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What to Wear for your Colorado Winter Engagement Session


Are you lost or overthinking what you should wear for your winter engagement session?

This is a topic I have actually avoided blogging about for years. But one of my clients Lauren has won and finally convinced me to do it. I definently have thought about it many times and have a lot to say, so the reason I have avoided it may not be what you think. I think this is one of the most overthought topics for clients. So I am not going to be super specific with pinterest boards and laid out outfits for you... I will get to the why here in a minute. But starting now, I want you to see this all in a brand new way.

When thinking about a Colorado Engagement Session in the winter, there are a few key factors to getting your wardrobe right.



Let's start with Authenticity. My number 1 thing I tell my clients when planning their engagement session is to remain authentic. To themselves, to their specific adventure, to their location. Just a bit elevated. So if you are doing a hiking engagement session with me, I def don't expect you to show up with a messy bun and a sports bra. Obviously I still want you to look nice. BUT authenticity is so important for the overall feel of the photos. And we will likely be doing the activities for at least part of the session, so it is key that you are dressed appropriately for it. So if we are hiking in, we will likely stop along the way to take photos... find the balance in between the clothes that make sense for hiking and something cute. What would you actually wear to hike I’m the winter? Probably warm clothes and good shoes. You can make practical and authentic clothes cute by adding accessories like a cute new beanie, a scarf, an outdoorsy backpack. Make it real and true to what you are doing... usually if your hair is done and your makeup is on, that lends itself to making it more ‘photo worthy’ than the usual messy bun and clean face. Add in some earrings and you are set. The session isn’t about the clothes, it’s about you but they should lend themselves to making your photos more believable and true to who you are and true to the situation you are in. A HUGE part of my personal style really has to do with the feel of photos. Of course I want you to look great, but I want you to FEEL great. I want people... even complete strangers to FEEL the joy in your adventure and the love between you. It should be a feeling that I can't shake, that you can't shake and anyone (again even people who don't know you) who sees your photos can't shake. But the clothing needs to accentuate your story, the story of the day and who you are as a couple to be believable and to allow us to get to that emotional feeling in the photo. If your clothes don’t look like they belong with what you are doing, it will lead to an internal skepticism of the entire photos and no one will get to the point of feeling and believing your photos. So, if you are doing ski/snowboard photos.... you are going to look silly in anything BUT your gear. (Bonus tip, wear a cute long sleeve under your coat in a color that compliments your board/skis and/or coat/pants.... we will take off some layers to shed some top pounds, but still look authentic, think spring skiing!) Bring your goggles, your board, coat, pants, hat, all of it. I will 'edit' (take something out) if it is too much. If you are out in the woods even if it's just playing around, a cute sweater and hat are perfect (if you don’t want to wear a hat you don’t need to, it’s a suggestion to accessorize but don’t overdo it, let your hair down and just be you!) ... guys, flannels or pullovers are perfect. But you will look out of place if you wear a blouse or a dress shirt... if it’s a business formal or even a bit more business casual look, skip it. Make sure it is authentic for the season too... no sundresses or short sleeves guys. It just looks out of place. There are instances when lacy or boho dresses work... just think about the weight of the fabrics. If it’s super light and airy, it will look out of place in the winter. ALWAYS go for authenticity... except when going super glam. There is always something beautiful about a gown out in the snow. But don't go halfway here. If you are going glam, go all in. Seriously make it as elegant and upscale as you can. You have to make it look completely purposeful. I’m sure you’ve all seen influencers in these gorgeous gowns or suits in places that don’t necessarily make sense, but that is on purpose. So if you are doing it, go all out and MAKE it obvious, even a bit outrageous! But again, if it isn't you... don't do it. Everyone will know it's just not your style. Staying true to yourself but looking like your best self and more importantly feeling like your best self is the most important aspect... which brings me to our next topic.

