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Unless otherwise specified, all sizes in this post are listed in women's.
1. A pair of espadrille wedges to wear when sandals aren't dressy enough, but heels are too dressy for where you're going. These are the perfect combo of comfy, cute, dressy, and summery!
2. A pair of heeled Mary Janes with a cushioned footbed that are designed for a lot (and I mean a lot) of walking. Though these might not have as much pizazz as some of the other shoes on this list, they are a timeless classic that'll actually get the most use since you can wear them for literally anything.
3. A pair of classic pumps because they can and will last you a lifetime of occasions. Also, these come in every color of the rainbow, so you can easily find the perfect pair to match that vibrant floral dress you got ~just~ for the occasion.
4. A chunky ankle-strap heel designed to be slip-resistant in case you're a bit clumsy (honestly, same). These have a latex insole that contours to the shape of your foot, giving you that extra bit of comfort you'll need to get through the longest day of your life.
5. A pair of strappy heels that will actually be comfy all day and all night long. Plus, these have a solid block heel, so you'll have a little more stability if you end up imbibing a bit more than you planned. Just saying...they would look incredible with your Taylor Swift Eras tour fit.
6. A pair of funky-patterned heels with a bow in the back for all my fellow cutesy accent lovers. Not only is this a super sweet detail to jazz up a basic pair of heels, but the ankle strap is also removable, allowing you to turn them into pumps!
7. An adorable pair of retro-inspired kitten heels because look at them — it's a slay. Sophisticated and elegant, these are great for attending that lavish restaurant with a tasting menu you can't afford to go to (but are going to anyway, of course).
8. A pair of lace-up sandals that will look so sexy and sleek no matter what kind of dressy occasion you wear them to. These have a long strap that starts at the instep and goes all the way up to your calf, so however you tie them, your shoes will stay on until you get home.
9. A pair of pointy T-strap flats with all the sophistication of heels minus the height. Not only would these be awesome for a date, but they're also perfect for any up-and-coming wedding or even when you just want to get a little fancier in your everyday life.
10. A pair of shiny platform loafers if you want your feet to look ~sophisticated~ and feel comfortable. Something I love about these is the padding at your foot's pressure points and their soft insole, so you'll feel great, even if you get stuck at happy hour with that coworker you have nothing in common with.
11. A pair of peep-toe slingbacks because you finally splurged on a pedi for open-toe szn. With those solid ankle straps, your feet will 100% stay in your shoes no matter what kind of chaos the day brings.
12. A pair of simple-yet-chic braided sandals that'll have everyone asking where you got them. The sturdy block heels offer a little somethin' extra, making them look especially ~luxe.~
13. A pair of super strappy shoes with a lower heel, so maybe you won't sink into the ground while walking outside this week. It's the perfect lil' thing to zhush up a fit.
14. A pair of flat mules for people who want something that slides off as easily as they slid on. Soft and supportive, these dressy shoes are so easy to style that you'll wear them all the time — so much so that you'll completely forget you initially bought them for an event. With so many prints, styles, and color combos to choose from, you can 100% find a match for your aesthetic.
15. A pair of heels with super cool cutouts that look like they're straight out of the 1940s. Sometimes you just want to wear something a bit different, and this vintage-inspired find will surely have you smiling every time you look at them.
16. A pair of low wedge sandals if you're not into wearing heels for more than thirty minutes. These come in glamorous, sparkly metallics but also in more neutral styles so when you're not wearing them to an event, you can easily wear them with jeans or your favorite sundress.
17. A pair of chunky-soled heels because, TBH, you'd rather be wearing your combat boots RN. A modern take on the classic pumps, these will have the feeling ready to take on the world.
18. Or a more classic pair of pumps that show off a bit more of your foot. Not only are these a timeless style, but they were also designed to be super lightweight, so they won't feel like they're weighing you down as you try to slide away from that one person who won't stop talking.
19. A pair of flats with bows on the front to spice things up. Sometimes you just don't feel like wearing heels but are still looking for a bit of a formal look and these can easily give that for you. Just imagine how cute these would look with your favorite sundress!
20. A pump with an extra crossover strap to add a touch of sexiness to your outfit. Durable and flexible with a traction sole to help out my fellow clumsy peeps, this supportive piece will add a little pizzazz to your collection.
21. A pair of wedge-style ankle-strap flats that would 100% dress up any casual look. They are also designed with soft lining, which promises to keep you comfortable all day long.
22. A pair of rhinestone-bedazzled flats because sometimes, you just want to make a statement and be comfortable at the same time. Alexa play "Bejeweled" By Taylor Swift. Flexible and super soft, these luxe shoes are a winner in my book.
23. A pair of simple ankle strap sandals perfect for your next spring event. Designed to be lightweight and comfy, you cannot go wrong with these bbs! I should also add these have over 11,000 (!!!) five-star reviews! That's gotta count for something.
24. A pair of ballet flats with floral cutouts because they are equally as cute as they are comfortable. Heel me out, these with an eyelet dress or skirt would be so *chef's kiss*.
25. A pair of low chunky heels that have almost a mod vibe to them. Wear them with a '60s-inspired dress, and you'll look like you just stepped off the set of Mad Men. Fun fact: the square toe gives a little extra room in the toe box, which helps if you're a fellow wide-foot bestie.
The reviews for this post have been edited for length and clarity.