What to Wear
(aka: how to not stress over outfits and still look amazing)
Let’s just say it: picking outfits for photos can feel weirdly stressful. Like suddenly your entire closet has betrayed you and you're staring into the void wondering if you've ever actually liked a single piece of clothing you own. Been there.
The good news? You don’t have to dress like you’re heading to a Vogue cover shoot. This isn’t about impressing anyone with your outfit. This is about showing up as you, and celebrating the magic you bring to the table—bedhead, goofy socks, and all.
Now, let’s get this out of the way: I’m not a fashion blogger. My usual wardrobe consists of multiples of the same thing - if I like it I buy it in multiple shades of neutral or pink or blue or green. If it has pockets and makes me feel good I won’t want to take it off... I’m not here to tell you what’s trendy—I probably could - but that’s not important. I’m here to help you feel good and look like yourself.
Style should be a personal thing. Something that reflects exactly who you are.
These little tips below? They’re not rules. Here’s what I can tell you, based on a whole lot of real-life sessions and a sprinkle of trial-and-error. Okay. A lot of trial and error.
Outfits Don’t Make the Magic—You Do
Dressing for Photos:
This one’s perfect for engagement shoots, senior sessions, or branding magic—and yep, it works for cozy at-home family or newborn vibes, too…
A Gentle Nudge, Not a Rulebook Packingfor Your Shoot:
Let’s Talk Outfits & Options
Alright, let’s play dress-up—but in a cool, grown-up, let’s-make-magic kind of way.
Here’s the deal: I highly recommend bringing a few outfit options with you. Why? Because when we’re out adventuring from spot to spot, I’ll help you mix and match based on the vibe of each location. Think of me as your honorary stylist for the day—minus the clipboard and headset.
The goal is to make sure you are the main focus, not a loud pattern or an outfit that feels like it belongs in a different movie. When your clothes match the scenery (and your energy), the photos feel more you and less like you wandered into a catalog shoot by accident.
But here’s the catch—please don’t bring your entire closet.If I have to dig through a mountain of sweaters and "maybe" shirts, we’ll lose precious golden-hour light and, let’s be honest, I’ll probably start panicking about wrinkles. A sweet spot? Around 2-3 bottoms and 3-4 tops per person, plus any fun extras like jackets, flowy dresses, hats, or accessories you love.
Oh, and let’s talk logistics: if we’re shooting in nature or somewhere remote, just know that your changing room may be the backseat of your car or a secluded patch of trees. If that’s a nope for you, no worries—stick with one outfit that you adore and feel amazing in.
Still unsure? Snap a few pics of your outfit options and text them to me! I’m more than happy to help you choose before the big day so you feel totally prepared (and totally fabulous).
Let’s think about where we’re shooting and plan your outfits with that in mind. Trust me—your ankles (and your photos) will thank you.
If we’re hiking off the beaten path, bring shoes with good grip that won’t have you wobbling around like a baby deer. If we’re on a beach, barefoot is the way to go—shoes in sand just look awkward. (Also: heels are usually a no-go unless you’ve got circus-performer-level balance. You’ve been warned.)
If it’s going to be chilly, layer up like you’re heading to a snowy cabin. Wool socks, cozy sweaters, boots that actually keep your toes warm—all that good stuff. If it’s going to be hot, pick outfits that let your skin breathe so you’re not dealing with sweat stains halfway through. Not cute. Not comfy.
Dress for the Adventure,
Not Just the Aesthetic
Her outfit is dressier than his - that’s not necessarily a problem - but had he worn chinos or even jeans with a button-down shirt, this photo would be much more cohesive.
Start with what you already love.
You know those clothes that make you feel like a rockstar on a Tuesday morning? That’s the vibe. If something in your closet makes you feel confident, cozy, or just extra you, bring it. New outfits can be hit or miss—so unless you’re 100% in love with something new, stick with what you already vibe with.
Be comfortable—like, for real.
You’re gonna be moving, laughing, walking, possibly climbing, spinning, or being dramatically dipped by your boo (optional, but fun). If you’re wearing something that digs, pinches, or makes you worried about sitting down—maybe rethink it.
Coordinate, don’t clone.
You do not need to match. In fact, I’d gently beg you not to. Instead, think about choosing colors or styles that complement each other. Think: outfits that look like they’re going to the same party, not wearing the same costume.
Skip the stiff stuff (unless you love it).
If the idea of a collared shirt and shiny shoes makes your partner break into a cold sweat, skip it. Seriously. People are way happier in clothes they don’t feel weird in. A cozy flannel or a soft tee can photograph beautifully if you feel like yourself in it.
