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If you’re a guy, you can’t go wrong with lululemon. They have slacks and dress shirts - super comfy
Yes their commission pant is my go to for going out. Comfy and dressy, also live in DC and just add a basic tshirt and you should be good to go
Take a closer look at people around you. When you see someone wearing something you like, take a closer look. How have they put their outfit together? Could you recreate it more or less with the clothes you have? What would be missing? Try to look for these specific items - go for things you'll wear frequently. E.g. when you are out, you're wearing jackets most of the time. Look for jacket styles you like. Consider what goes with the shoes you have and the type of pants you like to wear. Make sure it works with many things in your wardrobe. Then purchase the right one - it's 50% of your outfit, if you made sure it goes with most of your trousers and shoes, you're set!
You can also turn to fashion influencers to see how they compose outfits, probs the easiest to browse for new inspo.
Another tip is to "challenge" yourself for a couple of days to not just leave the house wearing the next best thing. Take 10 minutes to look into your wardrobe. Combine things newly. Try them on, take it off, and try something different.
Practice this consistently even when doing groceries or whatever (not forever!). But it will get you in the hang of composing outfits and expand your "known fits" that you can then always go back to, e.g. knowing these jeans work great with that shirt.
Not to be presumptuous but this post sounds like you’re a guy? Lululemon and Bylt are great fitting and have lots of great staple items (not just athletic wear) to build a good wardrobe for men
Abercrombie and fitch should get you turned around quickly
If you’re a guy, order some T-shirts from Cuts clothing. They have a great selection of plain colors and the shirts have a very nice, athletic fit. Even if you’re not super fit, they accentuate all the right areas. Great, simple option and always get compliments when going out. A little pricey, but the quality is definitely worth it. If you want a very similar option, but cheaper, look up BYLT basics, very similar collection.
BYLT*
Live in DC as well, graduated over a year ago. I wear sweat pants and random shirts out, anything makes me feel comfortable in. Recommend start shopping in stores to know which ones fit or make you feel comfy the most.
I like Los Angeles apparel
I struggled post undergrad to redefine and refresh my wardrobe and style. I started by going online and exploring what was trending as well as what some classics were. I developed an almost ideal look book that had outfit combinations I really liked, and I also looked at what staple pieces I needed that would work across multiple fits. Then I just shopped each month, exploring different stores and trying to get that look book into my closet. It takes time but try to find inspiration and don’t be afraid to try something new!
Everlane
J crew for shorts and shirts, banana republic for chinos, Ralph Lauren for polos, Patagonia for outerwear. You can mix and match pieces for multiple outfits. Definitely hit up tjmaxx or your closest outlet mall for deals