Style Guide for Men: What to Wear to Your Engagement Session


Last week I shared some links to dresses/outfits and some tips for ladies on what to wear to an engagement session. This week, I’m talking to the guys! That’s right, men… the focus is on you for once! 🙂 If you’ve ever wondered, as a guy, what to wear to an engagement session, look no further!

I’m going to clear the air and let you know that yes, I am trying to do your girl a favor here. 😉 But I’m also here to do you a favor! If you follow these styling tips, you won’t have to worry about holding up 6 different ties until your woman picks one, or risk showing up in something that makes her give you the “we’ll talk about this later” look. (Ladies, admit it… you know the one.) I’m here to make sure you show up to your session in something that will lead to some major brownie points with your lady. So let’s dive in:

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For guys, I find it’s best to provide a style guide in the form of do’s and don’ts. Keep it simple, right? So, men…


  • …show up in that pair of sneakers you wear everywhere. You know, the tired ones that are super comfy and “match” everything you own? Let’s leave them behind just for today.
  • …wear an old T-shirt. For the casual outfit, I don’t mind a solid-colored cotton V-neck, but make sure there are no graphics from your old wrestling team on it. If you’re going the T-shirt route, stick to basics: white, blue, or red, V-neck or crew-neck, and properly fitted (avoid baggy ANYTHING!) Actually, let’s discuss that next…
  • …wear baggy clothes. Shirts should hang only just below the belt, if not tucked in. Sleeves shouldn’t fit two of your biceps in them; and if you wear long sleeves, they should stop at or right after your wrist-bone. Jeans/pants need to be the right length too.
  • …forget to iron. My camera will find those wrinkles, so pay a little extra attention to your outfit in this area.


  • …dress up for your girl. You might be the kind of guy that owns 3 T-shirts and wears the same dusty pair of jeans every day. But this is a special occasion for you and your sweetheart. Ladies love when their man dresses up for them, and this session provides the perfect opportunity to show her how proud you are to have her on your [well-dressed] arm. Don’t turn your nose up immediately to wearing the outfits I’m about to suggest. Keep an open mind; and remember that if this isn’t typically your thing, you’re doing it for her.
  • …wear a belt. The quickest way to dress up any outfit is by throwing on a nice leather belt! Avoid worn out belts or anything with a large buckle. And tuck in that shirt 😉 Though, casual outfits I’m a little more lenient on.
  • …wear a collared shirt. Even for your casual outfit, this is a good move. Opt for a polo or short-sleeved button down for spring/summer casual; a collared flannel or nice sweater for fall/winter casual. For your formal outfit, COLLARS. ARE. A. MUST. Dress shirts are your safest bet!
  • …shower. Ok, stop laughing. I mean it. I can’t tell you how many engagement photos I see and I can just tell the guy did not do a whole lot of “maintenance” work beforehand. Shower, shave, get that haircut she’s been reminding you about — heck, even put on some cologne! You’re going to be posing with your girl, so you’ll want to smell good for her (treat the session like a date). Plus, I’m convinced that when a guy smells good, he poses so much better because his confidence goes way up — guys that smell good know how to look good.
  • …try out some accessories/layering! Maybe throw on a tie. Just make sure it doesn’t have any bold or distracting patterns to it. Simple and sleek is a safe bet (opt for solid colors that compliment your outfit). Wear a watch or a pocket square (optional). If it’s a fall/winter day, why not try wearing another layer? I love the “sweater with a popped collared shirt underneath” look, or throwing a jacket or sports coat over your dress shirt.
  • …ask for her opinion. When in doubt, let her help. 🙂

Ok, now for my visual learners… below are three looks for each outfit (formal and casual) that I love!! Feel free to use these as inspiration. (Disclaimer: Photos are NOT my own… found on Pinterest. For more inspiration, view my formal and casual Pinterest boards to give more inspiration on what to wear to your engagement session!)



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