I am typically a US size 8 and between a M and L in most big brand sizes. The XL fit exactly how I wanted. I paired mine with a brown suede belt. The slit falls a little too high for me so I will probably sew it about 1" below the buttons. In my opinion, the buttons are a bit cheap, but not too bad. I believe this fabric to be 100% rayon challis (approx 140gm/m2). It's soft and flowy but not too sheer with this print." — bFranj
6
Or a shorter, similar boho dress that'll be a breezy, photogenic option
Promising review: "Wearing it on a trip to a hot climate. I appreciate the coverage without being overheated. It is very loose fitting. Hang it up to dry." — A.B.
7
A strappy casual dress can really help you show off some of the local plant life
Promising review: "I’m obsessed with this dress! It's so light and so comfortable! I bought the sapphire blue and I'm going to buy the black and potentially the green as well!" — Morgan Tecchio
8
A waffle-knit dress (with pockets) for a super cozy option
Promising review: "Turned out perfect! It's surprisingly lightweight, extremely comfortable, and easy to style. I ordered my normal size and it fit exactly as advertised. I'm a fan of comfy fashion so this was right up my alley. AND IT HAS POCKETS." — Mariah
9
A shorter gingham option with tiers made for twirling
Promising review: "I LOVE this dress!! The material is so lightweight that it’s perfect for summer, and then the buffalo plaid will also look cute and trendy in fall with a jean jacket! Plus I LOVE that there are pockets. The dress is made really well; I was pleased to see it also had a lining so it’s not at all transparent. I saw another review that said it ran a little small and as someone between two sizes I sized up and I’m glad I did. I like that it is more flowy and comfortable-fitting! I will be wearing this dress all summer and then some!" — Theresa St Peter
10
A solid option you'll love
Promising review: "This is very comfortable, long (which I am so thankful for, as I am 5-foot-9), and fits me well. I can dress it up or wear casually. I really enjoy the comfort of it and how it can be worn during many seasons. It's a great price, length, and fit. I definitely recommend." — Faith
11
A striped cap sleeve midi
Promising review: "This summer dress is a must have! I must have worn it at least once a week all summer long. It’s so comfortable and the material is breathable.. even on humid days. The pockets are ideal and the flutter cap sleeves couldn’t be cuter. I wore it with white sneakers, sandals and espadrilles so it’s very versatile. Looking forward to pulling it out of the closet next summer." — Nikki Scott
12
A casual striped option with some ruffled sleeves to make it feel a bit special but not super dressy
Promising review: "This dress was perfect for our beach vacation. Light weight yet not too thin...you could not see through the dress so it was perfect for the hot weather!! High recommend!" — Amazon customer
13
Amazon
A tie-strap dress in an ankle-grazing length
Promising review: "I absolutely love this dress! It’s comfortable but also looks chic. I feel like it could be easily dressed up or down. I’ve worn mine as a halter and regularly tied as pictured. It does run a bit large so I would size down if you’re in between sizes. I ordered another color after receiving mine because it’s so great!" — Ally Estergard
14
A bodycon midi dress that'll look oh-so-glamorous at that fancy dinner you're going to
Promising review: "I am in love with this dress! It is so soft and stretchy but looks sexy and chic even though it’s only $17. It wasn’t see through at all. It hit me at the perfect midi length and it was great being able to slightly adjust the straps. I wore it with nude heels for a fancy dinner out and got so many compliments, but it would also be great layered with tights and boots and a sweater for fall/winter. I 100% recommend this dress! Best Amazon purchase ever! I can’t wait to wear it again." — Sarah L.
15
A leopard slip dress with an alluring slit you'll have to hide from yourself occasionally
Promising review: "BUY THIS DRESS!!! Omg I'm so happy with this purchase! The colors are beautiful and would look stunning on any skin tone! It is lightweight but lined, so its perfect for the beach / summer time. Definitely needs to be steamed before wearing so keep that in mind! But you will not be disappointed." — Amazon customer
16
Amazon
A breezy midi dress to keep you looking carefree
Promising review: "I love that this dress is comfy, inexpensive, and perfect for a casual outfit. As a mom of two, I am always looking for cute things to wear without much thought. This fits the bill! For reference, I’m 5'5", 125 lbs. and purchased the small." — AMCase
17
Amazon
A cute mini floral dress
Promising review: "This dress is sooooo cute! I got a ton of compliments on it when I recently wore it to a baby shower. Loved the soft material, and it can easily be dressed up or down, from work to brunch. I bought my normal size, it fit perfectly. But I could have probably got away with a size smaller. Will order another color." — Elizabeth
18
Amazon
A bodycon T-shirt dress with a tulip hem for wearing with sneakers or ankle boots
Promising review: "This dress is phenomenal. Not see through at all (I did buy black, though), and it is lined. It’s also extremely comfortable. I plan to dress it both up and down either for work or casual outings. I’ll admit I was skeptical, but I definitely won’t be returning this dress. And as many have stated it looks much more expensive than what it goes for." — KG
19
A work of art (more or less) might just have people thinking you paid a devastatingly high price for it
Promising review: "BUY THIS DRESS!!!!!! You guys it’s SO PERFECT. I’m a size 6/8 and I got a 6. It fits perfect. It's a little tight on the chest, but I’m a DD, and it still fits. The dress is quality and literally the cutest dress I’ve ever bought. I'm ordering every color!!!!!!" — Elizabeth Novak
20
Amazon
A solid dress with pockets for so much wardrobe versatility, you'll wonder why you didn't buy it in every color from the start
Promising review: "This dress is beautiful. It is generous in size. I should have gotten a 2X instead of a 3X. Color is beautiful, the material lays well, the craftsmanship is great. Well worth the purchase." — Oneladya
21
A pretty baby doll dress
Promising review: "This dress is adorable!! I am 5’6” 116lbs, 34B chest, generally a size small in dresses. I originally ordered the white/black polka dots in a Small and it was way too big so I exchanged for an XS in black/white polka dots. Both colors were so cute!! Material has stretch to it and fits very babydoll like. I’ve ordered dresses from Romwe before and they never disappoint! Definitely recommend!!" — Lindsay
22
Amazon
A snake-print midi sure to slither its way into your regular outfit rotation
I have this dress in the green and it looks SO good IRL!
23
A flowy boho style you can get a ton of use out of every season
FYI, reviewers say it runs a tad big because that's the style.

