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October Outfit Diary

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In my first outfit diary post last month, I was most excited to hear that it helped encourage some of you to rethink your favorite wardrobe essentials and consider new ways to wear them. I always love coming across an outfit online and realizing I have super similar pieces in my closet! Wearing the same pieces in all different ways is really the beauty and the challenge of a capsule wardrobe lifestyle, and something I think about often. You’ll see lots of repeat pieces below, but I hope that that is part of the fun of reading this post!

While I hope this post is much more of an idea resource than a shopping one, I do hope to make it as useful as possible. You’ll see that I added sources, sizing details, and similar items below so that if there is a staple you’re looking for, you’ll have my full review of the pieces I’m personally wearing and loving at your fingertips.

Blush knit cardigan for fall | Something Pretty J. Crew Factory cardigan: One of my favorite fall purchases! I love the color and the chunky knit look. I sized up to a large for a cozier, longer fit / J. Crew Essential tee: White tees are such a staple for me, I reach for them as soon as they’re out of the wash. This is my favorite one I own right now! I sized up to a large because I prefer my tees to have a looser fit. / J. Crew Factory jeggings: Finally decided to buy a not-too-expensive pair of jeans in a size up from my pre-pregnancy size so that I can do things like sit down comfortably this season ;) These are stretchy and comfy and I love the high-waist, especially postpartum. Wearing a size 28 and think they fit true to size. / Veja Esplar sneakers: I love these sneakers so much! Super classic, beautiful quality, and very easy to style with anything from jeans. to shorts, to dresses.

J. Crew New York sweatshirt | Something Pretty J. Crew New York sweatshirt: I’ve had this for a few years, and although it’s out of stock at the moment, they bring it back every once in a while! One of my favorite comfy, casual tops. Wearing a medium. / Zella Live In High Waist leggings: By far my favorite leggings I’ve ever owned. Thick but not too hot, opaque, high-waisted, and not shiny. Wearing a small. / Allbirds Tree Runners sneakers: My brother used to work at the AllBirds store in Austin, so these feel a little sentimental! Sentiment aside, these sneakers are SO comfortable and I love being able to wear them without socks. / Loft velvet headband: Lots of headbands give me a headache by the end of the day, but this one from Loft doesn’t. The black velvet is out of stock, but here is a black one, here are the other velvets, and here’s a different black velvet.

How to style Veja sneakers with shorts | Something Pretty Vince long-sleeve tee: I bought this slouchy tee for my first branding shoot and still wear it often–the color is so perfect. This is the closest thing I can find in stock. / J. Crew shorts: Yup, still wore shorts quite a bit this month! These have a high rise, perfect for front tucks, and a classic wash. / Veja Esplar sneakers: I love these sneakers so much! Super classic, beautiful quality, and very easy to style with anything from jeans. to shorts, to dresses. / Draper James magnolia earrings: My favorite alternative to my usual pearl studs.

Classic outfit with leopard mules | Something Pretty J. Crew Essential tee: White tees are such a staple for me, I reach for them as soon as they’re out of the wash. This is my favorite one I own right now! I sized up to a large because I prefer my tees to have a looser fit. / J. Crew Factory jeggings: I finally decided to buy a not-too-expensive pair of jeans in a size up from my pre-pregnancy size so that I can do things like sit down comfortably this season ;) These are stretchy and comfy and I love the high-waist, especially postpartum. I’m wearing a size 28 and think they fit true to size. / Old Navy leopard mules: My cost per wear of these budget-friendly mules is in the fractions of a penny. I bought them last fall and have been reaching for them just as often this year!

How to style Sam Edelman Loraine loafers | Something Pretty Loft blouse: I bought this flowy, Victorian-inspired blouse when I was pregnant–you may remember if from this post! It’s out of stock, but this, this, and this have a similar look and feel. / J. Crew wool skirt: I have had this skirt since college! I hadn’t worn it in a while but reached for it to wear to church since I’m bored of all my nursing-friendly church dresses (I have actually never had to nurse in church, but want to make sure I can if I need to!). It’s a classic piece that has held up well for going on a decade. / Sam Edelman Loraine loafers: One of my favorite pairs of fall shoes, these loafers have held up beautifully over the two years I’ve had them. They come in a bunch of different colors–mine are the Saddle Leather.