Trust your gut.
You know when an outfit feels right. If you try something on and immediately start imagining what it’ll look like in the photos—bingo. That’s your winner. If you put it on and start tugging at it in the mirror? Eh, maybe not.
Wear What You Love, I’ll Bring the Hype
I normally encourage my clients to avoid reds and yellows - unless they have darker hair - olive/darker skin.
These colors are magic here. But honestly—if you roll up in mismatched socks and the world's comfiest hoodie, I’ll still be hyping you like you're walking a Paris runway.
If you show up in your favorite thrift store tee and a smile that won’t quit, I’ll be snapping photos like you’re on the cover of Rolling Stone.
Even if you arrive in clothes that say “laundry day” but your vibe says “iconic,” I’ll be cheering like it’s the season finale of Project Runway.
You could show up in head-to-toe corduroy and Crocs, and I’d still be squealing behind the camera like you invented fashion.
If you walk in wearing your comfort clothes and contagious joy, I promise I’ll treat it like a red carpet moment.
Dress for the Location, Not Just the Look
If we’re hiking at Calvert Cliffs or wandering off-road, you’ll want shoes with good grip (a twisted ankle is not the kind of drama we want). Headed to a sandy beach? Ditch the shoes—barefoot always looks more natural. And just a heads up: heels are almost always a no-go unless you’re some kind of magical heel-walking unicorn.
Cold weather? Layer up! Think cozy sweaters, wool socks, boots, and jackets that keep you warm and cute. On the flip side, if it’s going to be hot, opt for breathable fabrics so you don’t end up with sweat patches making a surprise appearance in your gallery.
Bottom line: the more comfortable you are, the better you’ll feel—and the better your photos will look. Always choose comfort over costume!
When you're planning your outfit, think about where we’ll actually be shooting—and dress for the conditions, not just the aesthetic.
Patterns can be fun… but they can also be total attention hogs.
When it comes to prints, the golden rule is: subtle > loud. Big, bold, busy patterns tend to steal the show—and not in a good way. The goal is for the focus to be on your faces, not your shirt doing the most.
Flannels, though? Always a yes in my book. (But I may be biased—I wear one whenver I get the chance.) Just try not to pair too many patterns together in the same photo. A flannel here, a stripe there, a floral over yonder… suddenly it’s visual chaos and we’re all confused about where to look.
Bonus tip: give your clothes a quick iron or steam before the session. Wrinkles have a sneaky way of becoming the star of the shot, and I’d much rather your smile take center stage.
Let’s Talk Patterns
(and Why Less is Usually More)
This is a great example of color coordinating.
The little guy was rocking a super bold pattern—which, honestly, made my job a bit trickier! Big, busy prints can either blend into the background or battle with it for attention. I ended up hunting for backdrops that wouldn’t turn him into a walking game of hide-and-seek.
Too much of a good thing - in this case is too much.
Unless you all want to match. In which case. I’m here for it.
This isn’t my photo, but let’s talk about what’s happening here: the bright red outfit is super eye-catching—in a way that pulls focus away from the people. While the small pattern itself is totally fine, the bold color is what makes it distracting. Same goes for the baby in yellow—adorable, but those bright tones grab attention first, when we really want the focus to be on faces and connection.
Props? Yes. Corny? No thanks.
The word props gets a bad rap—and honestly, I get it. It might make you think of those staged photo ops with wooden signs that say things like “She said yes!” or chalkboards announcing what someone had for lunch. Cute for some… but not exactly the vibe we’re going for here.
That said, props can actually be awesome—if they’re things you already love or use in real life.
Picture this: a pizza picnic in the trunk of your car, your beat-up old skateboard, a fuzzy dog who thinks they run the show (they do), or a cozy blanket you always keep in your backseat. Maybe it’s your paddleboard, your vintage record player, or a bouquet of grocery store flowers you grabbed on the way because “why not?” energy is the best kind of energy.
Basically, if it feels like you and it adds to the story we’re telling—bring it. If it feels like something a bored craft store display came up with… maybe leave that one behind.
If you’re not sure what counts as a good prop, just shoot me a message! We’ll brainstorm and make sure whatever we include feels natural, fun, and you x 1000.
In-Home Sessions
Engaged Couples - Let’s Get Cozy
(Not Weird, Promise)When it comes to in-home sessions, here’s my honest take: the more skin showing, the better. Not like, scandalous… just real-life comfortable. Think less “glam photo shoot” and more “Sunday morning, no plans, no pants.”
