I need help figuring out what to wear for our engagement picture session. I want to go preppy chic. Everything will be outdoors so I want to stay warm somehow without having to wear an actual coat. I had originally thought of skinny pants with a nice sweater and some booties, but I’m very unoriginal when it comes to outfits! I love wearing dark colors… grays, black, brown… any suggestions? —V, New York

Black skinny pants and a sweater is definitely a great option. But since these are your engagement photos, being a little feminine isn’t a bad idea. A long-sleeve dress with tights and boots will keep you warm but sill let you show off your figure, which is something I’m guessing your fiancé will enjoy.

You say you like dark neutrals so I found a Jarbo Ruched Mini Dress in charcoal. The side ruching is extremely flattering and it would most certainly keep you warm. If you do decide you can do color, eggplant is a great choice. The deep purple is very subdued and looks good with every hair color and on most skin tones. The Velvet Jessamine Dress has similar slimming ruching.

To combat the cold, pair either dress with opaque tights, like Steve Madden’s S-Ftight. Normally, I’d say go for an edgy bootie but you’ll be sending these photos to family members and grandpa might not understand the military trend. Instead, go for a classic knee-high. It will keep you warm and is always in style. Suede photographs softer than leather and the combo of the black hosiery with these Steve Madden Brewster Boots will really elongate the leg.

Some people might say, isn’t this outfit a little boring? But minimalist can be beautiful. Plus, if you add a statement necklace, all the attention will go towards your face. And your joy from being engaged is really what you want to remember and what your family will want to see, anyway. The only bling you want is on your left hand, so instead look for more understated sparkle up top. I love this Samantha House Luster Necklace. The quartz acts like my lucite from my August ttF fashion staples. It adapts to whatever color you’re wearing and it picks up colors from your surrounding, which makes for a really pretty photo.

But the most important thing is to be comfortable in what you’re wearing. When you’re confident with the way you looks it’s pretty hard to take a bad picture. Good luck!

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