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I feel like shopping online has helped my fashion sense. Before I would just walk into a store, try on the first thing that look agreeable, and if it fit I'd buy it and leave. Mostly I just wanted to get in and out. But most online retailers have lookbooks and recommendations. You get a better idea of what clothes look good with other clothes. Plus because you're in the comfort of your own home, you can take as much time you want deciding what you think looks best. Also the simple act of browsing clothes becomes a lot easier/faster. Rather than rummaging through a store you're just scrolling down a page. You can literally glance through hundreds of styles in a matter of minutes.
I think the inspiration side of it is huge - seeing how a look wears on someone else is completely different than seeing something hanging or on a mannequin. Which online retailers do it best?

Personally a huge fan of MFA on Reddit for inspiration.

"Mostly I just wanted to get in and out." Yes. I really very much hate shopping for clothes.
you've omitted the single greatest hack - actually being in shape. it makes buy clothes so much easier, most certainly when shopping online.
Haha, very true. I think that'll be the next blog - MED/tl;dr on being in shape - especially when you're time-constrained / building a company.
skipping, planks, & pushups. it won't make anyone super strong but guys can be far more fit than average. nothing worse than a fatty wearing the clothes you've described. also, MFA is fantastic.
Shopping online has made me hate shopping 100x less than I used to. I dig that its becoming increasingly easy to buy legit stuff online without having to go to a freggin mall.
The best hack is being able to just re-order when things start to look a bit shabby. Set it and forget it.
The problem is that by the time things start getting shabby you all too often find out that the manufacturer is no longer making it any more.
Excellent point. When I buy clothing online (Amazon, Everlane, etc), I try it for a week or two. If I love it, I buy several more (2-6, depending on if its shirts, pants, how much I love it, etc) and put them away in a box to pull out at some future point.
Or you order it and only after it arrives do you realize it's been completely redesigned. Different shade of whatever color it was before, different cut, different materials, etc.
I bought two pair of Levis online. Same size and style as each other, and as the pair I had at home that convinced me I wanted more. All three pairs are radically different fits. The two pair came from different suppliers, shipped by $ONLINE_RETAILER.

It's not a paradise by any means.

EDIT: this was meant to be a reply to wsul's sibling comment.

I've had the same problem before. Store shopping as well. Sometimes I'll try on two colors of the same shirt and they'll fit much differently. The fix to this though is just to find the manufacturers that understand how important consistency is. It isn't easy.. manufacturing clothes is fairly imprecise, depending on methods used, but some companies care more than others.