Pick what YOU feel best in. This is the number one tip I tell my clients... and can also be one of the most ignored tips that I give. DO NOT PICK SOMETHING THAT YOU DON'T FEEL CONFIDENT IN. Do not squeeze yourself into something too small, or ill fitting... and if you are ordering something online, MAKE SURE YOU GET IT IN TIME TO MAKE SURE IT FITS IN A WAY YOU FEEL GOOD ABOUT. Also, this is the other reason I encourage people to bring at least 2 outfits (More to be safe!) This way if you aren't feeling good in the moment about it or you aren't sure how it will photograph, you have backup options. But I think we all know that we have at least one outfit that we feel great in. Like our true selves. Maybe it's your color, maybe the jeans make your butt look good or you have happy memories attached to a certain shirt. If it fits the authenticity bill, bring it. Again, if it's your little black dress for a night out on the town, bringing it out to the woods in two feet of snow probably isn't your best move. And if you were going to wear it for a job interview, it’s probably not going to fit the authenticity criteria. If you feel like you want something new and fresh that no one has seen, go for it. But again, you need to get it in advance to make sure it fits you well and if not, that you would have enough time to figure something else out. Make sure it is something you can MOVE in too! I am a photographer who makes people move around a lot which can prove a bit difficult or can cause a little insecurity when things aren't staying where they are supposed to! And if there is something that bothers you, point it out to be at the beginning of the session and then forget about it! I will take care of it!!! If you do not feel good about yourself, it will show in the photos. I want you to come into your engagement session feeling like hot shit. I know it sounds silly, but I am DEAD serious. And if you aren't a super confident person, I will help with that... but I will need a little bit of your help. Fake it till you make it! ;)

Now, into the more detailed tips... * LAYER - It will likely be kinda chilly out so this way you will be more comfortable and we can make the same outfit look different in various shots. * TEXTURES - Bring in different textures to add depth to your photos, this can be a sweater, a scarf, a hat... even jewelry brings in new elements and textures. Velvet is also a favorite winter texture! * ENHANCE THE AUTHENTIC - Obviously, like I went on and on about for a few paragraphs, authenticity is super important to me. BUT you should still accessorize it and enhance it. Get yourself a cute new tee to layer under a flannel or jacket. It would actually look REALLY cute to have a long sleeve 'Fiance' Tee that goes with your snowboarding/ski coat... that way we can unzip it and show off this awesome statement piece. Add in accessories like glam earrings or cute snow boots. Bring beanies, bring wide brimmed hats, bring scarves.... But just enhance the authentic. * ADD IN PROPS - Bring a blanket big enough for both of you that looks good with your outfits. (not too patterned if you can get it, faux fur or knit looks great here!) Bring yourself a thermos with something to warm you up. Don't forget your actual winter props like skis and boards, sleds, snowshoes, skates, hockey sticks. And I'm sure some of you have seen our truck/jeep/car photos.... these are super popular with the guys... but I also have had some awesome off roading women who love them too! So if you have an awesome truck/Jeep/car... make sure it’s photo ready too! But a little dirt doesn’t hurt. *BRING YOUR DOG - This does depend on the location you choose and if they enjoy snow. But I love dogs! If their collar is a neon or a color that clashes with what you are wearing, you can a) take it off for a few photos if they will listen well enough or b) a cute bandana that hides it if they need to stay leashed. I do recommend bringing a blanket if you have a pup. While many of them love playing in the snow, they won’t generally sit in it... and the blanket can also be helpful since I will likely make you get down on their level. Try to remember a lint brush too if they have light colored fur or are prone to shedding. *AVOID - First off, DO NOT COMPLETELY shun any of these things for the session. These guidelines can be nixed if it applies to any of the criteria above. DO NOT count out a piece of clothing because of it's color or any of these things if it falls into any of the other criteria, but you can always bring it and ask If you aren’t sure. And I'll give examples of when not to worry. Neon Colors - These can leave color casts on your face or your significant other's face which isn't the most attractive. Exception: When it is your ski coat, goggles, etc... then bring on the neon! Black - Black doesn't photograph well in the snow. It's super harsh and washes you out in a particularly light and bright setting. Exception: Ski/Snow Gear, Small bits of black... like black pants are great... but all black outfit=no. One last exception is the glam side. If you want a glam look, black is as classic as you can get. Just don’t go too Johnny Cash here, too much black while slimming can actually be unattractive in such a bright setting. Things with large logos or sayings - Stay away from anything branded. You aren't in a clothing catalog. You want the focus to be on you, not the giant brand name stamped on your shirt. Exceptions: Pretty much everything if it is right. Again if it comes down to your authentic outfit.... like wearing a Bauer jacket while playing pond hockey together isn't a bad thing... neither is a burton Jacket or a Carhartt beanie. Words (here’s some contradicting advice for you) can also be gimmicky... unless it says something pertaining to the photos like a cute adventure-y shirt or something that again says Fiance or similar. Go bold with these words though... if they are too small or not bold enough, you won’t see them. SHOES - This is a HARD one for many people. Make sure the shoes are realistic for where we are going. Snow boots are a fantastic idea. You can bring other shoes, but often times I'm going to ask you to get in deeper snow... so please approach this with caution. Dress shoes and heels are appropriate for the glam ones, just be aware that your feet may be ice blocks for a min. Bring an extra pair of dry shoes and socks for the ride home (pants also may be good if the cuffs are wet from snow. RENT!- Yes, you can rent clothing items for your session from places like Rent the Runway. They EVEN have really cute coats and jackets and it's much cheaper than buying a new one for the session! They have jewelry and tons of other accessories too. SUNGLASSES - please avoid wearing sunglasses while you are outside just before and during your engagement photos. I know it's hard to do... my husband is one of the people who can't leave the house without them. BUT it actually makes you squint so much more and your eyes have a hard time adjusting. So try your best to leave them off beforehand. Coats - Don't worry about coats being too bulky.... they are supposed to be. They actually do add to the authenticity of your session as well... We will have them on and off (if planned that way). But again, if you are in the forest in a foot of snow, people are going to expect you to be wearing more than a tshirt.

