Men’s Fall/Winter Outfit Inspiration

It’s officially November, and that means that sweater weather and fall family sessions are in full swing! Today I thought I’d touch upon a topic that is sometimes woefully neglected…*drumroll* what to wear for your fall/winter portrait session, guys’ edition!! That’s right, dads and husbands, the spotlight is solely on you this week! 🙂 My goal is to help you look and feel your best, with timeless styles that will still look great years from now.

I’ve put together a few tried-and-true outfit “formulas” that photograph beautifully and are flattering across a wide range of body types. I’ve also included links below for each item shown, but any similar item will work, regardless of the brand.


Outfit Formula #1: Solid dress shirt + olive or tan flat-front chinos + dress shoes (+ optional: chunky cardigan)

Shirt: Express | Pants: J. Crew | Shoes: Dockers/Macy’s | Belt: Fossil/Macy’s | Cardigan: Target


I personally think this is one of the most failproof men’s outfits out there, and it works well for all seasons! Make sure your dress shirt fits properly, whether it be a slim fit or a more classic/relaxed fit, paying special attention to the shoulders. I highly recommend Express and Untuckit for their range of fits and sizes. Optional: add a chunky, shawl-collar cardigan for some cozy vibes or when the weather gets chilly.


Outfit Formula #2: Mockneck Half-zip Sweater + Dark wash slim/straight fit jeans + Chukka boots

Sweater: J. Crew | Jeans: J. Crew | Boots: Zappos | Belt: Banana Republic


I’ve been recommending mockneck sweaters to men ever since my bestie Hannah asked me to help with her fiance’s outfit for her engagement session back in college! And that’s because they offer the perfect classic and clean vibe without being too stuffy or preppy. Choose an understated fall tone such as olive, heather gray, or camel – or kick it up a notch in a rich red or burgundy!

Dark wash jeans are almost always more flattering than light wash jeans. For a more lived-in feel, try picking a pair that has a bit of light texture or distressing (though I don’t recommend too much distressing or actual holes).

Pro tip: make sure your belt color matches your shoe color as closely as possible. It will help your outfit look extra put-together! For fall outfits, I recommend brown leather instead of black.


Outfit Formula #3: Neutral slim-fit flannel shirt + Dark wash slim/straight fit jeans + oxford sneakers

Shirt: Express | Jeans: J. Crew | Shoes: Zappos | Belt: Tie Bar


Flannel can be tricky for photos since it tends to come in busy colors and plaids, which are distracting to the eye, and in slightly oversized fits that can look undone. However, sub in a solid or neutral pattern like this soft grey windowpane pattern, plus a slim fit, and you’ve got yourself an everyday, casual look that still looks polished.


Some great places to shop for men’s outfits:

J. Crew (sweaters, dress shirts, jeans, chinos, and most anything!)

Express (dress shirts, flannel, jeans)

Untuckit (dress shirts – check out their range of fits!)

American Eagle (jeans, casual button-downs, sweaters)

Everlane (sweaters)


Looking for more? Check out my women’s fall/winter outfit inspiration guide here!



Jocelyn Bravo is a Northern Virginia family photographer who specializes in creating joyful and luminous images for families and couples. She is based in Alexandria, VA and loves working with clients all across Virginia and the DMV.


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