Winter Outfits with Flare Jeans

The Millennial in me loves seeing the return of flare and bootcut jeans. They give the illusion of longer legs – so for the short gals out there like me – flare jeans are a friend. The ’03 Bootcut Jeans from J.Crew were my most worn pair of jeans this fall, but the ’96 flare jeans may be taking their place. These flares have a slim fit and a fairly dramatic flare. I sized down per the reviews and although they’re tight at first, they loosen with wear – so a size down is a good call.

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Winter Outfits with Flare Jeans

My Sizing: I’m 4’10”, and my bust, waist, and hip measurements are 32″, 24″, and 36″. My inseam is 25″ (the measurement from the inside of my leg to my ankle bone). The clothes shown are unaltered and show how they fit me right from the store. I list my sizing beside each item to help you compare when shopping online. When referencing my true size, that is often the smallest option available at a brand or petite xxs/00/24. I wear a size 5 shoe.

*The jeans in this post sold out quickly, but I’m watching for a restock. They’re a newer release for J.Crew so I anticipate they will come out in more washes!

Trench Coat

If you’re looking for a trench coat to add to your wardrobe my top pick is the Icon Trench from J.Crew. It has the best petite fit. It’s not overwhelming, I find the above the knee length to be not only the best for petites, but it’s a classic length that never goes out of style. It’s true to size overall, but does run slim through the sleeves. The sweater I’m wearing under the jacket I passed on several times before ordering it. On the model it looks like it’s really long in the sleeves and oversized, but I read the reviews and a lot of petite ladies were singing it’s praises. In person it’s prefect! The sleeves are thick but they’re a great length and it’s perfectly cropped. The model has to be wearing it two sizes large.

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Jacket Petite 00 | Jeans Petite 23 | Sweater XXS | Layering T-Shirt XS | Boots | Bag | Earrings

Puffer Coat

The jeans are a tiny bit long with flats, but I don’t mind a little bit of bunching (it’s on-trend to wear your jeans a little bunchy). I paired them with high-top converse here, my personal favorite slim sneaker. This look can also be accomplished with sneakers like Adidas Sambas (I just prefer the converse over them). The sweatshirt is a perfect cropped length for petites, I just have the waistband cuffed under, not tucked in. I paired it with a cropped puffer jacket from Quince. This coat rivals my Aritzia Super Puff! Comparing the two, they’re almost identical, the Aritzia coat is slightly warmer, but for 1/2 the price, this coat is a great option.

Jeans Petite 23 | Layering T-Shirt XS | Coat XS faded cargo | Bag | Sweatshirt Petite XS | Sneakers

With a Long Cardigan

In Lexie Kay wash the jeans have pockets on the front and slash pockets on the back. It gives them a trouser jeans look! This pair is currently on pre-order and worth the wait. I find this pair to fit a little bit looser than the lighter wash, so definitely size down here. I paired them with the Shrunken Cashmere Sweatshirt from Quince and a long caridigan from Amazon. The Amazon cardigan is a great dupe for my J.Crew Juliette sweater. It’s similar in fit, starting at XS it is a little bit larger on me (the juliette cardigan comes in xxs) but in my opinion it’s a good enough fit!

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Layering T-Shirt XS | Sweater XS | Cardigan XS apricot | Boots | Bag | Belt | Earrings

With a Blazer

I restyled the herringbone blazer from the Winter Workwear Capsule Post for this outfit. I originally styled it with flats and then checked myself for how unrealistic that is for winter weather and restyled it with boots (unless you’re one of my friends who lives somewhere warm).

Jeans Petite 23 | Sweater XXS | Layering T-Shirt XS | Blazer Petite 00 | Boots | Bag | Flats | Earrings | Belt

Cozy Sweater

I’ve had this sweater hanging on my rack for the last month and meant to style it. It’s so thick and warm, but unfortunately I waited too long and my exact color sold out. I’m still seeing it available in navy, which I think would look great with the jeans as well.

Petite-friendly winter outfits with flare jeans via pumps and push-ups blog | petite friendly winter outfits | petite style | casual winter outfits

Jeans Petite 23 | Sweater XXS | Layering T-Shirt XS | Boots | Bag | Earrings

-Brooke

Brooke of Pumps and Push-Ups - petite style blogger

Hello, I'm Brooke!

A petite (4'10") gal on the hunt for the best petite clothes. I show you where to shop for petite finds, and how to style them in my weekly style sessions. I don't alter or hem any of the clothing on my blog - what you see is exactly how the items fit me right from the store.

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