My FINAL piece of advice. DO NOT OVERTHINK THE CLOTHES. The clothes can definently elevate your photos... but what is going to be most important is your attitude. So pick something that you feel AMAZING in, make sure it fits authentically with your personalities, the location and the activity/adventure you are doing. And if alllllll else fails (my clients) please text me a picture and we can discuss it together... or you can bring it and we can make the final decision then.



Clothing suggestions for specific areas & activities



Vail Engagement Session

Outfit 1: Ski/Snowboarding Layer with a cute top for some slimming photos sans coat/extra layers goggles/beanie coat/snow pants

good boots

Outfit 2: Romantic Village Photos Sweaters or Button down (men) Peacoat or other coat leggings and boots, OR optional glam look with: gown + suit/tux dress shoes jewelry and accessories shawl/shrug Colorado Cabin Engagement Session

Outfit 1: Outside/Forest Photos Warm clothes including: Coats Beanies Leggings/Jeans/Snow Pants Coffee/Hot Chocolate/ Mulled Wine and mugs! A blanket to cozy up with

Outfit 2: Inside/Cozy Photos

As silly as it sounds, cozy pjs or cute sweats Literally just think cozy for these! Rocky Mountain National Park Winter Hiking Session

(bring a backpack and crampons!)

Outfit 1: Outside/Forest Photos Coats Beanies Warm Pants Maybe a treat for the top like a picnic or warm drinks in a thermos Something to cover your face if it is windy! We don't want your face to be red and chapped!

Outfit 2: Casual Winter Wear or Glam Bring in something more romantic and cute but still casual for the highlight of the hike or Bring a glamorous gown and suit! Colorado Springs Engagement Session - Woodland Park Engagement Session

Outfit 1: If It's Snowing or Really Cold Warm clothes including: Coats Beanies Leggings/Jeans/Snow Pants Coffee/Hot Chocolate/ Mulled Wine and mugs! A blanket to cozy up with.

Outfit 2: If it's a gorgeous day... Flannel and Sweaters A cute jacket (instead of a coat) Your dog!

Keystone Pond Hockey Engagement Photos (or similar locations) Outfit 1: Hockey Skating Photos Hockey Skates Beanies Sweater/Coat Leggings (guys either jeans/pants or athletic sweats) Hockey Sticks Outfit 1 Alt: Romantic Keystone Skating Engagement Photos (non hockey) Leggings/dressier pants Peacoats or Overcoats Skates (or location with rentals) Something warm to drink after! Broadmoor Winter Engagement Photos or Downtown Winter Engagement Photos Outfit 1: Formal Attire Tights Skirt and blouse or dress Heels Peacoat, overcoat, shawl or shrug. Mens semi formal - dress pants, button down, sweater and dress shoes Outfit 2: Glam Gown Suit/Tux Shawl and Overcoat Dress shoes/heels Champagne to (shake up and then) pop!

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Callie Riesling Photography is a Colorado Wedding Photographer

based in Colorado.  We specialize in mountain weddings + 

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