Promising review: "Bought this to wear to a concert and it was perfect! It does run a little big but not so big that you need to exchange. Super comfortable! Love it!" — Amazon customer
24
Amazon
A ruffled masterpiece passersby will think you spent $$$ on
Promising review: "Love this dress, modest enough to wear for work but cute enough to wear every day! I'm petite so I would say it runs a bit bigger than I'd prefer but it is still super cute! Also, this exact dress is being sold at other boutiques for three times the price!" — Emily Seils
25
A high-neck dress you simply must post on your Insta
Promising review: "YES!!! SO MANY TIMES YES!! Loved it. This dress was beyond — the color was amazing; the amount of heads I turned in the office was wow, and the compliments just kept on coming. I absolutely love this dress, and I didn't want to take it off at the end of the day. Comfortable, lightweight, easy, absolutely beautiful, and true to size." — Mushka
26
A flowy ruffled-hem dress
Promising review: "I absolutely love this dress — it fits perfectly and it's so adorable. The first day I wore it I got so many compliments and it was so comfortable. It was nice to wear as a dress or even a long shirt with leggings. The color is really cute too. I definitely recommend it and will probably buy more in different colors!" — Jasmine Ball
27
Amazon
A flowy shift dress
Promising review: "I was skeptical when I ordered this but OMG it is my favorite dress right now. So flowy and pretty." — Crystal
28
A fitted ruffled wrap dress
Promising review: "Usually I find that the clothing off Amazon doesn’t always fit well but this dress fit basically perfectly! It is pretty true-to-size. The fabric does not have any stretch at all so you want to be sure to order the right size. Also, the color is a little more vibrant than the picture on the site." — Tori H
29
A long-sleeve faux-wrap dress you can buy in a range of prints
Promising review: "Super impressed with this dress! I looked at it and read the reviews so many times before just buying it, and I am SO glad I did! I wore it for a night out with my husband and got a ton of compliments. I have an athletic build (broad shoulders/average chest) and while it was very low cut, it was comfortable and still classy looking. Even at my height, I didn't feel like it was too short which can sometimes be an issue... bottom line, buy the dress!!! I'll be ordering it in more colors!" — 14AnnaM
30
A very comfy T-shirt dress with a tie
Promising review: "I said 'it's comfortable' like 10 times when I tried it on because that's how comfortable this dress is! It's a soft T-shirt material and it runs true to size. I love the tie in the front. I could live in this dress!" — Cyndi Lundeberg
31
A lantern sleeve mini dress
Promising review: "This dress is SOOOO adorable. Absolutely in love. Gives very old fashioned feels and I'm all for it! I got the light blue and I'm definitely buying in more colors. Worth every penny." — Olivia
32
A short-sleeve skater dress that'll work for basically any warm-weather activity
Note: The buttons aren't functional, they're just for design.

Promising review: "I love this dress! I can wear it to work, dress it up a little or just keep it casual. And I have a large chest and I don’t have to worry about the buttons popping open because they’re not functional and that’s the best part!! I’m ordering another one in a different color." — Jennifer
33
A V-neck dress
Promising review: "I love love love this dress. I wore it for Easter this year and got so many compliments. My ONLY complaint is the boob area. However, this was only a complaint on Easter when I would have like to have been more modest. I had to pin the dress in the cleavage area to make sure the girls were covered. Since then I have bought another dress in a different color and I'm excited to wear them this summer! BUY THIS DRESS. if you’re second-guessing whether or not to buy it, BUY IT." — Rhianna Hill

Before You Go

A set of two pairs of silicone heel cups

Heel protectors to wear all fall long

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