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Hi, I’m Steph.
entrepreneur, realistic outfit enthusiast, wellness advocate, & your newest bff for living wholly while on a budget.

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What to Wear with Shorts: 10 Summer Shorts Outfits I’ll Be Wearing on Repeat

Summer is here, and you know what that means—it’s shorts outfits season! Whether I’m running errands, headed to brunch, or getting dressed up (ish) for a dinner out, I find myself reaching for shorts almost every day.

But styling shorts can be tricky! You don’t want to look like you’re headed to a high school gym class, and you definitely don’t want to feel underdressed. I rounded up 10 of my recent favorite outfits from LTK so you can shop them if you want to recreate the look, or just grab a little inspo for mixing up your own closet. Lots of these pieces are neutral or super wearable across seasons, and I tried to include shorts outfits for every mood—casual, girly, edgy, and in between.

Just a note: this blog post contains affiliate links, which means that at no additional cost to you if you purchase through these links I make a small commission.

1. Varsity Jacket + Gingham Shorts

What to Wear with Shorts: 10 Summer Shorts Outfits I’ll Be Wearing on Repeat | Steph Schutt

This look is so me right now—my go-to red and white gingham shorts paired with a white tank, a varsity jacket, and my favorite brown cowboy boots. I’ve been loving this combo for running around town or heading out on a casual weekend with the family. It feels relaxed but still pulled together. These boots are also surprisingly comfy for all-day wear.

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2. Graphic Tee + Rain Boots (Yes, really)

What to Wear with Shorts: 10 Summer Shorts Outfits I’ll Be Wearing on Repeat | Steph Schutt

Okay, hear me out on this one—I threw on a vintage horse graphic sweatshirt over light-wash shorts and purple rain boots, and honestly, it’s kind of my dream outfit for a rainy day. The oversized fit on top balances out the shorts, and the boots add a fun little pop of color.

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Also, if you’re a mama or just always chasing someone around (hello, real life), rain boots that are cute and functional are a win.

3. Button-Up + White Shorts

What to Wear with Shorts: 10 Summer Shorts Outfits I’ll Be Wearing on Repeat 
| Steph Schutt

This one feels a little more polished—great for brunch or a casual meeting. I wore a striped button-down with my white denim shorts and (surprise!) the same cowboy boots from earlier. This outfit kind of walks the line between preppy and country, which I love.

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You could easily swap the boots for sandals or sneakers if you want a different vibe.

4. Boho Vibes with Denim and Crochet

What to Wear with Shorts: 10 Summer Shorts Outfits I’ll Be Wearing on Repeat | Steph Schutt

This outfit just feels like summer. I paired my favorite frayed denim shorts with a white crochet tank and my go-to cowboy boots. It’s one of those combos that looks like you tried harder than you did (my favorite kind of outfit). I’d wear this for a weekend away, outdoor concert, or casual hangout with friends.

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5. Pink Ruffles + Denim

What to Wear with Shorts: 10 Summer Shorts Outfits I’ll Be Wearing on Repeat | Steph Schutt

This one feels sweet and feminine without being too precious. The pink ruffled blouse is lightweight and flowy, and I paired it with pale blue denim shorts and black platform sandals. I could wear this to the park or on a picnic to feel breezy and cute.

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6. Minimal and Neutral

What to Wear with Shorts: 10 Summer Shorts Outfits I’ll Be Wearing on Repeat | Steph Schutt

This outfit is basically what I throw on when I want to look like I tried without actually trying. A white smocked top, light denim shorts, and brown boots again. The smocking adds a little structure, and the brown boots keep it grounded and classic. I usually toss on a simple gold necklace or some hoop earrings and call it a day.

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7. Beachy Yellow + Woven Sandals

What to Wear with Shorts: 10 Summer Shorts Outfits I’ll Be Wearing on Repeat | Steph Schutt

This one’s giving summer-in-costa-rica energy. Yellow crop top, light blue shorts, and woven sandals. I added a straw hat when I wore this on vacation, but you could totally wear this for a beach day, lake trip, coffee run, or just a hot Saturday of errands.

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8. Black-and-White Stripes + Boho Slides

What to Wear with Shorts: 10 Summer Shorts Outfits I’ll Be Wearing on Repeat | Steph Schutt

This look is one of my go-to outfits when I want something that feels timeless but still a little fun. I paired this classic black-and-white striped long sleeve tee with my favorite light-wash denim shorts—it’s such an easy combo that works for just about anything on my calendar. I finished it off with these tan slides for a hint of boho flair.

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9. Road Trip Retro

What to Wear with Shorts: 10 Summer Shorts Outfits I’ll Be Wearing on Repeat | Steph Schutt

This one makes me want to hop in the car and drive somewhere with no plan. I wore a vintage-style, oversized Ford Bronco tee with these sapphire blue shorts and black boots—classic, easy, and just a little nostalgic.

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10. Feminine florals with a western flair

What to Wear with Shorts: 10 Summer Shorts Outfits I’ll Be Wearing on Repeat | Steph Schutt

I love the way this outfit blends soft, feminine details with a little western flair. This floral blouse has the prettiest pattern and pairs so well with light-wash denim shorts for an easy summer look. I added my white cowboy boots to give it a fun, bold twist—and I honestly think they make the whole outfit pop!

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A Few Tips for Wearing Shorts Outfits (That I Actually Follow)

  • Go for comfort first. If you’re tugging on them all day, they’re not worth it. I always go for soft denim or anything with a little stretch. Here’s a round-up with 5 of my favorites that I wear all summer long.
  • Don’t skip accessories. A simple bag, statement sunglasses, or cute sandals can take a basic outfit up a notch.
  • Stick to a palette. I tend to go for neutrals, with one color pop if I’m feeling it. That way everything mixes and matches easily.

That’s the full shorts outfits roundup for now! I’ll keep adding to LTK as I wear more summer outfits, but hopefully this gives you a few ideas to play with. Whether you’re packing for a trip, hanging with your kids, or just trying to figure out what to wear when it’s 87 degrees before noon—shorts are a forever staple in my book.

Let me know which outfit is your fav!

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