3 Effortless Summer Outfits for Fashion Challenged Boss Ladies (summer outfit ideas)

Last updated on March 6th, 2019

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Everybody loves looking stylish, including those of us who aren’t gifted with the “style gene.”

Fashion has never been my forté. I tend to wear whatever I want, whenever I want, uncaring of how I fit each piece into a look. For example, if I felt like wearing a crazy colorful skirt, it would automatically end up paired with a plain white shirt because I didn’t know how to match it with anything else. And jewelry? That was for super special occasions only.

I know all you fashionistas are laughing your butts off at me right now, but that’s okay. From now on, I am aiming to create different looks that are stylish and comfortable, but don’t look like I’m trying too hard. This is Hawaii- nobody wears Louboutins, and I have never seen a Céline bag on these streets.

Oh, and one more thing, this is my first fashion lookbook ever, so go easy on me. I’m still practicing my posing and working out the photography kinks.

Let’s get started!

Look #1 “Shopping chic”

This outfit is super casual and perfect for hanging out on the weekends. My flowy tank and stretchy jeans make movement very convenient, and the half-tuck gives it that “I’m just effortlessly cool” vibe. I went with my bright blue sneakers to add something funky to this otherwise pretty basic look. Spice it up even more with statement earrings, a simple necklace, and a stylish belt.

Look #2 “Brunching & lunching”

What says summertime more than brunch? I wear outfits like this when I want to look slightly dressed up, but not so fancy that I wouldn’t feel comfortable walking around in the mall afterward. My fit & flare dress is from H&M, and my mini denim jacket is from Target, (similar items below.) I live in a super casual environment, so I dressing down my girly dresses with Keds and backpack purses, but you can easily add cute heels and a satchel for a totally different look!

Chaps Floral Sateen Fit & Flare Dress (similar) >> KOHL’S

Mossimo Denim Jacket in Medium Blue (similar) >> TARGET

Keds Champion Oxford Sneakers in Navy >> MACY’S

Stud Embellished Backpack (similar) >> EXPRESS

West Coast Jewelry Stainless Steel Heart Charm Bracelet (similar) >> TARGET

Lucky Brand Silver Tone Feather Earrings (similar) >> NORDSTROM RACK

Lafonn Birthstone Pendant Necklace (similar) >> NORDSTROM

Look #3 “Going out in style”

This grandma must be comfortable if there’s any chance of getting her out of the house in the evening. Thanks to the humid summer temps and my dislike of constantly babysitting skirts, shorts are the way to go! These black linen shorts pair perfectly with the elevated button-up blouse and shiny accessories. My patent Oxford pumps complete the menswear vibe for a casual & cool evening look!

Slim Fit Polka Dot Portofino Shirt >> EXPRESS

Linen-Blend Short in Black >> EXPRESS

Shiny Airplane Layered Necklace >> EXPRESS

3 Pack Patent Skinny Waist and Hip Belts (similar) >> ASOS

Ball Stud Earrings 6mm 14k Yellow Gold >> KAY JEWELERS

Clarks Tarah Victoria Pump (similar) >> NORDSTROM

Shelly’s London Frankie Oxford (flat option) >> NORDSTROM

That’s all for today!

Like this post? Head over and enjoy this one too >> 18 Nifty Ways To Use A Scarf When Traveling

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Till next time. ♥︎

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FTC- Not sponsored by any brands mentioned. I purchase all products myself. All opinions are my own. Some links may be affiliated.