I’m constantly inspired by women who make style look effortless. For me, my friend Jasmin McDonald (@jasmcdonald) is one of those rare muses whose wardrobe feels like it could run your 9–5 and have you sipping martinis by 7 pm. When she stepped into the studio for our session, she brought three distinct headshot outfits that told a refined, confident story.

For those who religiously follow Jasmine’s Workwear Wednesday series on IG Stories (me!), you’ll know these outfits are just a typical Wednesday for her.

What struck me most is how seamlessly they bridge the world of corporate power dressing and editorial-level styling. These aren’t “photoshoot only” looks — they’re the wardrobe you want to own, wear, and rewear.

Below, I break down each outfit, why it works so well, and how you can interpret this for your own personal branding photos— especially when you’re wondering what to wear for headshots, branding photo outfits, and day-to-night wardrobe magic.

Read More: Take a peek at this interview with Style Me Tay on how to select killer headshot outfits (you’ll want to cross‑reference this).

Outfit 1: Oversized Shirt Dress + Knee High Boots

Why it works for branding photos + real life

• Effortless movement. The oversized cut gives you room to breathe, pose, and shift. You don’t feel constrained.
• Statement boots anchor the look. The maroon suede adds texture, personality, and a luxe edge, while still reading polished.
• Versatility in contrast. The shirt dress leans soft and fluid; the boots push it into a more editorial, fashion-forward realm.
• Styling continuity. The low bun and gold accessories keep it refined without competing with the headshot outfit’s silhouette.

How to wear headshot outfits beyond the studio

• Swap in knee-high leather boots in black or tan for daytime office wear.
• Throw on a tailored belt to cinch at the waist for a more structured silhouette.
• For evening: throw on a sharp blazer or moto jacket, add a cute bag and you’re ready for dinner or drinks.

Entrepreneurs This Outfit Works For

This look is a dream for stylists, hair and makeup artists, boutique owners, or any woman in a creative but client-facing industry. The oversized shirt dress reads cool and fashion-forward, while the maroon suede boots add a luxe punch of personality. This headshot outfit is for women who don’t mind turning heads in the best way. Your branding photos will reflect your eye for detail, drama, and elevated trendiness.

Think of it as: editorial energy meets confident entrepreneur.

Look 2: The Capsule Wardrobe Power Combo

Why it works for branding photos + real life

• Clean lines, strong contrast. The black + white color pairing is timeless! The silk tank keeps things elevated and soft.
• Unexpected denim. Instead of going full suit, she anchors it with raw-edge jeans for a casual but sophisticated look.
• Gold detail elevates simplicity. The belt and jewelry give polish without shouting “look-at-me.”
• Photoshoot potential. The outfit photographs beautifully: the structure of the blazer, the drape of the silk, the shape of the jeans.

Read More: A Small Business Owner’s Guide to Branding Photography Pricing

How To Wear It Beyond The Studio

• Office: Leave it as is (blazer on, hair down or tucked behind ear, minimal jewelry)
• Branding shoot: Roll blazer sleeves, untuck one side of the tank, play with angles
• Happy hour: Ditch the blazer (or slide it off your shoulder), add a bold lip, throw your hair up, and maybe swap heels for strappy sandals

Women Creatives This Outfit Works For

This is a great go-to outfit for branding photographers, creative consultants, online business coaches, and event planners who need to walk the line between approachability, professionalism, and authority. It’s clean, classic, and camera-ready — the kind of look that’s as fitting for a sales call or speaking engagement as it is for your website’s about page.

If you’re wondering what to wear for a professional headshot or looking for branding photography packages that elevate your online presence, this headshot outfits guide is proof that you don’t need complicated clothes to make a powerful impression.

Look 3: Elevated Denim on Denim

In her own words, this outfit is giving “psych thriller author” vibes. I’m absolutely obsessed with the unexpected tension in this combo — it feels literary, moody, confident, and comfortable.

Why it works for branding photos + real life

• Layered texture play. The denim shirt softens the blazer. The plaid brings visual interest and structure.
• Contrasting scales. A casual top (denim) + more formal blazer = unexpected balance.
• Slingbacks seal the deal. They elevate the whole thing from jeans + blazer to editorial styling.
• Intentional tension. The look says: “I’m ready for my closeup and to kick back afterwards”

How To Style This Outfit Beyond The Studio

• Swap the jeans for a leather skirt or slim black pants for evening.
• Wear the blazer over a silk slip dress as an accent for mixed-fabric layering.
• For a more corporate twist: tuck the denim shirt, layer a waist belt, and pair with a large leather tote.

Creative Solopreneurs This Outfit Works For

This third look speaks to authors, designers, event creatives, photographers, and artists who want their photos to feel elevated but still grounded in who they really are. The layered soft denim and clean plaid texture create an intentional (no try-hard!) vibe.

If you want to showcase your creative process over perfection, this outfit offers just the right amount of structure with the softness of well-loved pieces.

Ideal for women who ask: “Can I look professional and still feel like me in headshots?”

Short answer: Yep! This is it.

Read More: How to Use Your Personal Branding Photos on Social Media

Why Jasmin’s Style Feels Rewearable & Timeless

The “day to night” craze back in the early 2000s had us in a chokehold; every magazine and fashion blog convinced us our closets needed to be full of workwear you could party in. Now that we have the luxury of hindsight, I think we can all agree that “just add heels and a clutch” was not the helpful style advice it was cracked up to be.

But here’s what Jasmin’s style reminds us: the best transitional headshot outfits are the ones designed to be versatile from the start — not ones you force into two different lives.

• She doesn’t “dress up” for the shoot — she brought real clothes she lives in.
• Every piece is rewearable, not exclusive to the photoshoot.
• She blends structure + softness, edge + polish. That tension is what gives longevity.
• She layers smartly. You can push each look further or pull it back easily.

That’s where the real benefit lies: you don’t need special “headshot outfits” you’ll never see again. If you build out a wardrobe of well-fitting pieces with strong lines, elevated basics, and a handful of statement shoes/jewelry, you can style smarter, shoot better, and wear more.

Tips for Styling Your Branding Session (and Beyond)

1. Stick to your palette. Choose colors and tones that flatter your skin tone and photograph well.
2. Play with proportions. Oversized top + tailored bottom, or slim top + relaxed pants — variety is your friend.
3. Mix textures. Silk, suede, tweed, structured knits — they add dimension in still images.
4. Don’t over‑theme. Let your personality shine, not dominate. A blazer is timeless; neon fringe is not (unless that’s your brand!).
5. Bring extras. A blazer you love, a hat, a statement shoe — we love options.
6. Comfort = confidence. If you feel awkward, it will show.

When folks ask me “what to wear for headshots women / what to wear for professional headshots”, I always come back to these principles: build a capsule you love, layer with intention, and bring bold shoes, jewelry, or accessories for personality.

If you’re styled and ready to book your next headshot or personal branding session, let’s chat here!