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When to Wear Heeled vs Flat Chelsea Boots In An Outfit

new chelsea boots vs old chelsea boots

My favorite black Chelsea Boots are back this year in the Nordstrom Anniversary Sale. The style this year has a slightly higher heel than in years past, so here is a quick comparison of the new heeled version and the original version.

 

 

Have you shopped the Nordstrom Anniversary Sale yet? There are some fantastic pieces available that are closet staples.

One of my top closet staples that I recommend adding to your closet is a pair of BLACK CHELSEA BOOTS. These are my most worn shoes during the winter, and this year in the Nordstrom Anniversary sale, they have a new CHELSEA BOOT WITH A HIGHER STACKED HEEL.  I bought the new higher heel boot to try, and although it’s nearly identical to the older version, with just about 3/4″ higher heel, I think there are a few reasons to check out these boots and grab a pair.

Reasons I think the new heeled boots are worth adding to your closet

  • If you’re petite, the new higher heel boot is great for giving you a little extra height
  • The higher heel works really well with longer, full length jeans, trousers, and pants.
  • If you’re wearing a dressier outfit, with a sweater dress or fall skirt, a little extra height makes the outfit feel a bit dressier.

If you already have the original, I don’t necessarily think you need both. I’m keeping the heeled pair, AND I have the original, but today I’ll show you four outfits with one of each boot and show which boot works well with various outfits to help you decide which pair to add to your closet.

 

How to wear the Chelsea boots with various styles of bottoms:

chelsea boots, sezane wide leg jeans, black anthropologie top

Full length Wide Leg Jeans and Pants:

Full length, wide leg jeans and trousers are a very trendy style this year (and also a very classic style that you can continue to wear forever)!

I think the HEELED CHELSEA BOOTS are a better option for this style of jean. You can see on the FLAT side in the graphic above that the leg of my pant gets scrunched with the flat boot, rather than falling straight without bunching.

If your closet has a lot of full length, wider leg pants, you’ll for sure want a pair of the heeled boots to give you a little lift and not make your pants drag on the floor.

outfit links: SIMILAR FULL LENGTH WIDE LEG JEANS | BLACK BLOUSE WITH SWISS DOT SLEEVES | HEELED CHELSEA BOOTS | FLAT CHELSEA BOOTS | MADEWELL MOLTEN HUGGIE HOOPS

 

Chelsea boots, everlane way high straight leg jeans, anthro black blouse

Cropped Straight Leg Jeans and Pants:

Cropped, straight leg jeans and pants are probably my favorite style to wear. I think both the heeled and the flat boots work really well with this kind of pant or jean, so it makes no difference which pair you choose!

If you’re petite, then maybe the heeled boot will work better for you. If you’re taller, choose the flatter boot. Both are good options here!

outfit links: EVERLANE WAY HIGH CROPPED STRAIGHT LEG JEANS | BLACK BLOUSE WITH SWISS DOT SLEEVES | HEELED CHELSEA BOOTS | FLAT CHELSEA BOOTS | MADEWELL MOLTEN HUGGIE HOOPS

 

Anthropologie colette pants and black blouse, chelsea boots

Cropped Wide Leg Pants and Jeans:

These are my favorite cropped wide leg pants, and they work really well with the Chelsea boots! Again, I think both the heeled and the flat work really well here.

If you’re petite, then maybe the heeled boot will work better for you. If you’re taller, choose the flatter boot. Both are good options here!

outfit link: ANTHROPOLOGIE COLETTE WIDE LEG PANTS | BLACK BLOUSE WITH SWISS DOT SLEEVES | HEELED CHELSEA BOOTS | FLAT CHELSEA BOOTS | MADEWELL MOLTEN HUGGIE HOOPS

 

Target Maxi skirt, anthropologie black blouse, chelsea boots

Dressier outfits with skirts or dresses:

If you’re wearing your Chelsea boots in a dressier outfit, like a skirt or dress (maybe even with tights during the winter), the original chelsea boots totally work, but can sometimes feel a little more casual.

In this case, I think the heeled boot does feel slightly more elevated for these outfits. I would choose the heel over the flat for a sweater dress and tights outfits, or winter dress and skirt outfits.

You can see some dressier outfits I created with THE ORIGINAL CHELSEA BOOTS in THIS POST RIGHT HERE, and I think all of them work well, but the heeled would certainly feel more elevated here.

outfit link: TARGET MAXI SKIRT (wearing size XS) | BLACK BLOUSE WITH SWISS DOT SLEEVES (wearing size XS) | HEELED CHELSEA BOOTS | FLAT CHELSEA BOOTS | MADEWELL MOLTEN HUGGIE HOOPS

 

I hope that’s helpful! Both boots are on sale for 30% off right now and fully stocked, so now is a great time to grab either the HEELED VERSION or the FLAT VERSION, or both!

 

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4 Comments

  1. wants to know! says:

    Can you run this post again but without standing on carpet? I was so happy to see the post but the carpet pile obscures the differentiation between the two types of boot. please and thank you!

  2. alvinrayan says:

    Its amazing and i like it thanks.

  3. Emily says:

    Thank you for your advice. I especially like the outfit for OUTDOOR CONCERT IN THE PARK, it’s very stylish. I have a question for you, I’m currently looking for a marketplace where I can buy second-hand clothes cheaply. I accidentally found the poshmark canada marketplace on a review site, and it seems to have good reviews. Have you ever bought things on this marketplace, and can you recommend it? Thank you.

  4. Gurugram says:

    Absolutely loved your chic and practical outfit ideas for outdoor concerts! The denim dress for country vibes and the coated skirt for rock concerts are perfect picks for any summer event. Thanks for sharing these stylish yet comfortable alternatives to the usual tiny shorts. Can’t wait to try these looks!

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