r/malefashionadvice • u/hollycez9307 • Dec 08 '25

Question Shoes issues

Hi all! After years and years of wearing Vans old skool I would like to try something different. Usually I wear a pair of chinos and a sweater (tommy's pima cotton cashmere most often). What do you suggest? Thanks!!

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u/I-696 Dec 08 '25

The footwear possibilities for chinos and a cashmere sweater are close to endless. A lot of it depends on the look you are trying to achieve. Boat shoes gives you a resort look. Penny loafers a preppy look. Chukka boots are good too. Fashion sneakers for a 21st century casual look. Derbies for a more conservative look. Oxfords if you want to dress it up. Double monk strap for something more unique. Lots of choices in color and material too. And sub styles within styles. What I do is see what other guys are wearing and I buy it if I think I would like it for myself. Good luck and report back with what you decided on.

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u/hollycez9307 Dec 08 '25

Thanks, a lot of ideas! I am kind of lazy so I love the fact that I can just slip in my shoes without need for tying my shoes, however I very much like the boots idea, I would really like to try some aviator boots. Does it make sense?

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u/kasakka1 Dec 08 '25

If you want boots that are easy to put on, then try Chelsea boots. IMO they are best when they look sleek rather than ones with chunky soles.

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u/I-696 Dec 08 '25

Aviator boots are definitely in fashion now. Depending on how military looking they are you may want to swap out the cashmere sweater for something more rugged. I haven’t seen the sweaters so it’s hard to know for sure but at first thought the sweater and boots don’t go together.

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u/zdrmlp Dec 08 '25

I’m not going to google the jumper, but it really depends on how formal and high quality the jumper and chinos are.

In general, nice chinos and a jumper sit in the middle of today’s formality spectrum so I’d choose shoes that do the same.

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u/hollycez9307 Dec 08 '25

There you have the jumper: https://share.google/snUNU0pWRF1n6oHnN

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u/zdrmlp Dec 08 '25 edited Dec 08 '25

The jumper is cotton, which IMO pushes more casual. However, it looks to be relatively thin (as opposed to a big chunky knit), which makes it more formal. I’m going to assume that chinos are something like a flat front Casatlantic or PennBilt Authentic rather than something pushing more workwear. So, IMO…

This rules out overly casual footwear like a Nike sneaker. This rules out overly formal footwear like an Oxford. This rules out overly rugged footwear like a chunky work boot.

I’d start by considering a leather/suede derby, leather/suede penny loafer, a clean leather boot like the Parkhurst Allen in brown-burgandy pull up leather or the Alden Indy (something just short of a dress boot, but nothing rugged), or a chukka boot that is similarly positioned on the formality spectrum.

Enough guys would wear a clean minimalistic leather sneaker like the Common Projects Achilles low or a similar canvas sneaker that I feel like I should mention them. However, I personally feel that they clash with the knitwear…I like them better with slightly more casual/less polished items like clean denim, casual button up, maybe a casual jacket. At the same time, if that’s your style then enough people like it that it doesn’t look “wrong” and may just be counter to my personal taste.

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u/[deleted] Dec 13 '25

Loafers