How to Style Oversized Sweaters

As part of my Fall Wardrobe Challenge, I’m featuring a new look each week with different styles that feel so right during the Fall. I do a new look every day on Instagram with a video with tips and tricks on how to style the outfits. Each post is linked to with suggestions for your favorite pieces. Click on the photos to check them out!

5 days – 5 outfits and here’s the round up!


We’re getting back to warmer weather here in New England again, so I’m wearing a loose knit cotton dolman sleeve sweater from Wooden Ships – it’s light, airy and doesn’t cling. These Level 99 jeans are a great skinny that allows just enough room for me to tuck my bootie under them. I just love this mustard scarf with these colors.


This is another super light cotton sweater that’s great for the Fall transition – airy, not clingy but still comfy. Because this is an extra long sweater (and with POCKETS!!) it’s perfect for leggings. As I’ve mentioned quite a bit. I’m a bit of a rocker chick so there’s usually some touch of that vibe in my look – and so…. (vegan) leather leggings and some black block heeled booties from Frye.


What’s more comfy than a warm, cuddly sweater? Boyfriend jeans AND a warm, cuddly sweater! Add a pair of Frye sneakers and you’ve got a relaxed daytime look that keeps you cozy (and stylish) all day long.


Getting down to business!

I think everyone has an idea of what is “acceptable” business wear. I bet you rarely think of an oversized sweater as part of a work wardrobe!

But they can be styled for a fun and unique business look with the right clothing. I’ve taken this Wooden Ships open knit sweater and paired it with a great wide leg trouser and oxford heels. Add a long necklace or pendant and some bracelets or a watch to turn this fun sweater into a meeting-worthy look.


 Sweater vests 

Who said oversized sweaters have to have sleeves? I love a good oversized vest for cool Fall days with a long sleeved shirt underneath. Keeps you warm but not TOO warm.

These Blank NYC were a favorite at my shop – I had to reorder full size runs twice. Embroidered jeans are so much fun and the look cute with a little bootie like these from El Naturalista – this brand uses sustainable materials and made so well. I’ve layered. Few of my favorite necklaces, including this longer key pendant. You probably already know I love to proudly state I’m a Leo, so there’s no surprise the shorter necklaces are the symbol and the Leo constellation.

Follow along with me every week on Instagram ( @styledefiner) for up-to-date styling tips and tricks!

And check out my on the app (you can grab it for your smartphone!) My handle is  @thestyledefiner 

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