What to Wear for a Winter Engagement Session: Wisconsin Edition

Outfit Ideas That Feel Comfortable, Natural, and Photograph Beautifully

Winter in Wisconsin has a charm all its own: snow-covered trees, cozy textures, and soft, flattering light you just can’t recreate in any other season. One of the most common questions I hear from couples planning a winter engagement session is:

“We’re not super dressy people… but we still want to look good. What should we wear?”

Good news… You don’t need to feel stiff, overly formal, or like you’re playing dress-up to look amazing in your engagement photos. Winter is actually one of the best seasons to lean into comfortable, elevated outfits that photograph beautifully while still feeling like you.

Below are my go-to winter engagement outfit ideas, color suggestions, and styling tips specifically for Wisconsin winters.

Start with Comfort (It Always Shows in Photos)

If you’re uncomfortable, it will show, especially in winter. The key is choosing outfits that allow you to move, cuddle in close, and stay warm without distraction.

Think:

• Layers instead of bulky coats

• Soft fabrics with texture

• Outfits you’d actually wear on a nice winter date

When you’re comfortable, you relax — and that’s when the real moments happen.

Best Colors to Wear for Winter Engagement Photos

Winter landscapes tend to be neutral — whites, grays, evergreens, and muted skies. This gives you a perfect backdrop to wear colors that feel rich and intentional without overpowering the scene.

Colors That Photograph Exceptionally Well:

• Cream, ivory, oatmeal

• Camel, tan, warm brown

• Deep green or forest

• Navy

• Burgundy or wine

• Charcoal gray

These tones add warmth and depth while still feeling timeless.

What to Avoid:

• Neon or overly bright colors

• Large logos or graphics

• Busy patterns that pull attention away from your connection

• Stark black on both partners (can feel heavy in winter light)

Outfit Ideas for Couples Who Aren’t “Dressy”

For Her

You don’t need a formal dress to look incredible in winter.

Great options include:

• A midi or sweater dress paired with tall boots

• A soft knit sweater tucked into high-waisted pants

• A neutral coat (camel, cream, or gray) layered over your outfit

• Textures like wool, cashmere, or ribbed knits

Tip: Movement matters. Pieces that flow slightly photograph better than stiff fabrics.

For Him

Polished doesn’t mean uncomfortable.

Try:

• A crewneck or quarter-zip sweater over a collared shirt

• A Henley or textured knit for a more relaxed look

• Dark denim or tailored pants

• Leather boots or clean winter shoes

Layers add dimension and give you flexibility if we’re moving between indoor and outdoor locations.

Coordinating Without Matching

Instead of wearing the same color, aim to complement each other.

For example:

• One partner in a lighter neutral, the other in a deeper tone

• One textured piece (knit, wool), one smoother fabric

• Similar warmth levels (don’t pair a summer-weight outfit with a heavy coat)

The goal is balance — not identical outfits.

Winter Accessories That Actually Help Your Photos

Accessories can elevate your look and keep you warm:

• Scarves in soft neutrals

• Knit beanies (minimal branding)

• Gloves that match your coat or boots

Pro tip: Choose accessories you’re okay taking on and off. We can mix up looks quickly without a full outfit change.

Trust the Process (and myself as your photographer)

Winter engagement sessions are all about leaning into the season… cozy moments, close connection, and natural interactions. You don’t need to overdress or feel like someone you’re not.

When you choose outfits that:

• Fit well

• Feel comfortable

• Complement the winter environment

…your photos will feel authentic, elevated, and timeless.

If you’re ever unsure, I’m always happy to review outfit options or help you narrow things down. Styling is part of the experience — and I want you to feel confident walking into your session.

Looking for More Engagement Session Tips?

You can find additional resources, galleries, and session information at by clicking here.

Winter in Wisconsin is beautiful… and one of my favorite seasons to photography… let’s make sure your engagement photos reflect that.