Olive Clothing Sophie striped tee | Something Pretty Olive striped tee: I shared a bunch of my favorite Olive pieces in this post and bought this striped tee soon after. I really like the boxy (but not short) cut and thick fabric. Note that it’s a “one-size” piece, so it’ll look different on everyone! / J. Crew Factory jeggings: I finally decided to buy a not-too-expensive pair of jeans in a size up from my pre-pregnancy size so that I can do things like sit down comfortably this season ;) These are stretchy and comfy and I love the high-waist, especially postpartum. I’m wearing a size 28 and think they fit true to size. / Margaux Demi flats: The perfect, classic ballet flats. Margaux’s quality and fit are second to none! The Demi is one of their lower-priced silhouettes, so they’re a great introduction to the brand. Use the code LISA for 10% off your first order. / Plaid headband: This might be from high school..? I have always loved headbands so I’ve hung on to them, even when I’m not wearing them much.

Madewell bobble cardigan | Something Pretty Madewell bobble cardigan: My most-worn item from last fall/winter and still a favorite! I love how it looks with and without a bump :) / J. Crew Factory Girlfriend tee: Another white tee in my closet, this one has a bit of a heathered look. I prefer the Essential tee, but this one is fine as a back-up. / Zella Live In High Waist leggings: By far my favorite leggings I’ve ever owned. Thick but not too hot, opaque, high-waisted, and not shiny. Wearing a small. / Old Navy leopard mules: My cost per wear of these budget-friendly mules is in the fractions of a penny. I bought them last fall and have been reaching for them just as often this year! / Chews Life rosary bracelet: I got this as part of the Blessed Is She Advent bundle, and even though the exact one is sold out, you can find lots more styles and colors here. The cross charm on it is movable so you can use it to mark your place.

How to style Hunter boots | Something Pretty J. Crew Factory cotton-wool Teddie sweater: I’ve been stealing Dave’s gray crewneck sweater for years and finally decided it was time to get my own ;) Wearing a medium. P.S. Do NOT put Teddie sweaters in the dryer–they shrink like crazy if you do. / Zella Live In High Waist leggings: By far my favorite leggings I’ve ever owned. Thick but not too hot, opaque, high-waisted, and not shiny. Wearing a small. / Hunter rainboots: I snapped these up at Costco, of all places! They’re such a classic style and are durable enough to hopefully last me for decades. / Loft velvet headband: Lots of headbands give me a headache by the end of the day, but this one from Loft doesn’t. The black velvet is out of stock, but here is a black one, here are the other velvets, and here’s a different black velvet.

How to style white pants for fall | Something Pretty J. Crew Factory cotton-wool Teddie sweater: I’ve been stealing Dave’s gray crewneck sweater for years and finally decided it was time to get my own ;) I opted for a medium for a looser fit. P.S. Do NOT put Teddie sweaters in the dryer–they shrink like crazy if you do. / J. Crew Factory white corduroy pants: I love the way the corduroy makes these white pants perfectly fall-appropriate, while the high-waist button front is a fun twist. These run small–I had to return and exchange a pair before landing on one that fit. Wearing a 29. / Captoe pumps: These block heels add the prettiest, most classic feel to any outfit. I wore them to dress this look up for church. My exact pair is sold out but these, these, and these are almost identical. / Loft velvet headband: Lots of headbands give me a headache by the end of the day, but this one from Loft doesn’t. The black velvet is out of stock, but here is a black one, here are the other velvets, and here’s a different black velvet.

J. Crew factory high-rise jeggings | Something Pretty H&M polka dot blouse: A friend gave me this top from her closet when I was pregnant because it’s long in the front and back, so she thought it would be cute with a bump. Nowadays, I wear it tucked in the front. Love this and this polka dot top too. / J. Crew Factory jeggings: I finally decided to buy a not-too-expensive pair of jeans in a size up from my pre-pregnancy size so that I can do things like sit down comfortably this season ;) These are stretchy and comfy and I love the high-waist, especially postpartum. I’m wearing a size 28 and think they fit true to size. / Old Navy leopard mules: My cost per wear of these budget-friendly mules is in the fractions of a penny. I bought them last fall and have been reaching for them just as often this year!

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  1. Em says:

    Declaring my love for this series once again! Might have to twin with you in those cords…

  2. Dana says:

    Those cords are cute!!

  3. […] here too. For more styling ideas for these flats, see how I’ve worn them in my September and October outfit diaries, with a dress, with jeans and a cozy sweater, out for drinks, and in the summer, to […]

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