16 Jennifer Aniston Outfits That Prove She Always Looks Good

Jennifer Anniston is a very good looking and stylish actress. We must admit, she doesn’t exactly go for unconventional, surprising or risque looks. Shocking people by wearing something outrageous isn’t really her style. She prefers to look good and stick to what suits her best. But that doesn’t mean she’s boring, this lady just knows what’s good and she’s managed to have a very successful and long career in film and never really have a fashion faux-pas. She’s always stunning. And you know, she’s Jennifer Anniston, she really doesn’t need to dress crazy to get people’s attention, everyone knows who she is no matter what she wears. She has a haircut named after her, and whenever you say that to anyone they know exactly what you mean, she’s that level of famous.

1. This is Jennifer Anniston in 1995. Can you actually believe this was 25 years ago? It seems insane. But also, you can see that Jennifer clearly had impeccable style. She knew how to rock a simple black slip dress then and that’s still stylish today. Also, we had to include the outfit from “The One Where the Monkey Gets Away” because even though it’s a styled Rachel outfit it still holds up to this day and I’d totally wear it.

2. Oh man, remember when Jennifer and Brad were the hot couple? Those were the times. Are we still holding out hope that they’ll find their way back together? We sure are. But back to Jen’s outfit. You might think “sequins, really?” but you’ve got to remember this was 1999 and let us tell you – this was the most sophisticated dress at the time. I mean, look at Brad, what are those glasses?

3. All black triangle crop top and a matching maxi dress, hell yeah Jennifer rocked that like no other. This was quite an edgy outfit at the time and definitely an edgy one for Jennifer but she pulled it off no problem.

4. Here’s another 90s classic with the square toe boots. Isn’t it amazing how cyclical fashion really is? Not to mention the whole all-black outfit that’s very trendy these days when monochrome is the way to stand out. It’s like Jen knew something we didn’t.

5. We’re entering the 2000’s now and boy did Jennifer do that with style. That leather coat and fluffy handbag combo? Very cool, very edgy, very on-trend. And the red dress is what she wore to the Emmys that year. Absolutely iconic, there’s no way around it.