How To Wear Peep Toe Booties

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I’ve been obsessed over finding the perfect pair of peep toe booties since I first saw a pair on a stylish gal who was walking by when I was downtown a few years ago. When I saw this pair by Xappeal at Rack Room Shoes, I knew they were it.

How To Wear Peep Toe Booties 3 Ways / hellorigby!

Since I know these are a bit different from your standard pair of ankle boots, I thought I’d share how to wear peep toe booties in 3 different, winter-friendly ways today! 

How To Wear Peep Toe Booties: To a Party

How To Wear Peep Toe Booties: To A Party / Red Party Dress, Black & White Coat, Tassel Necklace, Peep Toe Booties / hellorigby!

Okay, I’m being brave and bearing my legs… then again it is about 50 degrees here. I think you could totally make this work if you’re in an even colder climate than mine by adding a fun colored tight. I’m usually not the biggest fan of peep toes and tights, but I think with the right tight it could definitely be a fun look!

What I’m Wearing:
Coat: Tulle via ThredUp (similar)
Dress: Express (sold out; similar)
Necklace: Sears (similar)
Bootie: Xappeal c/o Rack Room Shoes

How To Wear Peep Toe Booties: On a Casual Weekend

How To Wear Peep Toe Booties: For A Casual Weekend / & Tee Shirt, Black Leather Blazer, Leather Trim Track Pant, & Peep Toe Booties / hellorigby!

On the weekend, I like to dress much more casual. I think a nice pair of knit track pants dressed up with these booties is a fun look, and I like the touch of leather in the blazer, on the waist of the track pants, and in the bootie.

What I’m Wearing:
Track Pant: Golden Tote (similar)
Blazer: Kut from the Kloth
Tee: Honey & Hive (similar)
Earrings: Loren Hope via Rocksbox
Bootie: Xappeal c/o Rack Room Shoes

How To Wear Peep Toe Booties: For Any Day

How  To Wear Peep Toe Booties: Everyday Wear / Fur Vest, Black Sweater, Black Skinny Jeans, Peep Toe Booties / hellorigby!

I think a sweater and vest combo is perfect – it’s nice and warm up top, so if your feet get a little bit chilly your upper body can compensate. Obviously if it’s a blizzard, I wouldn’t recommend this outfit, but if you’re from a climate like mine (hi rain!) open toes are still do-able.

What I’m Wearing:
Vest: Vintage via Goodwill Glitter Sale (similar faux fur)
Sweater: Karen Kane 
Jeans: LC Lauren Conrad
Earrings: Loren Hope via Rocksbox
Bootie: Xappeal c/o Rack Room Shoes
Disclosure: Rack Room Shoes sent me these booties for review and styling, but no further compensation was received. All opinions are my own.

And if you’re still looking for your perfect pair of peep toe booties (or any other winter-friendly footwear!) Rack Room Shoes offers tons of great on-trend footwear and everyday “Buy One Get One 50% Off” promotion on all styles. Plus, sign up for the Rack Room Rewards® and get member’s only perks include exclusive discounts, coupons, and $15 in rewards for every $200 spent. Deals deals deals!

And with that, I hope some of these outfits will help you plan your dressing around the holidays! I seriously cannot believe Christmas is 2 days away. I need to get to wrapping!

Would you rock a peep toe bootie in winter?


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49 thoughts on “How To Wear Peep Toe Booties

  1. Natalie

    While you look absolutely adorable, I don’t think there’s anyway I could manage these. I am that person who freezes in 60 degree weather, and my feet are basically blocks of ice from November to April, even with the three pairs of socks I wear!

    Reply
  2. johanna

    I love that last look with the fur vest! I have been wanting a pair of peep toe booties for a few months, but my toes are weirdly short (seriously, really short) and don’t tend to “peep” at all. :(

    Reply
  3. Sarah

    You rock those boots really well! I am definitely not brave enough to wear them. I could see myself wearing them to a party, but I don’t think I’ve been to a party where those would have been appropriate in awhile.

    Reply
  4. Rebecca B. Bird

    Love these looks, especially the party outfit! I worry that my toes would fall off due to frostbite in the frigid NYC winter, but 50 degrees sounds like perfectly fine peeptoe weather! :)

    Reply
    1. Jenn Post author

      Thanks Rebecca! We definitely had some nice warm weather but now it’s back to being cold here too. Crazy winter weather can’t make up it’s mind! ;)

      Reply
    1. Jenn Post author

      Haha! I know what you mean. I have never done it, but I’ve seen others wear it and it especially makes me cringe when you see the tight seam in the toe area!

      Reply
  5. Myrabev

    You’ve dressed them nicely in all three outfits, I do not think I owe any I was actually eyeing some when I went shopping christmas eve. Happy holidays x

    Reply
  6. lauriel

    All three looks are so cute! I love peep-toe styles. Most of my booties/pump/stilettos/flats are peep-toe actually, because I have wider feet, and I found that peep-toe styles are more comfy in the toe area. They also allow cute, colorful pedicures to be showcased too. ;) So yes, I completely approve of peep-toes being worn in the winter.. and yes, I wear them with tights. Usually, with a lower denier, patterned tight…

    xo,
    lauriel
    EyeForElegance.com

    Reply
    1. Jenn Post author

      Wearing them with patterened tights sounds fun! I’ll have to expermiment with that. I have wider feet as well and like you, find peep toes are much more comfy!

      Reply
    1. Jenn Post author

      Thanks Katie! I can imagine peep toes are not appropriate for most climates this time of year ;) Love how you styled yours – the zippers on the front of yours are so edgy!

      Reply
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  8. TAMMY

    Yes I love peep toe booties and I wear them as long as there is no snow/ice on the ground and its over 30F. Weather permitting.

    Reply

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