Winter is coming and my footwear is not ready. I need a pair of boots that I can wear with a business suit on a walk to lunch without looking totally out of place. So a winter Chelsea boot it is. Here are some options in different price points.
Elected Official

Legislative Aide

Front Desk

Wide Boots

Naturalizer Darry Bootie ($168)
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What kind of ankle boot would you suggest for tights + dress + jacket or skirt + sweater in a “smart casual” environment?
Indoor or outdoor?
I have these and have loved them for the last several years. I think they were an Abra rec from several years ago? https://www.dsw.com/product/blondo-valli-waterproof-bootie/566232?activeColor=005&size=8.5&width=Medium&cm_mmc=CSE-_-GPS-_-G_Shopping_PLA_PMAX_Boots_Booties-_-&cadevice=c&gclsrc=aw.ds&gad_source=4&gad_campaignid=21497709831&gbraid=0AAAAADRIb9SG42zuyoS5nE5lvbBvF7VT2&gclid=Cj0KCQiAwdDXBhDuARIsAFdLukkOqfdYTox1oBXepjuH719GHx3i2cAIGEqICq9f4vFi0WFlixjQz9waApp6EALw_wcB
If you have feet issues, I highly recommend the Birkenstock suede Chelsea. I recently wore them all over London sightseeing without any pain, which is unheard of for me and boots. I treated them before we left and they look brand new even after 5 days in the driving London rain.
+1 for the Birkenstock Chelsea! I’ve had mine for years and have put literally hundreds of miles on them. They’re great.
What pants are we wearing with these? I have a hard time with the not ankle/not knee high look.
Wider leg pants.
I struggle SO hard with this!
Would love to see a three ways post with these please!!