Who wouldn’t want to wear a comfy sweatshirt out for a casual date night? I DON’T KNOW. I found this fun bright blue one and I’ve been wearing it non-stop. It’s that in between weather time of year where it’s still quite cool but if you’re like me you’re getting sick of sweaters and all the layers…

Cue the cozy sweatshirt in a bright color with plenty of fun accessories. Pair it with favorite black jeans, fun shoes, earrings and a bag with some metal details. This easy look could obviously be great for a day to night look, too.

I think the trick here is to choose a top that’s oversized for that sexy 80’s Flashdance vibe. That makes it more date night appropriate yeah? The bright color also helps.

And when you go out and wind up eating ALL THE SOUP DUMPLINGS no one will ever know in your oversized sweatshirt. #winning (Yes, that was me staring lovingly at our delicious meal at XLB in N. Portland)

Outfit Details

Sweatshirt – H&M Oversized Sweatshirt – So easy and comfy and you’ll probably just want to sleep in it, too. I feel like that’s the best kind of top for me these days. #easy Wearing size S.

Jeans – Madewell 9″ High Rise Skinny Jeans in Black Sea – Favorite black skinny jeans. They hold their shape and are soft and comfy. They just fit me best and the knee distressing hits where I like. I wear these literally every other day. Fit TTS.

Boots – Matisse Nelson Bootie – LOVE these. The heel height is SO walkable and yet they’re nice and dressy. They don’t come up too high on the ankle either, so they’re flattering for shorter legs like mine. I wear these as a neutral boot and I love love them. Fit TTS

Earrings – Betsy & Iya Novi Hoop Earrings – Local Portland designers and my fav earrings.

Bag – Vince Camuto Crossbody – Mine is an older style but I’m loving this updated one with similar brass details…and this one with studs is on sale!

Shop Fun Oversized Sweatshirts

Do you have a favorite cozy but date-night-appropriate shirt you love? Please send. Cozy date nights are the best!



Be sure to follow me on Instagram @elletrain to see daily outfits, what I’m currently whipping up in the kitchen, and of course, Sienna’s dance moves. Photos by the lovely Posy Quarterman Photography


  1. You gals can make a post out of LITERALLY anything. A shapeless sweatshirt? It’s not sexy oversized – it’s just way too big and completely unattractive. Those sleeves – Laura – look closer at the pics – only 16 year olds wear sweatshirts this way – and only in bed. Pretty frivolous and waste of post. Sorry but true.

    • You state your opinion like it’s a fact. You’re allowed not to like things, but don’t you think you’re being kind of rude about it? Not for you and move on. To each their own. Laura obviously thinks (see what I did there? It’s an opinion!) and so do I (and I’m 16 x 2). Love this look, Laura! Recently bought a blush sweatshirt from the men’s section at H&M and love how cozy and cute it is.

    • I personally think this is a fun, simple, cozy look! We don’t all have to be decked out super models all of the time. I love the variety that TME gives us. And by the way, this is all free (and great!) content that they put out all the time, so if you don’t like it, then don’t read it and skip leaving mean comments! Keep rockin’ your awesome looks, Laura! We appreciate your work. 🙂

  2. Love this! And now I really want the pale green H&M sweatshirt. And to answer your question…I recently ordered the Gibson Convertible Neckline Cozy Fleece Tunic (had to look that name up) that Shana has posted a few times. It’s the best! I wear it with jeans for a chill date night or with my Lysee faux leather leggings (I think that one’s a “thank you Scotti”) when I want to spice it up but still be comfy. Off the shoulders with leather pants! It kills! And still feels like PJs! I feel a pale green sweatshirt and Madewell denim date night comin on…

Leave a Reply