5 Ways to Style Overalls Winter Through Summer

5-Ways-to-Style-Overalls-for-Winter-Through-Summer

If you’ve been a long-time reader then you know I have a soft spot for overalls and believe that they can be worn stylishly at any age, and any time of year. You can see how I’ve styled them in the past HERE and HERE.

The trick is finding a pair with a tailored, figure-flattering fit. Today I’m sharing 5 ways to style overalls winter through summer. Just like finding a good pair of jeans, finding a pair of great fitting overalls can make you feel like a million bucks. 

The pair of overalls that I’m wearing here are from Madewell. I usually wear a size 26 or 27 in Madewell jeans and am wearing a small in the overalls. I also tried on the size medium, which fit, but I prefer the slimmer fit of the small. This is last year’s wash but the fit of this year’s version is the same.

These are the holy grail of overalls in terms of the quality fit and the fact that they are flattering on literally any body shape or size. However, I am also linking a dupe below.

5 Ways to Style Overalls Winter Through Summer

MY SIZING

For reference, I’m 5’7″ with a long torso and long legs. I typically wear a 27 in jeans or a size 4. My bra size is a 34D, and I typically wear a size medium top but sometimes size down for a more tailored fit or a large for a more oversized fit. If I own the item I will always list my size and any recommendations I have for sizing up or down for quick reference. (TTS= true to size!)

Add a cardigan and booties.

5-Ways-to-Style-Overalls-for-Winter-Through-Summer

Overalls (I wear a small and I’m a 26 or 27 in Madewell jeans), HERE is a really good dupe (I wear a 4 in this pair) || similar tee (I wear a medium) || cardigan (wearing a medium) || similar booties TTS

Adding a super soft cardigan and booties is a cozy way to style overalls in the colder months. I also love how this layered look mixes textures to create interest.

Or a moto jacket and sneakers.

overalls and a moto jacket

Overalls (I wear a small and I’m a 26 or 27 in Madewell jeans), HERE is a really good dupe (I wear a 4 in this pair) || similar tee (I wear a medium) || similar moto jacket (the same brand, I wear a medium) || sneakersawesome dupe option HERE

I swapped out the cardigan and booties for an edgy moto jacket and sneakers. This laid back look is equal parts comfy and cool.

Layered over a printed and fitted long sleeve tee.

how to wear overalls over 40, the most flattering overalls

Overalls (I wear a small and I’m a 26 or 27 in Madewell jeans), HERE is a really good dupe (I wear a 4 in this pair) || leopard henley (wearing a medium) || sneakers (follow the size chart) || barrette

Layering over a printed tee with sneakers is a another cute casual outfit that can be worn into spring. Leopard, stripes and polka dots are all fun print ideas.

Or a short sleeve tee with flat sandals.

5 Ways to Style Overalls for Winter Through Summer, spring overall outfit

Overalls (I wear a small and I’m a 26 or 27 in Madewell jeans), HERE is a really good dupe (I wear a 4 in this pair) || tee (wearing a small) || utility shirt || sandals || barrette

A simple tee with flat sandals is probably the most common way I style overalls. Adding a button-down tied around the waist creates some definition. And if you get chilly, just throw the top on for a cute layered look.

Dress them up with a girlie blouse.

5 Ways to Style Overalls for Winter Through Summer, dressed up overall outfit

Overalls (I wear a small and I’m a 26 or 27 in Madewell jeans), HERE is a really good dupe (I wear a 4 in this pair) || ruffle top (I sized up to a large for length), love this one and this one || wedges TTS || bag || barrette

Don’t be afraid to dress up your overalls! Pairing them with a blouse with fun and feminine details is perfect for a date night or brunch. A pair of wedges is the perfect finishing touch.

Do you have a pair of overalls? How do you like to style them?