How to Dress with Swag

Co-authored by Kalee Hewlett

Last Updated: February 4, 2023 References

Swag refers to the way you look and present yourself, and it comes from hip hop culture. When you dress with swag, you have a keen fashion sense and confidence in your style. People who dress with swag have a detail oriented view of their clothing that ensures they make a statement with every outfit. Dressing with swag means you are proud to show off what you’ve got.^{[1]
X
Research source}

Part 1

Part 1 of 3:

Making Over Your Wardrobe

1
Clean out your closet of all old and outdated items. Get rid of items that don’t add to your style:^{[2]
X
Research source}
- Clothes with old stains, holes, tears, or otherwise falling apart should be discarded
- Items that are no longer trendy but still in good shape can be donated to thrift stores.
- Name brand items that don't add to your swag can be sold at consignment stores to increase your budget for new clothes.
2
Pick a store to buy your clothes from. For name brand clothes you can go to the actual store and buy something, but there are other ways to get the clothes if you want to save some money. You can find new or gently used name brand clothes online from sites like eBay, craigslist, or online garage sales. Check out local thrift stores to find name brands at a fraction of the price. You can even participate in a clothing swap to give away your old clothes and get some new ones in return.

Advertisement
3
Buy some name brand items. Name brand items can signify money and power, so having a few items to wear will portray you as being successful. Mix and match with store brand items to create more outfits with swag.
- Get a few name brand shirts.
- Buy one pair of name brand pants
- Invest in a high quality name brand pair of jeans.
4
Get several classic clothing items. Having classic items in your closet to use as staples will help you easily put together outfits that have swag.^{[3]
X
Expert Source

Kalee Hewlett
Image Consultant
Expert Interview. 23 April 2019.} There are a few staple items that help create multiple outfits:
- A button down shirt
- A utility jacket
- A black dress, for girls
- Graphic Tees
- Jeans
- A hoodie
- A hat or beanie

Part 2

Part 2 of 3:

Accessorizing Your Closet

1
Buy a stylish hat. Get a hat that makes you feel confident and comfortable. Experiment with wearing your hat different ways like to the side or the back to see how it makes you look and feel. It doesn’t matter what type of hat it is so long as you feel cool in it:^{[4]
X
Research source}
- A baseball cap
- A sun hat
- A beanie
- A cowboy hat
2
Invest in a trendy pair of shoes. Shoes are a big part of an outfit and having popular shoes can be viewed as symbol of status. A name brand pair of sneakers are a definite must for dressing with swag. White sneakers are a great option because they will go with many different outfits.^{[5]
X
Research source}
- Wash or shine your shoes regularly.
- Choose a high quality pair of shoes that will last.
3
Pick out a few pieces of jewelry or a watch. Having jewelry or a watch will add a flashy element to compliment your outfit. Gold or silver chains can help make your look complete. Name brand watches are a nice touch to convey high class for both genders.^{[6]
X
Expert Source

Kalee Hewlett
Image Consultant
Expert Interview. 23 April 2019.} Kick up the swag with more jewelry:^{[7]
X
Research source}
- Large rings and earrings can add to your swag look.
- Heavy bracelets or multiple bracelets can be great for girls' swag.

Part 3

Part 3 of 3:

Researching Trends

1
Read fashion blogs to learn the latest trends in style. Use news articles to learn about urban street fashion. Find articles about the history of urban fashion as well as news from current designers. This will help you find a base to build your style from.^{[8]
X
Research source}
2
Follow Hip Hop Artists on Social Media. Use social media sites like facebook, twitter, tumblr, and instagram to follow the big players in the industry. You will see what they’re wearing and be able to emulate their current style. Pay attention to artists that have made a name for themselves in fashion industry:
- Sean Combs
- Kanye West
- Jay-Z
- Rihanna
3
Attend street festivals and concerts. See what fresh trends are on the streets today by visiting local festivals and concert venues. Check local calendars to see when popular artists will be in town to see in person what swag the stars are rocking.

Expert Q&A

Question

What should I buy if I'm updating my wardrobe and I want more swag?

Kalee Hewlett
Image Consultant
Kalee Hewlett is a Celebrity Stylist & Confidence Coach with almost two decades of experience helping clients build confidence and ‘dress for success.' She works with her clients to transform their sense of self 'from the inside out’ by merging her expertise in image consulting with Neuro-Linguistic Programming. Kalee’s work is rooted in science, style, and the understanding that ‘identity is destiny'. She uses her own methodology and Style To Success Strategy to create positive identity shifts. Kalee is a fashion TV host and appears regularly on QVC UK sharing her fashion expertise. She also was appointed as the head judge and host of Fashion One Network’s 6-part TV show 'Design Genius.’

Kalee Hewlett

Image Consultant

Expert Answer

You really want to lean heavily into the bold, playful accessories. Bags, jewelry, necklaces, cuffs, and the like all add the little textures and noise you need to make more of a statement.
Question

Why are accessories so important when it comes to style?

Kalee Hewlett
Image Consultant
Kalee Hewlett is a Celebrity Stylist & Confidence Coach with almost two decades of experience helping clients build confidence and ‘dress for success.' She works with her clients to transform their sense of self 'from the inside out’ by merging her expertise in image consulting with Neuro-Linguistic Programming. Kalee’s work is rooted in science, style, and the understanding that ‘identity is destiny'. She uses her own methodology and Style To Success Strategy to create positive identity shifts. Kalee is a fashion TV host and appears regularly on QVC UK sharing her fashion expertise. She also was appointed as the head judge and host of Fashion One Network’s 6-part TV show 'Design Genius.’

Kalee Hewlett

Image Consultant

Expert Answer

Accessories are really what transform an outfit. They can turn a boring old capsule closet into something really playful and unique.
Question

Should I replace all of my old jewelry if I want to overhaul my wardrobe?

Kalee Hewlett
Image Consultant
Kalee Hewlett is a Celebrity Stylist & Confidence Coach with almost two decades of experience helping clients build confidence and ‘dress for success.' She works with her clients to transform their sense of self 'from the inside out’ by merging her expertise in image consulting with Neuro-Linguistic Programming. Kalee’s work is rooted in science, style, and the understanding that ‘identity is destiny'. She uses her own methodology and Style To Success Strategy to create positive identity shifts. Kalee is a fashion TV host and appears regularly on QVC UK sharing her fashion expertise. She also was appointed as the head judge and host of Fashion One Network’s 6-part TV show 'Design Genius.’

Kalee Hewlett

Image Consultant

Expert Answer

No, you can definitely hang on to your old jewelry unless you aren't a fan of it in the first place. Jewelry can dramatically change an outfit, and you can wear it over and over again with different styles, so I wouldn't just get rid of everything you own.