How To Wear Oversized Outfits (In A Classy & Modest Way) + Outfit Ideas

Hey guys! I don’t know about you, but I love oversized sweatshirts, sweaters & tees! They just have a cozy vibe to them that I adore! 😍 However, is it just me or do you kind of find them hard to wear sometimes too? Oversized items can be a little more tricky to wear in a classy & modest way, at least in my experience, but I’ve found a couple of tips that have really helped me and I thought I’d share them with you guys today as well! πŸ™‚

Also, a huge shout-out & thank you to Layered Grace for sending me the “make heaven crowded” tee and the “summer sunshine sweatshirt” you can find the tee (mine is in watermelon) here and the sweatshirt (mine is in old gold) here. Also, I sized up for the sweatshirt (medium) to give it more of an oversized feel but the tshirt is my usual size (small). Use my code HANNAH10 at Layered Grace to get 10% off!

Now for some tips on how to wear oversized outfits in a classy & modest way:

1. Tuck in the tee. I think the easiest way to make your outfit look more structured and not sloppy is to tuck in your tee! It’s really easy to do and can be done with jeans, leggings, skirts, shorts, joggers, etc. It instantly makes you look that much more put-together and ready to take on the day!

2. Balance an oversized sweatshirt with tighter jeans or pants. If you don’t want to use the tuck in your top or are wearing something bulkier that would be hard to tuck in (like a sweatshirt) then just pair a sweatshirt with tighter jeans or pants for balance. Oversized sweatshirts are typically a little bit longer, so you can usually pull them off with skinny jeans just fine! πŸ˜‰

3. Add a long/oversized cardigan for warmth & layers. Into the fall and winter as the weather gets chilly, it can be helpful to layer a cute cardigan over a tee for more warmth and to just add a cozy oversized feel to the outfit. I like to tie up or tuck in my tee with jeans then layer a cardigan on top! Here, here and here are a couple of my favorite long/oversized cardigans for this fall!

4. Pair an oversized jean jacket with a fitted tee & black jeans (or leggings). Personally, I don’t like the look of jean jackets with denim jeans – I like the look of denim jackets with black jeans/leggings and dresses. I love the look of this basic Ralph Lauren tee with black jeans & a jean jacket. I got my jean jacket from Old Navy in medium for a more oversized and long feel.

5. Don’t wear all oversized. I brefly talked about this in tip #2, but I thought I’d make it into an entire tip because it’s super important! You need some structure in your outfit if you don’t want to look like you just rolled out of bed. If you do want to wear looser pants and a looser top, tuck the top in to add some structure! Generally though, it’s best to either wear a looser top and tighter bottoms or a more form fitting top and looser bottoms.

6. Pair with a cute midi skirt. This is something that has been super trendy recently and it is absolutely adorable! Tie up or tuck in a t-shirt with a flowy midi skirt for a casual & classy summer or fall outfit! I love how effortlessly cute this outfit is! Here and here are two of my favorite midi skirts right now!

7. Tuck in with high waisted shorts. This tip is perfect for summer or if you live in a warm climate where you can wear shorts all year long! I love tucking in an oversized tee with shorts! The one above is from Vineyard Vines and I’m usually a small but Vineyard Vines’ shirts are a pretty big. (size down one from your typical size)

Alright guys! I think that’s it! If you enjoyed this post, make sure to drop me a comment below and hit the like button! 😁

❀ Hannah

P.S. Don’t forget to share your fav outfit from this list on Pinterest!

33 thoughts on “How To Wear Oversized Outfits (In A Classy & Modest Way) + Outfit Ideas

  1. These are all such great tips!! All of the outfits are so cute and classy! And may I just say that I LOVE all of the shoes in this post (lol).
    I always have a hard time finding affordable and yet still cute, shoes/boots!!!

    Thanks for all the wonderful tips!!

    Liked by 3 people

    1. Thank you so much, Amber! πŸ™‚ Haha, I know I love shoes! I know they can be so expensive! I usually wait for sales or look at TJMaxx for discounts! πŸ™‚


  2. Great tips! I’m a big fan of the tucking in method and the wearing tighter pants with a lose top.
    Oversized sweatshirts are my favorite so this was right up with my sense of style.!

    Liked by 2 people

  3. Eeep! I need you to go shopping for me, all of your outfits are so gorgeous!! *heart eyes* And oohh! This post is super helpful for me because most of my clothes are a bit to big. XDD Wondermous post!

    -Laura ❀ πŸ™‚

    Liked by 3 people

    1. Personally, I think that it depends on the shorts and the occasion. Ripped cut-off shorts? Nope. Not distressed midi shorts? Sure, for most occasions. I usually prefer to wear high waisted shorts in the ‘midi’ length. I personally like that length far more than the cut off or “booty” shorts. I also don’t really wear jean shorts to church or other religious ceremonies, although I do wear paper bag shorts on occasion. I’d much rather wear a dress or jeans over shorts I didn’t appreciate. Those are just my thoughts though! πŸ˜‰

      Liked by 1 person

  4. This post was really cute Hannah πŸ™‚ I really liked the yellow sweatshirt and with those boots, eeeek, it was so cute! πŸ™‚ Also the make Heaven crowded t-shirt was super cute too πŸ™‚


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