Favorites In Gabi Gregg’s Wardrobe Wearable Items

Gabrielle Gregg started her blog in September 2008 and has since become a well-known influencer championing body diversity in fashion. “I knew firsthand the lack of resources for younger, modern women ages 14 and up, so I decided to fill the gap,” she writes on her website. Gregg, who has 664k followers on Instagram, has stayed true to his mission, launching collections with Swimsuits For All (the brand offers sizes 4 and up) and Playful Promises, a line of lingerie with expanded sizes. She ventured beyond collaborations and, in 2017, co-founded Premme, a clothing brand specializing in fashion pieces for women of all sizes.

It’s a funny thing. The pieces that get the most wear in my wardrobe are probably the ones I share the least around here. There’s a huge amount of pressure as a creator in any sector to start and facilitate fashion trends. At every change of the season I find myself torn between creating content that’s hot in the moment to boost my stats and staying true to my own fashion sense with neutrals and basics and cozy, casual pieces.

Most of the time, I stay true to my own style and share only things I actually love and wear but a few heroes of my closet have not often had their time to shine. Let’s give them a moment, shall we?

  1. J.Crew Chelsea Rain Boots

I wear these outside working in the yard and they are the perfect slop around the garden shoe. They hose off, are very comfortable, not too hot or heavy.

I bought these at J.Crew Factory for under $40 – currently only $38. Fits true to size

  1. TOMS Sicily Sandals

I wear these every day in the summer for the past 2 summers. I’m not kidding. They’re my go-to, go with everything, so comfy, summer sandal and I wear them to death.

Worth every penny and I will repurchase when mine fall apart. Find them at Nordstrom.

  1. Aerie Leggings

What would work from home life look like without a solid pair of leggings? I can’t say enough good things about leggings from Aerie – actually all of their clothes are really good. I always buy black leggings and these are my favorite by far.

  1. Shein Straight Leg Jeans

I don’t think I would buy anything from that website anymore, honestly, but a couple years I wanted to try out the straight leg jean trend without spending much money and to be honest I still reach for these jeans a lot. I don’t think they have the exact pair anymore, but these are similar. Shop at your own risk on this website.

  1. Thrifted Denim Shorts

My favorite pair of denim shorts are from a thrift store. I bought them years ago for maybe $4 and they’re the ones I always reach for if I’m wearing shorts. Don’t underestimate the power of a good pair of thrifted denim.

  1. Aritzia Sweatshirt

Think of the coziest piece of clothing you own then double it. That’s the comfort level of my Aritzia sweatshirt. It’s so good and I wear it all year round with everything from skirts to leggings.

  1. Madewell Grey Tee

Madewell Tees are some of my favorite affordable (but don’t fall apart in a year) t-shirts on the market. I bought the Vintage Tee (a boxy fit) in a size Medium to be oversized earlier this year and it’s perfect for that tucked into high-waisted jeans look.

  1. Grayson Hero Button Up in Strips ( currently on sale!)

If I’m needing to dress it up a bit my Grayson shirts are the first ones I reach for. They’re so soft and comfy and perfect to dress up pretty much any outfit. Yes, including leggings.

  1. Portland Leather Tote

This was a gift last year from the brand (see the post here) and I “wear” it every time I’m going out. It has this really handy leather loop with a snap on the inside that has kept my masks safe and clean and ensures I never forget them!

  1. Tan Baseball Hat

I have so many hats, but the one I reach for the most is my tan suede baseball hat. It goes with everything and makes me feel sporty. I’m sure the exact one is sold out, but here’s a similar style.


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