What I Wear When I Want to Look Cute Without Trying (All Summer Long)

Photo Credit:@laurajadestone

I’m a layering girl at heart. I love layers. I live for layers. So much so that when summer hits, and it’s just me, a tank top, and some shorts I feel weirdly… underdressed.

And let’s be honest Chicago is known for its iconic hot girl summers. But this year? Mid-June wasn’t giving what it was supposed to give. Now that we’re in July, I’m hoping we finally get the vibes, the patio weather, the sunlight past 8 p.m. because I’ve got things to wear.

Between travel days and days where I just don’t want to sweat through another outfit, I’ve landed on a few go-to outfit formulas that make getting dressed so much easier. No overthinking. No trying on your whole closet. Just easy pairings that always work.

Wait, what’s an outfit formula?

Think of it like a recipe—but for your clothes. It’s a combo that you know just goes together. Like: relaxed tee + wide-leg pants + comfy sandals. Or midi dress + lightweight layer + a cute sneaker. Once you know the formula, you can remix it a dozen ways using what’s already in your closet.

And while you’re at it—grab our Wardrobe Combinations Spreadsheet. It’s full of done-for-you outfit formulas that save you time, energy, and at least one meltdown before brunch.

Ps. we have an entire freebie dedicated to outfit ideas. There are 365 outfit prompts for every day and every occasion of the year! Literally

Because the next time you’re sweating bullets wondering if your outfit makes sense… at least one part of your life will.

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1. Linen Button-Up + Tank + Loose Shorts

Unbutton it, tie it, or toss it over your shoulders—this combo makes you feel styled, not sticky.

Button Down Shirt

$14.99

High Neck Casual Basic Cotton Ribbed Fitted Tank Top

$16.99 $19.99

Drawstring Comfy Elastic Waist Shorts

$27.99

2. Midi Skirt + Fitted Tee + Slides

The skirt adds movement, the tee balances it out, and it works for errands or dinner.

High Waisted Frayed Raw Hem A Line Denim Midi Skirt

$41.99

Double Lined Going Out Basic Tank Top

$25.95 $35.95

Slip On Slingback Heels

$42.73 $44.98

3. Matching Set + Sneakers or Sandals

Zero thinking required. Two pieces, one look. Add jewelry if you’re feeling extra.

Tube Top Bodycon Maxi Skirt

$39.99

Slide Sandals

$29.99 $38.99

4. Flowy Dress + Floppy Hat + Casual Sandals

For days when you want to feel breezy but still a little cool-girl.

Flowy Long Dress

$39.99

Floppy Beach Hat

$25.99 $35.99

Sandals with Memory Foam

$49.90

5. Tank + Pull-On Pants + Woven Tote

A relaxed look that doesn’t look sloppy. Swap the pants for linen or crinkled cotton when it’s really hot.

Tube Top Embroidery Strapless Off Shoulder Top

$27.99

Mid Rise Barrel Jeans

$48.99

Large Woven Tote Bag
$45.89 $53.99

6. Oversized Tee + Biker Shorts + Slides

The “I want to be comfy but still look decent in public” uniform. Add sunnies and call it a look.

Loose Oversized Tops Basic Tee

$19.99

High Waist Biker Shorts
$15.98 $29.99

Sandals with Adjustable Buckle

$18.99 $28.59

7. Wide-Leg Jumpsuit + Crossbody Bag + Sunglasses

A one-and-done outfit that still feels pulled together. Bonus: it’s easy to layer if the weather flips.

Strapless Tube Wide Leg Jumpsuit

$43.98

JW PEI Women's Ashlie Crossbody Bag

$84.15 $99.00

Rectangle Glasses

$14.99 $19.99

8. Romper + Statement Earrings + Flat Sandals

Easy to throw on, cute enough for anything from brunch to the park.

Denim Romper

$42.99

Gold Knot Heart Earrings

$7.66 $12.99

Strap Slides

$39.98 $64.99

9. Cropped Cardigan + High-Waisted Shorts + Tank

You can wear the cardigan buttoned, tossed over your shoulders, or in your bag for AC blasts.

Knit Cropped Cardigan Sweater

$19.40 $29.98

Casual High Waisted Denim Shorts

$39.99

V Neck Tank Top

$16.99

10. Halter Top + Maxi Skirt + Slides

It’s giving summer dinner on the patio. Add a claw clip and a tiny bag and you’re done.

Crop Tops Tie Back Sleeveless Slim Fit Cami Top

$14.99

Wrap Skirt Ankle-Length

$34.99

Square Toe Slip on Slides

$29.99