We want these photos to feel intimate and relaxed, like we’re just capturing a slice of your actual life—not like you’re bundled up for a snowstorm in your own living room.
Tank tops, off-the-shoulder sweaters, bralettes, soft tees, cozy joggers, jeans, boxers—yes, yes, yes. Layers you can mix and match, pieces that fall just right, things that make you feel like your natural, at-home self. A big cozy sweater and undies? Iconic. Your partner shirtless and making coffee? Chef’s kiss.
And just to clarify—I pinky swear I’m not a creep. This is all about comfort, vulnerability, and real connection. You’re not dressing for an audience—you’re dressing like you forgot I was there (in the best way possible).
So bring those lived-in layers, let the light hit your shoulders, and let’s make some honest-to-goodness magic.
Family Sessions:
Keep It Cozy & Real
For in-home family sessions, my biggest tip? Keep things comfy and low-key. We’re not going for a styled magazine shoot—we’re capturing real-life magic. The kind with bedhead, giggles, snack breaks, and couch snuggles.
Think about how you actually dress when you’re lounging around together: soft tees, cozy knits, leggings, relaxed joggers, bare feet, and maybe a kid or two in pajamas that don’t match. That’s the energy we’re after.
For Anyone:
Want to Dress It Up a Bit?
Let’s Keep It NaturalIf you’re someone who loves a good excuse to dress up—amazing! You can absolutely bring a little extra polish to your in-home session while still keeping things soft and relaxed.
Think natural, effortless beauty: loose, flowing dresses that move with you, breezy fabrics, and soft tones that photograph like a dream. Hair down and wild or in a simple braid, a little bit of makeup if that’s your thing (but keep it light—your everyday beautiful is more than enough), and barefoot all the way.
The goal here isn’t to look “done”—it’s to look like you, just a touch elevated. Picture the kind of outfit you’d wear if your home life was being turned into a cozy, dreamy storybook.
Whether you're curled up in your reading nook or dancing barefoot in the living room, I want you to feel like yourself—but with a little sprinkle of magic.
Hair & Makeup
Let’s talk beauty prep, shall we?People ask me all the time if they should get their hair and makeup done professionally for their session. And my answer is: only if you want to.
Seriously. Do whatever makes you feel like your most confident, radiant self. If that’s a blowout and a full beat? Go for it. If that’s your go-to messy bun and a dab of tinted lip balm? Love that for you.
Personally? I like looking like myself in photos—laugh lines, wild curls, and all. I’ve seen too many folks show up with their faces airbrushed within an inch of their lives and hair so shellacked it could survive a hurricane. And by the time we’re five minutes in, they’re pulling out bobby pins like they’re defusing a bomb and asking for a tissue to tone it all down.
So here’s the rule: if pro glam makes you feel like a rockstar, go for it. But if it makes you feel like someone else entirely? Skip it. The camera loves confidence, not contour.
Timing tip: If you are getting your glam on, make sure you’re all done at least an hour before you need to leave. We don’t want to be racing the sunset because someone was still waiting for their winged liner to dry.
Tan tip: Planning on a spray tan? Choose the natural, airbrushed kind—the one that says “I just got back from a relaxing weekend in the mountains” rather than “I lost a bet at a spray tan salon.” Subtle glow > surprise pumpkin.
Need more visual inspo?
If you're feeling stuck or just want a little visual inspiration, I’ve put together a few Pinterest boards to help get the wheels turning. Whether you're leaning toward cozy neutrals, playful textures, or something a little more whimsical, there's a board to spark ideas and help you feel more confident choosing what to wear. No pressure to copy anything exactly—it's just there as a jumping-off point if your brain is yelling “I have nothing to wear!” (We’ve all been there.)
Our Pinterest is filled with all kinds of visual goodness. Find us at Olea + Co Photography
And if you’re more of a “just tell me what to wear and make it easy” kind of person (same),send me photos of what’s in your closet and I will happily help you figure this all out - I promise it’s not that hard. If you’ve got your heart set on something new. I’ve got you covered there too. I have put together a few blog posts with simple, photo-friendly outfit ideas you can grab right off Amazon (or your closet). No mall meltdowns required—just a few clicks and cute, comfy outfits delivered straight to your door.
Easy peasy. You can check it out my What to Wear Client Resources when you're ready to start adding to cart!
And if it helps, I also have a style closet clients can borrow from. - Dresses, outfits for the littles, and cozy sweaters etc.