My partner loves comfort over everything but also enjoys me helping him update his wardrobe. For background this is a man that for periods of time was homeless or had little to no money to spend on himself verses survival. Buying clothing was the last thing on his mind for the entirety of his adult life.

When I had met him he was beginning to get on the right track and now years later he is back in school and busting his ass for a better life.

I have been helping him build a solid minimalist wardrobe of good quality items which he has absolutely appreciated and has done wonders for his self confidence. One area that I’m stumped on is finding a good pair of comfy sneakers to dress up or down. For example, I bought him grey canvas and leather vans for his birthday. He loved these shoes but for casual everyday wear I could tell that they were not comfortable at all for him.

I would really appreciate any suggestions…. Comfort being most important but also versatility and quality*.

Thanks so much for your help!

9 comments

  1. ASICS, NB

    Could also go with a more casually finished dress show from a company like Allen Edmonds. Can fill the casual times dressy outfits and are incredibly comfortable once broken in

  3. I usually wear Air Max 95s and I’d recommend giving them a shot. There are so many color combinations available that I’m sure you can find something he likes.

  4. Clae is a severely underrated shoe brand. Check out the Bradley. Super high quality and can be casual or dressed up and look great. For the gym, I’m all in on the New Balance FreshFoam’s, but even the classic 574’s feel great.

  5. I wear Sperry these days for every day shoes. Bates makes some incredibly comfy boots and even tactical shoes. I’ve been working and playing in Bates for years now. Had one pair last me 5 years for $85. I’ve also got a pair of black leather formal boots. They go great with black chinos and a button down shirt. I have some brown leather work boots by caterpillar that I wear with tan canvas work pants and a comfy shirt.

    If I could only own a single pair of shoes it would be the Bates tactical shoes. Not the fanciest, but by far the comfiest and most versatile and practical. I wear my grey canvas Sperrys more than any of my other shoes in warm weather though.

  6. Adidas NMDs. They are comfortable, good quality, and majority of the designs look good. Also good price range from 100usd-160usd.

  7. Cheap Kmart runners. Literally $10 – 15 a pair last 6 months.

    My partner loves her cloud flyers

  8. [Classic Adidas Stan Smith](https://www.adidas.com/us/stan_smith?af_channel=Search&af_click_lookback=30d&af_reengagement_window=30d&c=Stan_Smith-B-Exact-2-Mobile_New&cm_mmc=AdieSEM_Google-_-Stan_Smith-B-Exact-2-Mobile_New-_-General-Stan_Smith-X-General-Exact-_-43700049272966866&cm_mmca1=US&cm_mmca2=&ds_agid=58700004389691616&gbraid=0AAAAADrRVUg3ckC6lHT3-Snc_jLn2s6Uo&gbraid=0AAAAADrRVUg3ckC6lHT3-Snc_jLn2s6Uo&gclid=Cj0KCQjw–2aBhD5ARIsALiRlwBTx6iJF5n88W76Oos_xBKNyDeQo3-V5Gjq-2fmVeQFkGv56G7PrCsaAlpvEALw_wcB&gclsrc=aw.ds&is_retargeting=true&pid=googleadwords_temp)

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